Ascorbic Acid-mediated Reactions in Organic Synthesis

Haytowitz, D.B. Information from USDA’s nutrient data book. J. Nutr., 1995, 125(7), 1952-1955.
[http://dx.doi.org/10.1093/jn/125.7.1952] [PMID: 7616313]

Nishikimi, M.; Fukuyama, R.; Minoshima, S.; Shimizu, N.; Yagi, K. Cloning and chromosomal mapping of the human nonfunctional gene for L-gulono-gamma-lactone oxidase, the enzyme for L-ascorbic acid biosynthesis missing in man. J. Biol. Chem., 1994, 269(18), 13685-13688.
[PMID: 8175804]

(a) Svirbely, J.L.; Szent-Györgyi, A. The chemical nature of vitamin C. Biochem. J., 1933, 27(1), 279-285.
[PMID: 16745082]
(b)Buettner, G.R.; Schafer, F.Q. Albert, Szent-Györgyi. Vitamin C identification. Biochemist (Lond.), 2006, 28, 31-33.

(a) Velisek, J.; Cejpek, K. Biosynthesis of food constituents: Vitamins. Water-soluble vitamins, part 2-A review. Czech J. Food Sci., 2007, 25, 49-64.
[http://dx.doi.org/10.17221/756-CJFS]
(b)Elmore, A.R. Final report of the safety assessment of l-ascorbic acid, calcium ascorbate, magnesium ascorbate, magnesium ascorbyl phosphate, sodium ascorbate, and sodium ascorbyl phosphate as used in cosmetics. Int. J. Toxicol., 2005, 24(Suppl. 2), 51-111.
[http://dx.doi.org/10.1080/10915810590953851] [PMID: 16154915]

(a) Galesso, M.; Gatta, M.; Galiano, F. Comparative studies on the stability of ascorbic acid and its derivatives in various matrixes and interaction with commonly used cosmetic preservatives. Cosmet Toiletries Journal., 1993, 2, 58-74.
(b)Mehlhorn, R.J. Ascorbate- and dehydroascorbic acid-mediated reduction of free radicals in the human erythrocyte. J. Biol. Chem., 1991, 266(5), 2724-2731.
[PMID: 1993652]
(c)Tripathi, R.P.; Singh, B.; Bisht, S.S.; Pandey, J. L-Ascorbic acid in Organic Synthesis: An Overview. Curr. Org. Chem., 2009, 13, 99-122.
[http://dx.doi.org/10.2174/138527209787193792]

Uri, N. Autoxidation and Antioxidants, 3rd ed; Interscience Publishers Inc.: New York, 1961, Vol. I, pp. 55-106.

Higdon, J.V.; Frei, B. Vitamin C: an introduction In: The antioxidants C and E, 1st ed; Packer, L.; Traber, M.G.; Kraemer, K.; Frei, B., Eds.; AOCS Press, Santa Barbara: California, 2002.

Calcutt, G. The formation of hydrogen peroxide during the autoxidation of ascorbic acid. Experientia, 1951, 7(1), 26.
[http://dx.doi.org/10.1007/BF02165477] [PMID: 14813261]

(a) Bielski, B.H.J. Chemistry of ascorbic acid radicals.Ascorbic Acid: Chemistry, Metabolism, and Uses; Seib, P.A; Tolbert, B.M., Ed.; American Chemical Society: Washington, D.C, 1982, Vol. 200, pp. 81-100.
[http://dx.doi.org/10.1021/ba-1982-0200.ch004]
(b)Buettner, G.R.; Jurkiewicz, B.A. Catalytic metals, ascorbate and free radicals: combinations to avoid. Radiat. Res., 1996, 145(5), 532-541.
[http://dx.doi.org/10.2307/3579271] [PMID: 8619018]
(c)Buettner, G.R. In the absence of catalytic metals ascorbate does not autoxidize at pH 7: ascorbate as a test for catalytic metals. J. Biochem. Biophys. Methods, 1988, 16(1), 27-40.
[http://dx.doi.org/10.1016/0165-022X(88)90100-5] [PMID: 3135299]
(d)Song, Y.; Buettner, G.R. Thermodynamic and kinetic considerations for the reaction of semiquinone radicals to form superoxide and hydrogen peroxide. Free Radic. Biol. Med., 2010, 49(6), 919-962.
[http://dx.doi.org/10.1016/j.freeradbiomed.2010.05.009] [PMID: 20493944]
(e)Williams, N.H.; Yandell, J.K. Outer-sphere electron-transfer reactions of ascorbate anions. Aust. J. Chem., 1982, 35, 1133-1144.
[http://dx.doi.org/10.1071/CH9821133]

(a) Khan, M.M.; Martell, A.E. Metal ion and metal chelate catalyzed oxidation of ascorbic acid by molecular oxygen. II. Cupric and ferric chelate catalyzed oxidation. J. Am. Chem. Soc., 1967, 89(26), 7104-7111.
[http://dx.doi.org/10.1021/ja01002a046] [PMID: 6064355]
(b)Udenfriend, S.; Clark, C.T.; Axelrod, J.; Brodie, B.B. Ascorbic acid in aromatic hydroxylation. I. A model system for aromatic hydroxylation. J. Biol. Chem., 1954, 208(2), 731-739.
[PMID: 13174582]

(a) Halliwell, B. Vitamin C: poison, prophylactic or panacea? Trends Biochem. Sci., 1999, 24(7), 255-259.
[http://dx.doi.org/10.1016/S0968-0004(99)01418-8] [PMID: 10390611]
(b)Frei, B.; Lawson, S. Vitamin C and cancer revisited. Proc. Natl. Acad. Sci. USA, 2008, 105(32), 11037-11038.
[http://dx.doi.org/10.1073/pnas.0806433105] [PMID: 18682554]

(a) George, M.V.; Balachandran, K.S. Chem. Rev., 1975, 75, 491.
[http://dx.doi.org/10.1021/cr60296a004]
(b)Samec, J.S.; Ell, A.H.; Bäckvall, J-E. Efficient ruthenium-catalyzed aerobic oxidation of amines by using a biomimetic coupled catalytic system. Chemistry, 2005, 11(8), 2327-2334.
[http://dx.doi.org/10.1002/chem.200401082] [PMID: 15706621]
(c)Murahashi, S-I.; Okano, Y.; Sato, H.; Nakae, T.; Komiya, N. Synlett, 2007, 1675.
[http://dx.doi.org/10.1055/s-2007-984515]
(d)Suzuki, K.; Watanabe, T.; Murahashi, S-I. Aerobic oxidation of primary amines to oximes catalyzed by DPPH and WO3/Al2O3. Angew. Chem. Int. Ed., 2008, 47, 2079.
[http://dx.doi.org/10.1002/anie.200705002]
(e)Murahashi, S.; Zhang, D. Ruthenium catalyzed biomimetic oxidation in organic synthesis inspired by cytochrome P-450. Chem. Soc. Rev., 2008, 37(8), 1490-1501.
[http://dx.doi.org/10.1039/b706709g] [PMID: 18648675]

Srogl, J.; Voltrova, S. Copper/ascorbic acid dyad as a catalytic system for selective aerobic oxidation of amines. Org. Lett., 2009, 11(4), 843-845.
[http://dx.doi.org/10.1021/ol802715c] [PMID: 19146453]

Punniyamurthy, T.; Velusamy, S.; Iqbal, J. Recent advances in transition metal catalyzed oxidation of organic substrates with molecular oxygen. Chem. Rev., 2005, 105(6), 2329-2363.
[http://dx.doi.org/10.1021/cr050523v] [PMID: 15941216]

Martinek, M.; Korf, M.; Srogl, J. Ascorbate mediated copper catalyzed reductive cross-coupling of disulfides with aryl iodides. Chem. Commun. (Camb.), 2010, 46(24), 4387-4389.
[http://dx.doi.org/10.1039/c002725a] [PMID: 20461276]

(a) Nalame, N.; Chaisri, W.; Suriyasathaporn, W. Loss of L-ascorbic acid in commercial drinking milk caused by milk processing and storage times. Southeast Asian J. Trop. Med. Public Health, 2009, 40(4), 848-851.
[PMID: 19842423]
(b)Attanasi, O.A.; Favi, G.; Filippone, P.; Mantellini, F.; Moscatelli, G.; Perrulli, F.R. Copper(II)/copper(I)-catalyzed aza-Michael addition/click reaction of in situ generated α-azidohydrazones: synthesis of novel pyrazolone-triazole framework. Org. Lett., 2010, 12(3), 468-471.
[http://dx.doi.org/10.1021/ol902642z] [PMID: 20043624]

(a) Clark, A.J. Atom transfer radical cyclisation reactions mediated by copper complexes. Chem. Soc. Rev., 2002, 31(1), 1-11.
[http://dx.doi.org/10.1039/b107811a] [PMID: 12108978]
(b)Kharasch, M.S.; Engelmann, H.; Mayo, F.R. The Peroxide effect in the addition of reagents to unsaturated compounds. XV. The addition of hydrogen bromide to 1-and 2-bromo-and chloropropenes. J. Org. Chem., 1937, 2, 288-302.
[http://dx.doi.org/10.1021/jo01226a011]
(c)Eckenhoff, W.T.; Pintauer, T. Copper catalyzed atom transfer radical addition (ATRA) and cyclization (ATRC) reactions in the presence of reducing agents. Catal. Rev., Sci. Eng., 2010, 52, 1-59.
[http://dx.doi.org/10.1080/01614940903238759]
(d)Kharasch, M.S.; Urry, W.H.; Jensen, E.V. Addition of derivatives of chlorinated acetic acids to olefins. J. Am. Chem. Soc., 1945, 67, 1626-1626.
[http://dx.doi.org/10.1021/ja01225a517]

(a) Iqbal, J.; Bhatia, B.; Nayyar, N.K. Transition metal-promoted free-radical reactions in organic synthesis: The formation of carbon-carbon bonds. Chem. Rev., 1994, 94, 519-564.
[http://dx.doi.org/10.1021/cr00026a008]
(b)Gossage, R.A.; De Kuil, L.A.V.; Van Koten, G. Diaminoarylnickel(II) “Pincer” complexes: Mechanistic considerations in the kharasch addition reaction, controlled polymerization, and dendrimeric transition metal catalysts. Acc. Chem. Res., 1998, 31, 423-431.
[http://dx.doi.org/10.1021/ar970221i]
(c)Minisci, F. Free-radical additions to olefins in the presence of redox systems. Acc. Chem. Res., 1975, 8, 165-171.
[http://dx.doi.org/10.1021/ar50089a004]

Taylor, M.J.W.; Eckenhoff, W.T.; Pintauer, T. Copper-catalyzed atom transfer radical addition (ATRA) and cyclization (ATRC) reactions in the presence of environmentally benign ascorbic acid as a reducing agent. Dalton Trans., 2010, 39(47), 11475-11482.
[http://dx.doi.org/10.1039/c0dt01157f] [PMID: 20981391]

Eckenhoff, W.T.; Pintauer, T. Atom transfer radical addition in the presence of catalytic amounts of copper(I/II) complexes with tris(2-pyridylmethyl)amine. Inorg. Chem., 2007, 46(15), 5844-5846.
[http://dx.doi.org/10.1021/ic700908m] [PMID: 17602555]

(a) Min, K.; Gao, H.; Matyjaszewski, K. Use of Ascorbic Acid as Reducing Agent for Synthesis of Well-Defined Polymers by ARGET ATRP. Macromolecules, 2007, 40, 1789-1791.
[http://dx.doi.org/10.1021/ma0702041]
(b)Min, K. Jakubowski, W.; Matyjaszewski, K. AGET ATRP in the Presence of Air in Miniemulsion and in Bulk. Macromol. Rapid Commun., 2006, 27, 594-598.
[http://dx.doi.org/10.1002/marc.200600060]
(c)Oh, J.K.; Min, K.; Matyjaszewski, K. Preparation of Poly(oligo(ethylene glycol) monomethyl ether methacrylate) by Homogeneous Aqueous AGET ATRP. Macromolecules, 2006, 39, 3161-3167.
[http://dx.doi.org/10.1021/ma060258v]

Casolari, R.; Felluga, F.; Frenna, V.; Ghelfi, F.; Pagnoni, U.M.; Parsons, A.F.; Spinelli, D. A green way to g-lactams through a copper catalyzed ARGET-ATRC in ethanol and in the presence of ascorbic acid. Tetrahedron, 2011, 67, 408-416.
[http://dx.doi.org/10.1016/j.tet.2010.11.025]

(a) Vogt, P.F.; Gerulis, J.J. Amines, Aromatic.Ullmann’s Encyclopedia of Industrial Chemistry; Wiley-VCH: Weinheim, 2005.
(b)Hunger, K. Industry Dyes: Chemistry, Properties and Applications; Wiley-VCH: Weinheim, 2003.
(c)Rappoport, Z. Chemistry of Anilines, Part 1 In: Patai Series; Rappoport, Z., Ed.; The Chemistry of Functional GroupsJohn Wiley & Sons Ltd: Chichester: West Sussex, 2007.
(d)Lawrence, S.A. Amines: Synthesis, Properties and Application; Cambridge University Press: Cambridge, 2004.

(a) Jaime-Figueroa, S.; Liu, Y.; Muchowski, J.M.; Putman, D.G. Allyl amines as ammonia equivalents in the preparation of anilines and heteroarylamines. Tetrahedron Lett., 1998, 39, 1313-1316.
[http://dx.doi.org/10.1016/S0040-4039(97)10877-2]
(b)Mann, G.; Hartwig, J.F.; Driver, M.S.; Fernandez-Rivas, C. Palladium-Catalyzed C−N(sp2) Bond Formation: N-Arylation of Aromatic and Unsaturated Nitrogen and the Reductive Elimination Chemistry of Palladium Azolyl and Methyleneamido Complexes. J. Am. Chem. Soc., 1998, 120, 827-828.
[http://dx.doi.org/10.1021/ja973524g]
(c)Kiyomori, A.; Marcoux, J.; Buchwald, S.L. An efficient copper-catalyzed coupling of aryl halides with imidazoles. Tetrahedron Lett., 1999, 40, 2657-2660.
[http://dx.doi.org/10.1016/S0040-4039(99)00291-9]
(d)Grasa, G.A.; Viciu, M.S.; Huang, J.; Nolan, S.P. Amination reactions of aryl halides with nitrogen-containing reagents mediated by palladium/imidazolium salt systems. J. Org. Chem., 2001, 66(23), 7729-7737.
[http://dx.doi.org/10.1021/jo010613+] [PMID: 11701028]
(e)Barluenga, J.; Aznar, F.; Valdés, C. N-trialkylsilylimines as coupling partners for pd-catalyzed C[bond]N-forming reactions: one-step synthesis of imines and azadienes from aryl and alkenyl bromides. Angew. Chem. Int. Ed. Engl., 2004, 43(3), 343-345.
[http://dx.doi.org/10.1002/anie.200352808] [PMID: 14705093]
(f)Xu, L.; Zhu, D.; Wu, F.; Wang, R.; Wan, B. Mild and efficient copper-catalyzed N-arylation of alkylamines and N–H heterocycles using an oxime-phosphine oxide ligand. Tetrahedron, 2005, 61, 6553-6560.
[http://dx.doi.org/10.1016/j.tet.2005.04.053]
(g)Altman, R.A.; Fors, B.P.; Buchwald, S.L. Pd-catalyzed amination reactions of aryl halides using bulky biarylmonophosphine ligands. Nat. Protoc., 2007, 2(11), 2881-2887.
[http://dx.doi.org/10.1038/nprot.2007.414] [PMID: 18007623]
(h)Ogata, T.; Hartwig, J.F. Palladium-catalyzed amination of aryl and heteroaryl tosylates at room temperature. J. Am. Chem. Soc., 2008, 130(42), 13848-13849.
[http://dx.doi.org/10.1021/ja805810p] [PMID: 18811161]
(i)Zhao, H.; Fu, H.; Qiao, R. Copper-catalyzed direct amination of ortho-functionalized haloarenes with sodium azide as the amino source. J. Org. Chem., 2010, 75(10), 3311-3316.
[http://dx.doi.org/10.1021/jo100345t] [PMID: 20359203]
(j)Senra, J.D.; Aguiara, L.C.S.; Simas, A.B.C. Recent Progress in Transition-Metal-Catalyzed C-N Cross-Couplings: Emerging Approaches Towards Sustainability. Curr. Org. Synth., 2011, 8, 53-78.
[http://dx.doi.org/10.2174/157017911794407683]

(a) Appl, M. Ammonia: Principles and Industrial Practice; Wiley-VCH: Weinheim, Germany, 1999.
[http://dx.doi.org/10.1002/9783527613885]
(b)Appl, M. Ammonia.Ullmann’s Encyclopedia of Industrial Chemistry; Wiley-VCH: Weinheim, Germany, 2006.
[http://dx.doi.org/10.1002/14356007.a02_143.pub2]
(c)Enthaler, S. Ammonia: an environmentally friendly nitrogen source for primary aniline synthesis. ChemSusChem, 2010, 3(9), 1024-1029.
[http://dx.doi.org/10.1002/cssc.201000145] [PMID: 20572289]
(d)Roundhill, D.M. Transition metal and enzyme catalyzed reactions involving reactions with ammonia and amines. Chem. Rev., 1992, 92, 1-27.
[http://dx.doi.org/10.1021/cr00009a001]

(a) Surry, D.S.; Buchwald, S.L. Selective palladium-catalyzed arylation of ammonia: synthesis of anilines as well as symmetrical and unsymmetrical di- and triarylamines. J. Am. Chem. Soc., 2007, 129(34), 10354-10355.
[http://dx.doi.org/10.1021/ja074681a] [PMID: 17672469]
(b)Schulz, T.; Torborg, C.; Enthaler, S.; Schäffner, B.; Dumrath, A.; Spannenberg, A.; Neumann, H.; Börner, A.; Beller, M. A general palladium-catalyzed amination of aryl halides with ammonia. Chemistry, 2009, 15(18), 4528-4533.
[http://dx.doi.org/10.1002/chem.200802678] [PMID: 19322847]
(c)Wu, Z.; Jiang, Z.; Wu, D.; Xiang, H.; Zhou, X. A simple and efficient catalytic system for coupling aryl halides with aqueous ammonia in water. Eur. J. Org. Chem., 2010, 1854-1857.
[http://dx.doi.org/10.1002/ejoc.201000060]
(d)Jiang, L.; Lu, X.; Zhang, H.; Jiang, Y.; Ma, D. CuI/4-hydro-L-proline as a more effective catalytic system for coupling of aryl bromides with N-boc hydrazine and aqueous ammonia. J. Org. Chem., 2009, 74(12), 4542-4546.
[http://dx.doi.org/10.1021/jo9006738] [PMID: 19432437]

(a) Wolfe, J.P.; Ahman, J.; Sadighi, J.P.; Singer, R.A.; Buchwald, S.L. An ammonia equivalent for the palladium-catalyzed amination of aryl halides and triflates. Tetrahedron Lett., 1997, 38, 6367-6370.
[http://dx.doi.org/10.1016/S0040-4039(97)01465-2]
(b)Wolfe, J.P.; Tomori, H.; Sadighi, J.P.; Yin, J.; Buchwald, S.L. Simple, efficient catalyst system for the palladium-catalyzed amination of aryl chlorides, bromides, and triflates. J. Org. Chem., 2000, 65(4), 1158-1174.
[http://dx.doi.org/10.1021/jo991699y] [PMID: 10814067]
(c)Huang, X.; Buchwald, S.L. New ammonia equivalents for the Pd-catalyzed amination of aryl halides. Org. Lett., 2001, 3(21), 3417-3419.
[http://dx.doi.org/10.1021/ol0166808] [PMID: 11594848]
(d)Huang, X.; Anderson, K.W.; Zim, D.; Jiang, L.; Klapars, A.; Buchwald, S.L. Expanding Pd-catalyzed C-N bond-forming processes: the first amidation of aryl sulfonates, aqueous amination, and complementarity with Cu-catalyzed reactions. J. Am. Chem. Soc., 2003, 125(22), 6653-6655.
[http://dx.doi.org/10.1021/ja035483w] [PMID: 12769573]
(e)Lee, S.; Jørgensen, M.; Hartwig, J.F. Palladium-catalyzed synthesis of arylamines from aryl halides and lithium bis(trimethylsilyl)amide as an ammonia equivalent. Org. Lett., 2001, 3(17), 2729-2732.
[http://dx.doi.org/10.1021/ol016333y] [PMID: 11506620]
(f)Lee, D.Y.; Hartwig, J.F. Zinc trimethylsilylamide as a mild ammonia equivalent and base for the amination of aryl halides and triflates. Org. Lett., 2005, 7(6), 1169-1172.
[http://dx.doi.org/10.1021/ol050141b] [PMID: 15760166]

Ji, P.; Atherton, J.H.; Page, M.I. Copper(I)-catalyzed amination of aryl halides in liquid ammonia. J. Org. Chem., 2012, 77(17), 7471-7478.
[http://dx.doi.org/10.1021/jo301204t] [PMID: 22849292]

(a) Lu, Z.; Twieg, R.J. Copper-catalyzed aryl amination in aqueous media with 2-dimethylaminoethanol ligand. Tetrahedron Lett., 2005, 46, 2997-3001.
(b)Xu, H.; Wolf, C. Copper catalyzed coupling of aryl chlorides, bromides and iodides with amines and amides. J. Chem. Soc. Chem. Commun., 2009, 1715-1717.
(c)Kim, J.; Chang, S. Ammonium salts as an inexpensive and convenient nitrogen source in the Cu-catalyzed amination of aryl halides at room temperature. J. Chem. Soc. Chem. Commun., 2008, 3052-3054.
(d)Cortes-Salva, M.; Nguyen, B.; Cuevas, J.; Pennypacker, K.R.; Antilla, J.C. Copper-Catalyzed Guanidinylation of Aryl Iodides: The Formation of N,N′-Disubstituted Guanidines. Org. Lett., 2010, 12, 1316-1319.
(e)Surry, D.S.; Buchwald, S.L. Diamine ligands in copper-catalyzed reactions. Chem. Sci., 2010, 1, 13-31.
(f)Rout, L.; Jammi, S.; Punniyamurthy, T. Novel CuO nanoparticle catalyzed C− N cross coupling of amines with iodobenzene. Org. Lett., 2007, 9, 3397-3399.
(g)Lang, F.; Zewge, D.; Houpis, I.N.; Volante, R.P. Amination of aryl halides using copper catalysis. Tetrahedron Lett., 2001, 42, 3251-3254.

Wang, D.; Cai, Q.; Ding, K. An Efficient Copper-Catalyzed Amination of Aryl Halides by Aqueous Ammonia. Adv. Synth. Catal., 2009, 351, 1722-1726.
[http://dx.doi.org/10.1002/adsc.200900327]

Imada, Y.; Kitagawa, T.; Wang, H-K.; Komiya, N.; Naota, T. Flavin-catalyzed aerobic oxidation of sulfides in aqueous media. Tetrahedron Lett., 2013, 54, 621-624.
[http://dx.doi.org/10.1016/j.tetlet.2012.11.133]

(a) Imada, Y.; Naota, T. Flavins as organocatalysts for environmentally benign molecular transformations. Chem. Rec., 2007, 7(6), 354-361.
[http://dx.doi.org/10.1002/tcr.20135] [PMID: 18069686]
(b)Imada, Y.; Iida, H.; Murahashi, S.; Naota, T. An aerobic, organocatalytic, and chemoselective method for Baeyer-Villiger oxidation. Angew. Chem. Int. Ed. Engl., 2005, 44(11), 1704-1706.
[http://dx.doi.org/10.1002/anie.200462429] [PMID: 15693045]
(c)Imada, Y.; Iida, H.; Naota, T. Flavin-catalyzed generation of diimide: an environmentally friendly method for the aerobic hydrogenation of olefins. J. Am. Chem. Soc., 2005, 127(42), 14544-14545.
[http://dx.doi.org/10.1021/ja053976q] [PMID: 16231886]
(d)Imada, Y.; Kitagawa, T.; Ohno, T.; Iida, H.; Naota, T. Neutral flavins: green and robust organocatalysts for aerobic hydrogenation of olefins. Org. Lett., 2010, 12(1), 32-35.
[http://dx.doi.org/10.1021/ol902393p] [PMID: 19950976]
(e)Imada, Y.; Iida, H.; Kitagawa, T.; Naota, T. Aerobic reduction of olefins by in situ generation of diimide with synthetic flavin catalysts. Chemistry, 2011, 17(21), 5908-5920.
[http://dx.doi.org/10.1002/chem.201003278] [PMID: 21495097]
(f)Murahashi, S-I.; Oda, T.; Masui, Y. Flavin-catalyzed oxidation of amines and sulfur compounds with hydrogen peroxide. J. Am. Chem. Soc., 1989, 111, 5002-5003.
[http://dx.doi.org/10.1021/ja00195a076]
(g)Murahashi, S.; Ono, S.; Imada, Y. Asymmetric baeyer-villiger reaction with hydrogen peroxide catalyzed by a novel planar-chiral bisflavin. Angew. Chem. Int. Ed. Engl., 2002, 41(13), 2366-2368.
[http://dx.doi.org/10.1002/1521-3773(20020703)41:13<2366:AID-ANIE2366>3.0.CO;2-S] [PMID: 12203594]
(h)Imada, Y.; Ohno, T.; Naota, T. Oxidation of sulfides with hydrogen peroxide catalyzed by 10, 10′-linked bisflavinium perchlorates. Tetrahedron Lett., 2007, 48, 937-939.
[http://dx.doi.org/10.1016/j.tetlet.2006.12.017]

(a) Imada, Y.; Iida, H.; Ono, S.; Murahashi, S. Flavin catalyzed oxidations of sulfides and amines with molecular oxygen. J. Am. Chem. Soc., 2003, 125(10), 2868-2869.
[http://dx.doi.org/10.1021/ja028276p] [PMID: 12617641]
(b)Imada, Y.; Iida, H.; Ono, S.; Masui, Y.; Murahashi, S. Flavin-catalyzed oxidation of amines and sulfides with molecular oxygen: biomimetic green oxidation. Chem. Asian J., 2006, 1(1-2), 136-147.
[http://dx.doi.org/10.1002/asia.200600080] [PMID: 17441048]

(a) Mansuy, D.; Fontecave, M.; Bartoli, J-F. Mono-oxigenase-like dioxygen activation leading to alkane hydroxylation and olefin epoxidation by an Mn III (porphyrin)–ascorbate biphasic system. J. Chem. Soc. Chem. Commun., 1983, 6, 253-254.
[http://dx.doi.org/10.1039/C39830000253]
(b)Aihara, K.; Urano, Y.; Higuchi, T.; Hirobe, M. Mechanistic studies of selective catechol formation from o-methoxyphenols using a copper (II)–ascorbic acid–dioxygen system. J. Chem. Soc. Perkin Trans., 1993, 2, 2165-2170.
[http://dx.doi.org/10.1039/P29930002165]
(c)Shul’pin, G.B.; Lachter, E.R. Aerobic hydroxylation of hydrocarbons catalysed by vanadate ion. J. Mol. Catal. Chem., 2003, 197, 65-71.
[http://dx.doi.org/10.1016/S1381-1169(02)00677-5]

(a) Hassan, J.; Sévignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Aryl-aryl bond formation one century after the discovery of the Ullmann reaction. Chem. Rev., 2002, 102(5), 1359-1470.
[http://dx.doi.org/10.1021/cr000664r] [PMID: 11996540]
(b)Corbet, J-P.; Mignani, G. Selected patented cross-coupling reaction technologies. Chem. Rev., 2006, 106(7), 2651-2710.
[http://dx.doi.org/10.1021/cr0505268] [PMID: 16836296]

(a) Alberico, D.; Scott, M.E.; Lautens, M. Aryl-aryl bond formation by transition-metal-catalyzed direct arylation. Chem. Rev., 2007, 107(1), 174-238.
[http://dx.doi.org/10.1021/cr0509760] [PMID: 17212475]
(b)Lyons, T.W.; Sanford, M.S. Palladium-catalyzed ligand-directed C-H functionalization reactions. Chem. Rev., 2010, 110(2), 1147-1169.
[http://dx.doi.org/10.1021/cr900184e] [PMID: 20078038]
(c)Wencel-Delord, J.; Glorius, F. C-H bond activation enables the rapid construction and late-stage diversification of functional molecules. Nat. Chem., 2013, 5(5), 369-375.
[http://dx.doi.org/10.1038/nchem.1607] [PMID: 23609086]
(d)McGlacken, G.P.; Bateman, L.M. Recent advances in aryl-aryl bond formation by direct arylation. Chem. Soc. Rev., 2009, 38(8), 2447-2464.
[http://dx.doi.org/10.1039/b805701j] [PMID: 19623360]
(e)Anastas, P.; Eghbali, N. Green chemistry: principles and practice. Chem. Soc. Rev., 2010, 39(1), 301-312.
[http://dx.doi.org/10.1039/B918763B] [PMID: 20023854]
(f)Mehta, V.P.; Punji, B. Recent advances in transition-metal-free direct C–C and C–heteroatom bond forming reactions. RSC Advances, 2013, 3, 11957-11986.
[http://dx.doi.org/10.1039/c3ra40813b]
(g)Sun, C.L.; Li, H.; Yu, D.G.; Yu, M.; Zhou, X.; Lu, X.Y.; Huang, K.; Zheng, S.F.; Li, B.J.; Shi, Z.J. An efficient organocatalytic method for constructing biaryls through aromatic C-H activation. Nat. Chem., 2010, 2(12), 1044-1049.
[http://dx.doi.org/10.1038/nchem.862] [PMID: 21107368]
(h)Shirakawa, E.; Itoh, K.; Higashino, T.; Hayashi, T. tert-Butoxide-mediated arylation of benzene with aryl halides in the presence of a catalytic 1,10-phenanthroline derivative. J. Am. Chem. Soc., 2010, 132(44), 15537-15539.
[http://dx.doi.org/10.1021/ja1080822] [PMID: 20961045]
(i)Liu, W.; Cao, H.; Zhang, H.; Zhang, H.; Chung, K.H.; He, C.; Wang, H.; Kwong, F.Y.; Lei, A. Organocatalysis in cross-coupling: DMEDA-catalyzed direct C-H arylation of unactivated benzene. J. Am. Chem. Soc., 2010, 132(47), 16737-16740.
[http://dx.doi.org/10.1021/ja103050x] [PMID: 20677824]

Crisóstomo, F.P.; Martín, T.; Carrillo, R. Ascorbic acid as an initiator for the direct C-H arylation of (hetero)arenes with anilines nitrosated in situ. Angew. Chem. Int. Ed. Engl., 2014, 53(8), 2181-2185.
[http://dx.doi.org/10.1002/anie.201309761] [PMID: 24453180]

(a) Mo, F.; Jiang, Y.; Qiu, D.; Zhang, Y.; Wang, J. Direct conversion of arylamines to pinacol boronates: a metal-free borylation process. Angew. Chem. Int. Ed. Engl., 2010, 49(10), 1846-1849.
[http://dx.doi.org/10.1002/anie.200905824] [PMID: 20127778]
(b)Qiu, D.; Meng, H.; Jin, L.; Wang, S.; Tang, S.; Wang, X.; Mo, F.; Zhang, Y.; Wang, J. Synthesis of aryl trimethylstannanes from aryl amines: a Sandmeyer-type stannylation reaction. Angew. Chem. Int. Ed. Engl., 2013, 52(44), 11581-11584.
[http://dx.doi.org/10.1002/anie.201304579] [PMID: 24014092]
(c)Qiu, D.; Jin, L.; Zheng, Z.; Meng, H.; Mo, F.; Wang, X.; Zhang, Y.; Wang, J. Synthesis of pinacol arylboronates from aromatic amines: a metal-free transformation. J. Org. Chem., 2013, 78(5), 1923-1933.
[http://dx.doi.org/10.1021/jo3018878] [PMID: 23106090]

(a) Costas-Costas, U.; Gonzalez-Romero, E.; Bravo-Diaz, C. Effects of ascorbic acid on arenediazonium salts reactivity: kinetics and mechanism of the reaction. Helv. Chim. Acta, 2001, 84, 632-648.
[http://dx.doi.org/10.1002/1522-2675(20010321)84:3<632:AID-HLCA632>3.0.CO;2-0]
(b)Reszka, K.J.; Chignell, C.F. One-electron reduction of arenediazonium compounds by physiological electron donors generates aryl radicals. An EPR and spin trapping investigation. Chem. Biol. Interact., 1995, 96(3), 223-234.
[http://dx.doi.org/10.1016/0009-2797(94)03593-W] [PMID: 7750162]

Giese, B.; Kopping, B.; Gobel, T.; Dickhaut, J.; Thoma, G.; Kulicke, K.J. Trach., F. Radical cyclization reactions. Org. React., 1996, 48, 301-361.

Liu, S.; Cheng, P.; Liu, W.; Zeng, J.G. Ascorbic Acid-Initiated Tandem Radical Cyclization of N-Arylacrylamides to Give 3,3-Disubstituted Oxindoles. Molecules, 2015, 20(9), 15631-15642.
[http://dx.doi.org/10.3390/molecules200915631] [PMID: 26343622]

(a) Parry, R.J. Biosynthesis of some sulfur-containing natural products investigations of the mechanism of carbon-sulfur bond formation. Tetrahedron, 1983, 39, 1215-1238.
[http://dx.doi.org/10.1016/S0040-4020(01)91887-3]
(b)Jacob, C. A scent of therapy: pharmacological implications of natural products containing redox-active sulfur atoms. Nat. Prod. Rep., 2006, 23(6), 851-863.
[http://dx.doi.org/10.1039/b609523m] [PMID: 17119635]
(c)Fontecave, M.; Ollagnier-de-Choudens, S.; Mulliez, E. Biological radical sulfur insertion reactions. Chem. Rev., 2003, 103(6), 2149-2166.
[http://dx.doi.org/10.1021/cr020427j] [PMID: 12797827]
(d)Procter, D.J. The synthesis of thiols, selenols, sulfides, selenides, sulfoxides, selenoxides, sulfones and selenones. J. Chem. Soc. Perkin Trans., 2001, 1, 335-354.
[http://dx.doi.org/10.1039/b002081h]
(e)Rayner, C.M. Synthesis of thiols, selenols, sulfides, selenides, sulfoxides, selenoxides, sulfones and selenones. Contemp. Org. Synth., 1996, 3, 499-533.
[http://dx.doi.org/10.1039/co9960300499]
(f)Hoyle, C.E.; Lee, T.Y.; Roper, T. J. Polym. Sci., Part A: Thiol–enes: Chemistry of the past with promise for the future. Polym. Chem., 2004, 42, 5301-5338.
[http://dx.doi.org/10.1002/pola.20366]
(g)Clemenson, P.I. The chemistry and solid state properties of nickel, palladium and platinum bis (maleonitriledithiolate) compounds. Coord. Chem. Rev., 1990, 106, 171-203.
[http://dx.doi.org/10.1016/0010-8545(60)80003-3]

(a) McGarrigle, E.M.; Myers, E.L.; Illa, O.; Shaw, M.A.; Riches, S.L.; Aggarwal, V.K. Chalcogenides as organocatalysts. Chem. Rev., 2007, 107(12), 5841-5883.
[http://dx.doi.org/10.1021/cr068402y] [PMID: 18072810]
(b)Gómez Arrayás, R.; Carretero, J.C. Chiral thioether-based catalysts in asymmetric synthesis: recent advances. Chem. Commun. (Camb.), 2011, 47(8), 2207-2211.
[http://dx.doi.org/10.1039/C0CC03978K] [PMID: 21127802]

(a) Beletskaya, I.P.; Ananikov, V.P. Transition-metal-catalyzed C-S, C-Se, and C-Te bond formation via cross-coupling and atom-economic addition reactions. Chem. Rev., 2011, 111(3), 1596-1636.
[http://dx.doi.org/10.1021/cr100347k] [PMID: 21391564]
(b)Kondo, T.; Mitsudo Ta, T.A. Metal-catalyzed carbon-sulfur bond formation. Chem. Rev., 2000, 100(8), 3205-3220.
[http://dx.doi.org/10.1021/cr9902749] [PMID: 11749318]
(c)Hoyle, C.E.; Lowe, A.B.; Bowman, C.N. Thiol-click chemistry: a multifaceted toolbox for small molecule and polymer synthesis. Chem. Soc. Rev., 2010, 39(4), 1355-1387.
[http://dx.doi.org/10.1039/b901979k] [PMID: 20309491]
(d)Chauhan, P.; Mahajan, S.; Enders, D. Organocatalytic carbon-sulfur bond-forming reactions. Chem. Rev., 2014, 114(18), 8807-8864.
[http://dx.doi.org/10.1021/cr500235v] [PMID: 25144663]
(e)Ley, S.V.; Thomas, A.W. Modern synthetic methods for copper-mediated C(aryl)[bond]O, C(aryl)[bond]N, and C(aryl)[bond]S bond formation. Angew. Chem. Int. Ed. Engl., 2003, 42(44), 5400-5449.
[http://dx.doi.org/10.1002/anie.200300594] [PMID: 14618572]

(a) Eichman, C.C.; Stambuli, J.P. Transition metal catalyzed synthesis of aryl sulfides. Molecules, 2011, 16(1), 590-608.
[http://dx.doi.org/10.3390/molecules16010590] [PMID: 21242940]
(b)Baig, R.B.N.; Varma, R.S. A highly active and magnetically retrievable nanoferrite-DOPA-copper catalyst for the coupling of thiophenols with aryl halides. Chem. Commun. (Camb.), 2012, 48(20), 2582-2584.
[http://dx.doi.org/10.1039/c2cc17283f] [PMID: 22293995]
(c)Wu, Q.; Zhao, D.; Qin, X.; Lan, J.; You, J. Synthesis of di(hetero)aryl sulfides by directly using arylsulfonyl chlorides as a sulfur source. Chem. Commun. (Camb.), 2011, 47(32), 9188-9190.
[http://dx.doi.org/10.1039/c1cc13633j] [PMID: 21750836]
(d)Kundu, D.; Ahammed, S.; Ranu, B.C. Microwave-assisted reaction of aryl diazonium fluoroborate and diaryl dichalcogenides in dimethyl carbonate: a general procedure for the synthesis of unsymmetrical diaryl chalcogenides. Green Chem., 2012, 14, 2024-2030.
[http://dx.doi.org/10.1039/c2gc35328h]
(e)Cheng, J-H.; Ramesh, C.; Kao, H-L.; Wang, Y-J.; Chan, C-C.; Lee, C.F. Synthesis of aryl thioethers through the N-chlorosuccinimide-promoted cross-coupling reaction of thiols with Grignard reagents. J. Org. Chem., 2012, 77(22), 10369-10374.
[http://dx.doi.org/10.1021/jo302088t] [PMID: 23067042]

(a) Stadler, O. Zur Kenntniss der Merkaptane. Ber. Dtsch. Chem. Ges., 1884, 17, 2075-2081.
[http://dx.doi.org/10.1002/cber.188401702106]
(b)Ziegler, J.H. Ueber eine Methode zur Darstellung aromatischer Sulfide von bestimmter Constitution und das Thioxanthon. Ber. Dtsch. Chem. Ges., 1890, 23, 2469.
[http://dx.doi.org/10.1002/cber.189002302128]

(a) Hilbert, G.E.; Johnson, T.B. A study of the germicidal activity of diaryl-sulfide phenols. J. Am. Chem. Soc., 1929, 51, 1526-1536.
[http://dx.doi.org/10.1021/ja01380a033]
(b)Szmant, H.H.; Levitt, G. p-Nitrophenyl p-Acylphenyl Sulfides and Related Compounds. J. Am. Chem. Soc., 1954, 76, 5459-5461.
[http://dx.doi.org/10.1021/ja01650a059]
(c)Baleja, J.D. The Facile Conversion of Aromatic Amines to Arylmethylsulfides with Methylthiocopper. Synth. Commun., 1984, 14, 215-218.
[http://dx.doi.org/10.1080/00397918408060724]
(d)Petrillo, G.; Novi, M.; Garbarino, G.; Dell’Erba, C. A simple preparation of symmetrical and unsymmetrical diarylsulfides from arenediazonium tetrafluoroborates. Tetrahedron Lett., 1985, 26, 6365-6368.
[http://dx.doi.org/10.1016/S0040-4039(01)84600-1]

Wang, X.; Cuny, G.D.; Noël, T. A mild, one-pot Stadler-Ziegler synthesis of arylsulfides facilitated by photoredox catalysis in batch and continuous-flow. Angew. Chem. Int. Ed. Engl., 2013, 52(30), 7860-7864.
[http://dx.doi.org/10.1002/anie.201303483] [PMID: 23784666]

(a) Hartwig, J.F. Evolution of a fourth generation catalyst for the amination and thioetherification of aryl halides. Acc. Chem. Res., 2008, 41(11), 1534-1544.
[http://dx.doi.org/10.1021/ar800098p] [PMID: 18681463]
(b)Carril, M.; SanMartin, R.; Domínguez, E. Palladium and copper-catalysed arylation reactions in the presence of water, with a focus on carbon-heteroatom bond formation. Chem. Soc. Rev., 2008, 37(4), 639-647.
[http://dx.doi.org/10.1039/b709565c] [PMID: 18362973]
(c)Beletskaya, I.P.; Cheprakov, A.V. Copper in cross-coupling reactions: The post-Ullmann chemistry. Coord. Chem. Rev., 2004, 248, 2337-2364.
[http://dx.doi.org/10.1016/j.ccr.2004.09.014]
(d)Prim, D.; Campagne, J-M.; Joseph, D.; Andrioletti, B. Palladium-catalysed reactions of aryl halides with soft, non-organometallic nucleophiles. Tetrahedron, 2002, 58, 2041-2075.
[http://dx.doi.org/10.1016/S0040-4020(02)00076-5]
(e)Kunz, K.; Scholz, U.; Ganzer, D. Renaissance of Ullmann and Goldberg Reactions - Progress in Copper Catalyzed C-N-, C-O- and C-S-Coupling. Synlett, 2003, 15, 2428-2439.
[http://dx.doi.org/10.1055/s-2003-42473]
(f)Alvaro, E.; Hartwig, J.F. Resting state and elementary steps of the coupling of aryl halides with thiols catalyzed by alkylbisphosphine complexes of palladium. J. Am. Chem. Soc., 2009, 131(22), 7858-7868.
[http://dx.doi.org/10.1021/ja901793w] [PMID: 19453106]
(g)Fernández-Rodríguez, M.A.; Shen, Q.; Hartwig, J.F. Highly efficient and functional-group-tolerant catalysts for the palladium-catalyzed coupling of aryl chlorides with thiols. Chemistry, 2006, 12(30), 7782-7796.
[http://dx.doi.org/10.1002/chem.200600949] [PMID: 17009367]
(h)Fukuzawa, S-i.; Tanihara, D.; Kikuchi, S. Palladium-catalyzed coupling reaction of diaryl dichalcogenide with aryl bromide leading to the synthesis of unsymmetrical aryl chalcogenide. Synlett, 2006, 13, 2145-2147.
[http://dx.doi.org/10.1055/s-2006-949607]
(i)Bhadra, S.; Sreedhar, B.; Ranu, B.C. Recyclable heterogeneous supported copper‐catalyzed coupling of thiols with aryl halides: base‐controlled differential arylthiolation of bromoiodobenzenes. Adv. Synth. Catal., 2009, 351, 2369-2378.
[http://dx.doi.org/10.1002/adsc.200900358]
(j)Zhang, Y.; Ngeow, K.C.; Ying, J.Y. The first N-heterocyclic carbene-based nickel catalyst for C-S coupling. Org. Lett., 2007, 9(18), 3495-3498.
[http://dx.doi.org/10.1021/ol071248x] [PMID: 17676857]

(a) Majek, M.; von Wangelin, A.J. Organocatalytic visible light mediated synthesis of aryl sulfides. Chem. Commun. (Camb.), 2013, 49(48), 5507-5509.
[http://dx.doi.org/10.1039/c3cc41867g] [PMID: 23660726]
(b)Du, B.; Jin, B.; Sun, P. Syntheses of sulfides and selenides through direct oxidative functionalization of C(sp3)-H bond. Org. Lett., 2014, 16(11), 3032-3035.
[http://dx.doi.org/10.1021/ol5011449] [PMID: 24835082]
(c)Guo, S.R.; Yuan, Y.Q.; Xiang, J.N. Metal-free oxidative C(sp3)-H bond thiolation of ethers with disulfides. Org. Lett., 2013, 15(18), 4654-4657.
[http://dx.doi.org/10.1021/ol402281f] [PMID: 23987104]
(d)Wang, P.F.; Wang, X.Q.; Dai, J.J.; Feng, Y.S.; Xu, H.J. Silver-mediated decarboxylative C-S cross-coupling of aliphatic carboxylic acids under mild conditions. Org. Lett., 2014, 16(17), 4586-4589.
[http://dx.doi.org/10.1021/ol502144c] [PMID: 25153507]

Bu, M.j.; Lu, G-p.; Cai, C. Ascorbic Acid Promoted Metal-Free Synthesis of Aryl Sulfides with Anilines Nitrosated in Situ by tert-Butyl Nitrite. Synlett, 2015, 26, 1841-1846.
[http://dx.doi.org/10.1055/s-0034-1378738]

(a) Lian, M.; Li, Q.; Zhu, Y.; Yin, G.; Wu, A. Logic design and synthesis of quinoxalines via the integration of iodination/oxidation/cyclization sequences from ketones and 1, 2-diamines. Tetrahedron, 2012, 68, 9598-9605.
[http://dx.doi.org/10.1016/j.tet.2012.09.056]
(b)Cho, C.S.; Ren, W.X.; Shim, S.C. Ketones as a new synthon for quinoxaline synthesis. Tetrahedron Lett., 2007, 48, 4665-4667.
[http://dx.doi.org/10.1016/j.tetlet.2007.05.044]
(c)Qi, C.; Jiang, H.; Huang, L.; Chen, Z.; Chen, H. DABCO-catalyzed oxidation of deoxybenzoins to benzils with air and one-pot synthesis of quinoxalines. Synthesis, 2011, 3, 387-396.

(a) Yang, Y.; Yao, J.; Zhang, Y. Synthesis of polysubstituted furans via copper-mediated annulation of alkyl ketones with α,β-unsaturated carboxylic acids. Org. Lett., 2013, 15(13), 3206-3209.
[http://dx.doi.org/10.1021/ol400912v] [PMID: 23772562]
(b)Naveen, T.; Kancherla, R.; Maiti, D. Radical based strategy toward the synthesis of 2,3-dihydrofurans from aryl ketones and aromatic olefins. Org. Lett., 2014, 16(20), 5446-5449.
[http://dx.doi.org/10.1021/ol502688r] [PMID: 25275799]

Huang, H.; Ji, X.; Wu, W.; Jiang, H. Practical Synthesis of Polysubstituted Imidazoles via Iodine-Catalyzed Aerobic Oxidative Cyclization of Aryl Ketones and Benzylamines. Adv. Synth. Catal., 2013, 355, 170-180.
[http://dx.doi.org/10.1002/adsc.201200582]

(a) Hon, Y-S.; Hsu, T-R.; Chen, C-Y.; Lin, Y-H.; Chang, F-J.; Hsieh, C-H.; Szu, P-H. Dibromomethane as one-carbon source in organic synthesis: microwave-accelerated α-methylenation of ketones with dibromomethane and diethylamine. Tetrahedron, 2003, 59, 1509-1520.
[http://dx.doi.org/10.1016/S0040-4020(03)00080-2]
(b)Liu, J.; Yi, H.; Zhang, X.; Liu, C.; Liu, R.; Zhang, G.; Lei, A. Copper-catalysed oxidative Csp(3)-H methylenation to terminal olefins using DMF. Chem. Commun. (Camb.), 2014, 50(57), 7636-7638.
[http://dx.doi.org/10.1039/C4CC02275K] [PMID: 24893656]

(a) Stavber, G.; Iskara, J.; Zupan, M.; Stavber, S. Aerobic oxidative iodination of ketones catalysed by sodium nitrite “on water” or in a micelle-based aqueous system. Green Chem., 2009, 11, 1262-1267.
[http://dx.doi.org/10.1039/b902230a]
(b)Liang, Y-F.; Wu, K.; Song, S.; Li, X.; Huang, X.; Jiao, N. I2- or NBS-catalyzed highly efficient α-hydroxylation of ketones with dimethyl sulfoxide. Org. Lett., 2015, 17(4), 876-879.
[http://dx.doi.org/10.1021/ol5037387] [PMID: 25650782]

(a) Lee, J.C.; Park, H-J.; Park, J.Y. Rapid microwave-promoted solvent-free oxidation of α-methylene ketones to α-diketones. Tetrahedron Lett., 2002, 43, 5661-5663.
[http://dx.doi.org/10.1016/S0040-4039(02)01130-9]
(b)Urgoitia, G.; SanMartin, R.; Herrero, M.T.; Dominguer, E. Palladium NCN and CNC pincer complexes as exceptionally active catalysts for aerobic oxidation in sustainable media. Green Chem., 2011, 13, 2161-2166.
[http://dx.doi.org/10.1039/c1gc15390k]
(c)Cacchi, S.; Fabrizi, G.; Goggiamani, A. IAZZetti, A.; Verdiglione, R. Copper-Catalyzed oxidation of deoxybenzoins to benzils under aerobic conditions. Synthesis, 2013, 45, 1701-1707.
[http://dx.doi.org/10.1055/s-0033-1338451]

Maji, A.; Rana, S. Akanksha; Maiti, D. Synthesis of bis(heteroaryl) ketones by removal of benzylic CHR and CO groups. Angew. Chem. Int. Ed. Engl., 2014, 53(9), 2428-2432.
[http://dx.doi.org/10.1002/anie.201308785] [PMID: 24481978]

(a) Churruca, F.; Sanmartin, R.; Tellitu, I.; Dominguez, E. PCP-Bis (phosphinite) pincer complexes: new homogeneous catalysts for α-arylation of ketones. Tetrahedron Lett., 2006, 47, 3233-3237.
[http://dx.doi.org/10.1016/j.tetlet.2006.03.040]
(b)Churruca, F.; SanMartin, R.; Tellitu, I.; Domínguez, E. Palladium-catalyzed arylation of ketone enolates: an expeditious entry to tamoxifen-related 1,2,2-triarylethanones. Org. Lett., 2002, 4(9), 1591-1594.
[http://dx.doi.org/10.1021/ol025811h] [PMID: 11975636]

Bu, M.; Niu, T.F.; Cai, C. Visible-light-mediated oxidative arylation of vinylarenes under aerobic conditions. Catal. Sci. Technol., 2015, 5, 830-834.
[http://dx.doi.org/10.1039/C4CY01523A]

Majhi, B.; Kundu, D.; Ranu, B.C. Ascorbic acid promoted oxidative arylation of vinyl arenes to 2-aryl acetophenones without irradiation at room temperature under aerobic conditions. J. Org. Chem., 2015, 80(15), 7739-7745.
[http://dx.doi.org/10.1021/acs.joc.5b00825] [PMID: 26154891]

(a) Tucker, J.W.; Narayanam, J.M.R.; Shah, P.S.; Stephenson, C.R. Oxidative photoredox catalysis: mild and selective deprotection of PMB ethers mediated by visible light. Chem. Commun. (Camb.), 2011, 47(17), 5040-5042.
[http://dx.doi.org/10.1039/c1cc10827a] [PMID: 21431223]
(b)Giedyk, M.; Turkowska, J.; Lepak, S.; Marculewicz, M.; Ó Proinsias, K.; Gryko, D. Photoinduced Vitamin B12-Catalysis for Deprotection of (Allyloxy)arenes. Org. Lett., 2017, 19(10), 2670-2673.
[http://dx.doi.org/10.1021/acs.orglett.7b01012] [PMID: 28453294]
(c)DeClue, M.S.; Monnard, P-A.; Bailey, J.A.; Maurer, S.E.; Collis, G.E.; Ziock, H-J.; Rasmussen, S.; Boncella, J.M. Nucleobase mediated, photocatalytic vesicle formation from an ester precursor. J. Am. Chem. Soc., 2009, 131(3), 931-933.
[http://dx.doi.org/10.1021/ja808200n] [PMID: 19115944]
(d)Borak, J.B.; Lee, H-Y.; Raghavan, S.R.; Falvey, D.E. Application of PET deprotection for orthogonal photocontrol of aqueous solution viscosity. Chem. Commun. (Camb.), 2010, 46(47), 8983-8985.
[http://dx.doi.org/10.1039/c0cc02203a] [PMID: 20967368]
(e)Borak, J.B.; Falvey, D.E. A new photolabile protecting group for release of carboxylic acids by visible-light-induced direct and mediated electron transfer. J. Org. Chem., 2009, 74(10), 3894-3899.
[http://dx.doi.org/10.1021/jo900182x] [PMID: 19361187]
(f)Falvey, D.E.; Sundararajan, C. Photoremovable protecting groups based on electron transfer chemistry. Photochem. Photobiol. Sci., 2004, 3(9), 831-838.
[http://dx.doi.org/10.1039/b406866a] [PMID: 15346183]
(g)Sundararajan, C.; Falvey, D.E. C-O bond fragmentation of 4-picolyl- and N-methyl-4-picolinium esters triggered by photochemical electron transfer. J. Org. Chem., 2004, 69(17), 5547-5554.
[http://dx.doi.org/10.1021/jo049501j] [PMID: 15307722]

Todorov, A.R.; Wirtanen, T.; Helaja, J. Photoreductive Removal of O-Benzyl Groups from Oxyarene N-Heterocycles Assisted by O-Pyridine-pyridone Tautomerism. J. Org. Chem., 2017, 82(24), 13756-13767.
[http://dx.doi.org/10.1021/acs.joc.7b02775] [PMID: 29135249]

Groenenboom, M.C.; Saravanan, K.; Zhu, Y.; Carr, J.M.; Marjolin, A.; Faura, G.G.; Yu, E.C.; Dominey, R.N.; Keith, J.A. Structural and substituent group effects on multielectron standard reduction potentials of aromatic N-Heterocycles. J. Phys. Chem. A, 2016, 120(34), 6888-6894.
[http://dx.doi.org/10.1021/acs.jpca.6b07291] [PMID: 27529793]

Prier, C.K.; Rankic, D.A.; MacMillan, D.W.C. Visible light photoredox catalysis with transition metal complexes: applications in organic synthesis. Chem. Rev., 2013, 113(7), 5322-5363.
[http://dx.doi.org/10.1021/cr300503r] [PMID: 23509883]

(a) Liang, T.; Neumann, C.N.; Ritter, T. Introduction of fluorine and fluorine-containing functional groups. Angew. Chem. Int. Ed. Engl., 2013, 52(32), 8214-8264.
[http://dx.doi.org/10.1002/anie.201206566] [PMID: 23873766]
(b)Campbell, M.G.; Ritter, T. Late-stage fluorination: from fundamentals to application. Org. Process Res. Dev., 2014, 18(4), 474-480.
[http://dx.doi.org/10.1021/op400349g] [PMID: 25838756]
(c)Kawamura, S.; Dosei, K.; Valverde, E.; Ushida, K.; Sodeoka, M. N-Heterocycle-Forming Amino/Carboperfluoroalkylations of Aminoalkenes by Using Perfluoro Acid Anhydrides: Mechanistic Studies and Applications Directed Toward Perfluoroalkylated Compound Libraries. J. Org. Chem., 2017, 82(23), 12539-12553.
[http://dx.doi.org/10.1021/acs.joc.7b02307] [PMID: 29052416]
(d)Wang, Y.; Wang, J.; Li, G-X.; He, G.; Chen, G. Halogen-bond-promoted photoactivation of perfluoroalkyl iodides: a photochemical protocol for perfluoroalkylation reactions. Org. Lett., 2017, 19(6), 1442-1445.
[http://dx.doi.org/10.1021/acs.orglett.7b00375] [PMID: 28263075]
(e)Huang, Y.; Ajitha, M.J.; Huang, K-W.; Zhang, Z.; Weng, Z. A class of effective decarboxylative perfluoroalkylating reagents: [(phen)2Cu](O2CRF). Dalton Trans., 2016, 45(20), 8468-8474.
[http://dx.doi.org/10.1039/C6DT00277C] [PMID: 27114043]
(f)Wu, C.; Huang, Y.; Zhang, Z.; Weng, Z. Decarboxylative Perfluoroalkylation of Vinyl Bromides with Copper (I). Perfluorocarboxylato Complexes. Asian J. Org. Chem., 2016, 5, 1406-1410.
[http://dx.doi.org/10.1002/ajoc.201600348]
(g)Chen, X.; Tan, Z.; Gui, Q.; Hu, L.; Liu, J.; Wu, J.; Wang, G. Photocatalytic/Cu-Promoted C-H Activations: Visible-light-Induced ortho-Selective Perfluoroalkylation of Benzamides. Chemistry, 2016, 22(18), 6218-6222.
[http://dx.doi.org/10.1002/chem.201600229] [PMID: 26933840]

(a) Wang, J.; Sánchez-Roselló, M.; Aceña, J.L.; del Pozo, C.; Sorochinsky, A.E.; Fustero, S.; Soloshonok, V.A.; Liu, H. Fluorine in pharmaceutical industry: fluorine-containing drugs introduced to the market in the last decade (2001-2011). Chem. Rev., 2014, 114(4), 2432-2506.
[http://dx.doi.org/10.1021/cr4002879] [PMID: 24299176]
(b)Hagmann, W.K. The many roles for fluorine in medicinal chemistry. J. Med. Chem., 2008, 51(15), 4359-4369.
[http://dx.doi.org/10.1021/jm800219f] [PMID: 18570365]
(c)Purser, S.; Moore, P.R.; Swallow, S.; Gouverneur, V. Fluorine in medicinal chemistry. Chem. Soc. Rev., 2008, 37(2), 320-330.
[http://dx.doi.org/10.1039/B610213C] [PMID: 18197348]

(a) Prakash, G.K.S.; Yudin, A.K. Perfluoroalkylation with organosilicon reagents. Chem. Rev., 1997, 97(3), 757-786.
[http://dx.doi.org/10.1021/cr9408991] [PMID: 11848888]
(b)Liu, X.; Xu, C.; Wang, M.; Liu, Q. Trifluoromethyltrimethylsilane: nucleophilic trifluoromethylation and beyond. Chem. Rev., 2015, 115(2), 683-730.
[http://dx.doi.org/10.1021/cr400473a] [PMID: 24754488]
(c)Krishnamoorthy, S.; Prakash, G.K.S. Silicon-based reagents for difluoromethylation and difluoromethylenation reactions. Synthesis, 2017, 49, 3394-3406.
[http://dx.doi.org/10.1055/s-0036-1588489]
(d)Dilman, A.D.; Levin, V.V. Synthesis of organofluorine compounds using α-fluorine-substituted silicon reagents. Mendeleev Commun., 2015, 25, 239-244.
[http://dx.doi.org/10.1016/j.mencom.2015.07.001]
(e)Prakash, G.K.S.; Zhang, Z. Modern Synthesis Processes and Reactivity of Fluorinated Compounds; Groult, H.; Leroux, F.R; Tressaud, A., Ed.; Elsevier: Amsterdam, 2017, pp. 289-337.
[http://dx.doi.org/10.1016/B978-0-12-803740-9.00011-1]

(a) Evans, C.A. Spin trapping. Aldrichim Acta, 1979, 12, 23-29.
(b)Berliner, L.J. Assessment of nitrones as in vivo redox sensors. Appl. Magn. Reson., 2009, 36, 157-170.
[http://dx.doi.org/10.1007/s00723-009-0034-2]

(a) Wang, Y.; Noble, A.; Sandford, C.; Aggarwal, V.K. Enantiospecific Trifluoromethyl-Radical-Induced Three-Component Coupling of Boronic Esters with Furans. Angew. Chem. Int. Ed. Engl., 2017, 56(7), 1810-1814.
[http://dx.doi.org/10.1002/anie.201611058] [PMID: 28097819]
(b)Klein, A.; Vicic, D.A.; Biewer, C.; Kieltsch, I.; Stirnat, K.; Hamacher, C. Oxidative Cleavage of CH3 and CF3 Radicals from BOXAM Nickel Complexes. Organometallics, 2012, 31, 5334-5341.
[http://dx.doi.org/10.1021/om300342r]

Supranovich, V.I.; Levin, V.V.; Struchkova, M.I.; Dilman, A.D. Photocatalytic Reductive Fluoroalkylation of Nitrones. Org. Lett., 2018, 20(3), 840-843.
[http://dx.doi.org/10.1021/acs.orglett.7b03987] [PMID: 29355326]

Wallentin, C-J.; Nguyen, J.D.; Finkbeiner, P.; Stephenson, C.R.J. Visible light-mediated atom transfer radical addition via oxidative and reductive quenching of photocatalysts. J. Am. Chem. Soc., 2012, 134(21), 8875-8884.
[http://dx.doi.org/10.1021/ja300798k] [PMID: 22486313]

(a) Warren, J.J.; Mayer, J.M. Surprisingly long-lived ascorbyl radicals in acetonitrile: concerted proton-electron transfer reactions and thermochemistry. J. Am. Chem. Soc., 2008, 130(24), 7546-7547.
[http://dx.doi.org/10.1021/ja802055t] [PMID: 18505256]
(b)Warren, J.J.; Mayer, J.M. Tuning of the thermochemical and kinetic properties of ascorbate by its local environment: solution chemistry and biochemical implications. J. Am. Chem. Soc., 2010, 132(22), 7784-7793.
[http://dx.doi.org/10.1021/ja102337n] [PMID: 20476757]

(a) Levin, V.V.; Zemtsov, A.A.; Struchkova, M.I.; Dilman, A.D. Reactions of difluorocarbene with organozinc reagents. Org. Lett., 2013, 15(4), 917-919.
[http://dx.doi.org/10.1021/ol400122k] [PMID: 23368906]
(b)Chernov, G.N.; Levin, V.V.; Kokorekin, V.A.; Struchkova, M.I.; Dilman, A.D. Interaction of gem-Difluorinated Iodides with Silyl Enol Ethers Mediated by Photoredox Catalysis. Adv. Synth. Catal., 2017, 359, 3063-3067.
[http://dx.doi.org/10.1002/adsc.201700423]

Sladojevich, F.; McNeill, E.; Börgel, J.; Zheng, S-L.; Ritter, T. Condensed-phase, halogen-bonded CF3I and C2F5I adducts for perfluoroalkylation reactions. Angew. Chem. Int. Ed. Engl., 2015, 54(12), 3712-3716.
[http://dx.doi.org/10.1002/anie.201410954] [PMID: 25651531]

Burk, S.D.; Danheiser, R.L., Eds.; Handbook of reagents for organic synthesis, oxidising and reducing agents; Wiley-VCH: New York, 1999.
Nitro compounds, aromatic.Booth, G In: Ed.; Ullmann’s Encyclopedia of Industrial Chemistry; Wiley-VCH: Weinheim, 2012.

(a) Rylander, P.N., Ed.; Hydrogenation methods; Academic Press: New York, 1985.
(b) Trost, B.M.; Fleming, I., Eds.; Comprehensive organic synthesis. Selectivity, strategy and efficiency in modern organic chemistry; Pergamon: Oxford, 1991.

Orlandi, M.; Brenna, D.; Harms, R.; Jost, S.; Benaglia, M. Recent developments in the reduction of aromatic and aliphatic nitro compounds to amines. Org. Process Res. Dev., 2018, 22, 430-445.
[http://dx.doi.org/10.1021/acs.oprd.6b00205]

Todorov, A.R.; Aikonen, S.; Muuronen, M.; Helaja, J. Visible-Light-Photocatalyzed Reductions of N-Heterocyclic Nitroaryls to Anilines Utilizing Ascorbic Acid Reductant. Org. Lett., 2019, 21(10), 3764-3768.
[http://dx.doi.org/10.1021/acs.orglett.9b01205] [PMID: 31066563]

(a) Edson, J.B.; Spencer, L.P.; Boncella, J.M. Photorelease of primary aliphatic and aromatic amines by visible-light-induced electron transfer. Org. Lett., 2011, 13(23), 6156-6159.
[http://dx.doi.org/10.1021/ol202456d] [PMID: 22046963]
(b)Binstead, R.A.; McGuire, M.E.; Dovletoglou, A.; Seok, W.K.; Roecker, L.E.; Meyer, T.J. Oxidation of hydroquinones by [(bpy)2(py)RuIV(0)]2+ and [(bpy)2(py)RuIII(OH)]2+. Proton-coupled electron transfer. J. Am. Chem. Soc., 1992, 114, 173-186.
[http://dx.doi.org/10.1021/ja00027a025]

Maji, T.; Karmakar, A.; Reiser, O. Visible-light photoredox catalysis: dehalogenation of vicinal dibromo-, α-halo-, and α,α-dibromocarbonyl compounds. J. Org. Chem., 2011, 76(2), 736-739.
[http://dx.doi.org/10.1021/jo102239x] [PMID: 21192632]

(a) Schä ffner, B.; Schä ffner, F.; Verevkin, S. P.; Bö rner, A. Organic carbonates as solvents in synthesis and catalysis. Chem. Rev., 2010, 110, 4554-4581.
[http://dx.doi.org/10.1021/cr900393d]
(b)Lawrenson, S.; North, M.; Peigneguy, F.; Routledge, A. Greener solvents for solid-phase synthesis. Green Chem., 2017, 19, 952-962.
[http://dx.doi.org/10.1039/C6GC03147A]
(c)Sathish, M.; Sreeram, K.J.; Raghava Rao, J.; Unni Nair, B. Cyclic Carbonate: A Recyclable Medium for Zero Discharge Tanning. ACS Sustain. Chem.& Eng., 2016, 4, 1032-1040.
[http://dx.doi.org/10.1021/acssuschemeng.5b01121]
(d)Han, Z.; Rong, L.; Wu, J.; Zhang, L.; Wang, Z.; Ding, K. Catalytic hydrogenation of cyclic carbonates: a practical approach from CO2 and epoxides to methanol and diols. Angew. Chem. Int. Ed. Engl., 2012, 51(52), 13041-13045.
[http://dx.doi.org/10.1002/anie.201207781] [PMID: 23161665]
(e)Fukuoka, S.; Kawamura, M.; Komiya, K.; Tojo, M.; Hachiya, H.; Hasegawa, K.; Aminaka, M.; Okamoto, H.; Fukawa, I.; Konno, S. A novel non-phosgene polycarbonate production process using by-product CO2 as starting material. Green Chem., 2003, 5, 497-507.
[http://dx.doi.org/10.1039/B304963A]
(f)Laserna, V.; Fiorani, G.; Whiteoak, C.J.; Martin, E.; Escudero-Adán, E.; Kleij, A.W. Carbon dioxide as a protecting group: highly efficient and selective catalytic access to cyclic cis-diol scaffolds. Angew. Chem. Int. Ed. Engl., 2014, 53(39), 10416-10419.
[http://dx.doi.org/10.1002/anie.201406645] [PMID: 25132290]
(g)Beattie, C.; North, M.; Villuendas, P.; Young, C. Influence of temperature and pressure on cyclic carbonate synthesis catalyzed by bimetallic aluminum complexes and application to overall syn-bis-hydroxylation of alkenes. J. Org. Chem., 2013, 78(2), 419-426.
[http://dx.doi.org/10.1021/jo302317w] [PMID: 23256882]
(h)Kim, S.H.; Hong, S.H. Transfer hydrogenation of organic formates and cyclic carbonates: an alternative route to methanol from carbon dioxide. ACS Catal., 2014, 4, 3630-3636.
[http://dx.doi.org/10.1021/cs501133m]
(i)Khan, A.; Yang, L.; Xu, J.; Jin, L.Y.; Zhang, Y.J. Palladium-catalyzed asymmetric decarboxylative cycloaddition of vinylethylene carbonates with Michael acceptors: construction of vicinal quaternary stereocenters. Angew. Chem. Int. Ed. Engl., 2014, 53(42), 11257-11260.
[http://dx.doi.org/10.1002/anie.201407013] [PMID: 25168969]
(j)Liu, H.; Huang, Z.; Han, Z.; Ding, K.; Liu, H.; Xia, C.; Chen, J. Efficient production of methanol and diols via the hydrogenation of cyclic carbonates using copper-silica nanocomposite catalysts. Green Chem., 2015, 17, 4281-4290.
[http://dx.doi.org/10.1039/C5GC00810G]
(k) Guo, W.; Gónzalez-Fabra, J.; Bandeira, N.A.G.; Bo, C.; Kleij, A.W. A Metal-Free Synthesis of N-Aryl Carbamates under Ambient Conditions. Angew. Chem. Int. Ed. Engl., 2015, 54(40), 11686-11690.
[http://dx.doi.org/10.1002/anie.201504956] [PMID: 26385130]

Arayachukiat, S.; Kongtes, C.; Barthel, A.; Vummaleti, S.V.C.; Poater, A.; Wannakao, S.; Cavallo, L.; D’Elia, V. Ascorbic acid as a bifunctional hydrogen bond donor for the synthesis of cyclic carbonates from CO2 under ambient conditions. ACS Sustain. Chem.& Eng., 2017, 5(8), 6392-6397.
[http://dx.doi.org/10.1021/acssuschemeng.7b01650]

(a) Hicks, C.A.; Ward, M.A.; Ragumoorthy, N.; Ambler, S.J.; Dell, C.P.; Dobson, D.; O’Neill, M.J. Evaluation of glycine site antagonists of the NMDA receptor in global cerebral ischaemia. Brain Res., 1999, 819(1-2), 65-74.
[http://dx.doi.org/10.1016/S0006-8993(98)01329-8] [PMID: 10082862]
(b)Mederski, W.W.K.R.; Osswald, M.; Dorsch, D.; Christadler, M.; Schmitges, C-J.; Wilm, C. 1, 4-Diaryl-2-oxo-1, 2-dihydro-quinoline-3-carboxylic acids as endothelin receptor antagonists. Bioorg. Med. Chem. Lett., 1997, 7, 1883-1886.
[http://dx.doi.org/10.1016/S0960-894X(97)00319-3]

(a) Hewawasam, P.; Chen, N.; Ding, M.; Natale, J.T.; Boissard, C.G.; Yeola, S.; Gribkoff, V.K.; Starrett, J.; Dworetzky, S.I. The synthesis and structure-activity relationships of 3-amino-4-benzylquinolin-2-ones; discovery of novel KCNQ2 channel openers. Bioorg. Med. Chem. Lett., 2004, 14(7), 1615-1618.
[http://dx.doi.org/10.1016/j.bmcl.2004.01.073] [PMID: 15026035]
(b)Hewawasam, P.; Fan, W.; Ding, M.; Flint, K.; Cook, D.; Goggins, G.D.; Myers, R.A.; Gribkoff, V.K.; Boissard, C.G.; Dworetzky, S.I.; Starrett, J.E., Jr; Lodge, N.J. 4-Aryl-3-(hydroxyalkyl)quinolin-2-ones: novel maxi-K channel opening relaxants of corporal smooth muscle targeted for erectile dysfunction. J. Med. Chem., 2003, 46(14), 2819-2822.
[http://dx.doi.org/10.1021/jm030005h] [PMID: 12825925]
(c)Hewawasam, P.; Fan, W.; Knipe, J.; Moon, S.L.; Boissard, C.G.; Gribkoff, V.K.; Starrett, J.E. The synthesis and structure-activity relationships of 4-aryl-3-aminoquinolin-2-ones: a new class of calcium-dependent, large conductance, potassium (maxi-K) channel openers targeted for post-stroke neuroprotection. Bioorg. Med. Chem. Lett., 2002, 12(13), 1779-1783.
[http://dx.doi.org/10.1016/S0960-894X(02)00240-8] [PMID: 12067560]
(d)Raitio, K.H.; Savinainen, J.R.; Vepsäläinen, J.; Laitinen, J.T.; Poso, A.; Järvinen, T.; Nevalainen, T. Synthesis and SAR studies of 2-oxoquinoline derivatives as CB2 receptor inverse agonists. J. Med. Chem., 2006, 49(6), 2022-2027.
[http://dx.doi.org/10.1021/jm050879z] [PMID: 16539390]
(e)Cordi, A.A.; Desos, P.; Randle, J.C.R.; Lepagnol, J. Structure-activity relationships in a series of 3-sulfonylamino-2-(1H)-quinolones, as new AMPA/kainate and glycine antagonists. Bioorg. Med. Chem., 1995, 3(2), 129-141.
[http://dx.doi.org/10.1016/0968-0896(95)00007-4] [PMID: 7540921]
(f)Desos, P.; Lepagnol, J.M.; Morain, P.; Lestage, P.; Cordi, A.A. Structure-activity relationships in a series of 2(1H)-quinolones bearing different acidic function in the 3-position: 6,7-dichloro-2(1H)-oxoquinoline-3-phosphonic acid, a new potent and selective AMPA/kainate antagonist with neuroprotective properties. J. Med. Chem., 1996, 39(1), 197-206.
[http://dx.doi.org/10.1021/jm950323j] [PMID: 8568808]
(g)Carling, R.W.; Leeson, P.D.; Moore, K.W.; Smith, J.D.; Moyes, C.R.; Mawer, I.M.; Thomas, S.; Chan, T.; Baker, R.; Foster, A.C.; Grimwood, S.; Kemp, J.A.; Marshall, G.R.; Tricklebank, M.D.; Saywell, K.L. 3-Nitro-3,4-dihydro-2(1H)-quinolones. Excitatory amino acid antagonists acting at glycine-site NMDA and (RS)-alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid receptors. J. Med. Chem., 1993, 36(22), 3397-3408.
[http://dx.doi.org/10.1021/jm00074a021] [PMID: 8230130]

Buckle, D.R.; Cantello, B.C.C.; Smith, H.; Spicer, B.A. 4-hydroxy-3-nitro-2-quinolones and related compounds as inhibitors of allergic reactions. J. Med. Chem., 1975, 18(7), 726-732.
[http://dx.doi.org/10.1021/jm00241a017] [PMID: 1151993]

Cheng, P.; Zhang, Q.; Ma, Y-B.; Jiang, Z-Y.; Zhang, X-M.; Zhang, F-X.; Chen, J-J. Synthesis and in vitro anti-hepatitis B virus activities of 4-aryl-6-chloro-quinolin-2-one and 5-aryl-7-chloro-1,4-benzodiazepine derivatives. Bioorg. Med. Chem. Lett., 2008, 18(13), 3787-3789.
[http://dx.doi.org/10.1016/j.bmcl.2008.05.065] [PMID: 18524583]

Messaoudi, S.; Brion, J-D.; Alamia, M. An Expeditious Copper-Catalyzed Access to 3-Aminoquinolinones, 3-Aminocoumarins and Anilines using Sodium Azide. Adv. Synth. Catal., 2010, 352, 1677-1687.
[http://dx.doi.org/10.1002/adsc.201000149]

Khedkar, S.A.; Auti, P.B. 1, 4-Dihydropyridines: a class of pharmacologically important molecules. Mini Rev. Med. Chem., 2014, 14(3), 282-290.
[http://dx.doi.org/10.2174/1389557513666131119204126] [PMID: 24251802]

Wainwright, M. Acridine-a neglected antibacterial chromophore. J. Antimicrob. Chemother., 2001, 47(1), 1-13.
[http://dx.doi.org/10.1093/jac/47.1.1] [PMID: 11152426]

Sepehri, S.; Sanchez, H.P.; Fassihi, A. Hantzsch-Type dihydropyridines and Biginelli-type tetra-hydropyrimidines: a review of their chemotherapeutic activities. J. Pharm. Pharm. Sci., 2015, 18(1), 1-52.
[http://dx.doi.org/10.18433/J3Q01V] [PMID: 25877440]

Mikata, Y.; Yokoyama, M.; Mogami, K.; Kato, M.; Okura, I.; Chikira, M.; Yano, S. Intercalator-linked cisplatin: synthesis and antitumor activity of cis-dichloroplatinum (II) complexes connected to acridine and phenylquinolines by one methylene chain. Inorg. Chim. Acta, 1998, 279, 51-57.
[http://dx.doi.org/10.1016/S0020-1693(98)00035-8]

Berkan, O.; Saraç, B.; Simşek, R.; Yildirim, S.; Sarioğlu, Y.; Safak, C. Vasorelaxing properties of some phenylacridine type potassium channel openers in isolated rabbit thoracic arteries. Eur. J. Med. Chem., 2002, 37(6), 519-523.
[http://dx.doi.org/10.1016/S0223-5234(02)01374-0] [PMID: 12204478]

Cholody, W.M.; Horowska, B.; Paradziej-Lukowicz, J.; Martelli, S.; Konopa, J. Structure-activity relationship for antineoplastic imidazoacridinones: synthesis and antileukemic activity in vivo. J. Med. Chem., 1996, 39(5), 1028-1032.
[http://dx.doi.org/10.1021/jm950564r] [PMID: 8676337]

(a) Saha, M.; Pal, A.K. Palladium(0) nanoparticles: an efficient catalyst for the one-pot synthesis of polyhydroquinolines. Tetrahedron Lett., 2011, 52, 4872-4877.
(b)Otokesh, S.; Koukabi, N.; Kolvari, E.; Amoozadeh, A.; Malmir, M.; Azhari, S. A solvent-free synthesis of polyhydroquinolines via Hantzsch multicomponent condensation catalyzed by nanomagnetic-supported sulfonic acid. S. Afr. J. Chem., 2015, 68, 15-20.

(a) Maleki, B.; Tayebee, R.; Kermanian, M.; Ashrafi, S.S.J. One-Pot Synthesis of 1,8-Dioxodecahydroacridines and Polyhydroquinoline using 1,3-Di (bromo or chloro)-5,5-Dimethylhydantoin as a Novel and Green Catalyst under Solvent-Free Conditions. Mex. Chem. Soc., 2013, 57, 290-297.
(b)Shen, Y-B.; Wang, G-W. Solvent-free synthesis of xanthenediones and acridinediones. ARKIVOC, 2008, xvi, 1-8.
(c)Davoodnia, A.; Khashi, M.; Tavakoli-Hoseini, N. Tetrabutylammonium hexatungstate [TBA]2[W6O19]: Novel and reusable heterogeneous catalyst for rapid solvent-free synthesis of polyhydroquinoline via unsymmetrical Hantzsch reaction. Chin. J. Catal., 2013, 34, 1173-1178.
[http://dx.doi.org/10.1016/S1872-2067(12)60547-6]
(d)Khalafi-Nezhad, A.; Panahi, F.; Mohammadi, S.; Foroughi, H.O. A green and efficient procedure for one-pot synthesis of xanthenes and acridines using silica boron–sulfuric acid nanoparticles (SBSANs) as a solid Lewis-protic acid. J. Iran Chem. Soc., 2013, 10, 109-200.
[http://dx.doi.org/10.1007/s13738-012-0140-1]
(e)Soliman, H.A.; Mubarak, A.Y.; El-Merakabi, A.; Elmorsy, S.A. SiO2/ZnCl2-Catalyzed Heterocyclic Synthesis: Green, Rapid and Efficient One-Pot Synthesis of 14-H-dibenzo [a,j]Xanthenes, 1,8-Dioxo-octahydroxanthenes and 1,8-DioxoDecahydroacridines Under Solvent-Free Conditions. Chem. Sci. Trans., 2014, 3, 819-825.
(f)Vahdat, S.M.; Akbari, M. Orient. An Efficient One-Pot Synthesis of 1, 8-dioxo-Decahydroacridines by Ionic Liquid with Multi-SO3H Groups Under Ambient Temperature in Water. J. Chem., 2011, 27, 1573-1580.
(g)Tajbakhsh, M.; Alinezhad, H.; Norouzi, M.; Baghery, S.; Akbari, M. Protic pyridinium ionic liquid as a green and highly efficient catalyst for the synthesis of polyhydroquinoline derivatives via Hantzsch condensation in water. J. Mol. Liq., 2013, 177, 44-48.
[http://dx.doi.org/10.1016/j.molliq.2012.09.017]
(h)Ko, S.; Yao, C-F. Ceric ammonium nitrate (CAN) catalyzes the one-pot synthesis of polyhydroquinoline via the Hantzsch reaction. Tetrahedron, 2006, 62, 7293-7299.
[http://dx.doi.org/10.1016/j.tet.2006.05.037]

Sehout, I.; Boulcina, R.; Boumoud, B.; Boumoud, T.; Debache, A. Solvent-free synthesis of polyhydroquinoline and 1,8-dioxodecahydroacridine derivatives through the Hantzsch reaction catalyzed by a natural organic acid: A green method. Synth. Commun., 2017, 47, 1185-1191.
[http://dx.doi.org/10.1080/00397911.2017.1316406]

Jafarpour, M.; Feizpour, F.; Rezaeifard, A. Aerobic benzylic C–H oxidation catalyzed by a titania-based organic-inorganic nanohybrid. RSC Advances, 2016, 6, 54649-54660.
[http://dx.doi.org/10.1039/C6RA10191G]

(a) Kim, Y.; Kumar, M.R.; Park, N.; Heo, Y.; Lee, S. Coppercatalyzed, one-pot, three-component synthesis of benzimidazoles by condensation and C–N bond formation. J. Org. Chem., 2011, 76, 9577-9583.
(b)Brasche, G.; Buchwald, S.L. C–H functionalization/C–N bond formation: copper-catalyzed synthesis of benzimidazoles from amidines. Angew. Chem., 2008, 120, 1958-1960.
(c)Xiao, Q.; Wang, W-H.; Liu, G.; Meng, F-K.; Chen, J-H.; Yang, Z.; Shi, Z-J. Direct imidation to construct 1H-Benzo[d]imidazole through PdII-Catalyzed C-H activation promoted by thiourea. Chem. Eur. J., 2009, 15, 7292-7296.
(d)Blacker, A.J.; Farah, M.M.; Hall, M.I.; Marsden, S.P.; Saidi, O.; Williams, J.M.J. Synthesis of benzazoles by hydrogen-transfer catalysis. Org. Lett., 2009, 11, 2039-2042.
(e)Shiraishi, Y.; Sugano, Y.; Tanaka, S.; Hirai, T. One-Pot synthesis of benzimidazoles by simultaneous photocatalytic and catalytic reactions on Pt@ TiO2 nanoparticles. Angew. Chem., 122, 1700-1704.
(f)Moorthy, J.N.; Neogi, I. IBX-mediated one-pot synthesis of benzimidazoles from primary alcohols and arylmethyl bromides. Tetrahedron Lett., 2011, 52, 3868-3871.
(g)Wilfred, C.D.; Taylor, R.J.K. Preparation of 2-substituted benzimidazoles and related heterocycles directly from activated alcohols using TOP methodology. Synlett, 2004, 1628-1630.
(h)Ruiz, V.R.; Corma, A.; Sabater, M.J. New route for the synthesis of benzimidazoles by a one-pot multistep process with mono and bifunctional solid catalysts. Tetrahedron, 2010, 66, 730-735.
(i)Kondo, T.; Yang, S.; Huh, K-T.; Kobayashi, M.; Kotachi, S.; Watanabe, Y. Ruthenium complex-catalyzed facile synthesis of 2-substituted benzo-azoles. Chem. Lett., 1991, 20, 1275-1278.
(j)Raghavendra, G.M.; Ramesha, A.B.; Revanna, C.N.; Nandeesh, K.N.; Mantelingu, K.; Rangappa, K.S. One-pot tandem approach for the synthesis of benzimidazoles and benzothiazoles from alcohols. Tetrahedron Lett., 2011, 52, 5571-5574.
(k) Zhu, Y.; Jia, F.; Liu, M.; Wu, A. A multipathway coupled domino strategy: metal-free oxidative cyclization for one-pot synthesis of 2-acylbenzothiazoles from multiform substrates. Org. Lett., 2012, 14, 4414-4417.

Feizpour, F.; Jafarpour, M.; Rezaeifard, A. A Tandem Aerobic Photocatalytic Synthesis of Benzimidazoles by Cobalt Ascorbic Acid Complex Coated on TiO2 Nanoparticles Under Visible Light. Catal. Lett., 2018, 148, 30-40.
[http://dx.doi.org/10.1007/s10562-017-2232-0]

(a) Li, H.; Liu, A.; Zhao, Z.; Xu, Y.; Lin, J.; Jou, D.; Li, C. Fragment-based drug design and drug repositioning using multiple ligand simultaneous docking (MLSD): identifying celecoxib and template compounds as novel inhibitors of signal transducer and activator of transcription 3 (STAT3). J. Med. Chem., 2011, 54(15), 5592-5596.
[http://dx.doi.org/10.1021/jm101330h] [PMID: 21678971]
(b)Engelhardt, F.C.; Shi, Y-J.; Cowden, C.J.; Conlon, D.A.; Pipik, B.; Zhou, G.; McNamara, J.M.; Dolling, U-H. Synthesis of a NO-releasing prodrug of rofecoxib. J. Org. Chem., 2006, 71(2), 480-491.
[http://dx.doi.org/10.1021/jo051712g] [PMID: 16408954]
(c)Grzybowska, K.; Chmiel, K.; Knapik-Kowalczuk, J.; Grzybowski, A.; Jurkiewicz, K.; Paluch, M. Molecular factors governing the liquid and glassy states recrystallization of celecoxib in binary mixtures with excipients of different molecular weights. Mol. Pharm., 2017, 14(4), 1154-1168.
[http://dx.doi.org/10.1021/acs.molpharmaceut.6b01056] [PMID: 28241116]
(d)Bhardwaj, A.; Huang, Z.; Kaur, J.; Knaus, E.E. Rofecoxib analogues possessing a nitric oxide donor sulfohydroxamic acid (SO2NHOH) cyclooxygenase-2 pharmacophore: synthesis, molecular modeling, and biological evaluation as anti-inflammatory agents. ChemMedChem, 2012, 7(1), 62-67.
[http://dx.doi.org/10.1002/cmdc.201100393] [PMID: 21990143]
(e)Di Nunno, L.; Vitale, P.; Scilimati, A.; Tacconelli, S.; Patrignani, P. Novel synthesis of 3,4-diarylisoxazole analogues of valdecoxib: reversal cyclooxygenase-2 selectivity by sulfonamide group removal. J. Med. Chem., 2004, 47(20), 4881-4890.
[http://dx.doi.org/10.1021/jm040782x] [PMID: 15369392]
(f)Uddin, M.J.; Elleman, A.V.; Ghebreselasie, K.; Daniel, C.K.; Crews, B.C.; Nance, K.D.; Huda, T.; Marnett, L.J. Design of Fluorine-Containing 3,4-Diarylfuran-2(5H)-ones as Selective COX-1 Inhibitors. ACS Med. Chem. Lett., 2014, 5(11), 1254-1258.
[http://dx.doi.org/10.1021/ml500344j] [PMID: 25408841]

(a) Miyakoshi, H.; Miyahara, S.; Yokogawa, T.; Endoh, K.; Muto, T.; Yano, W.; Wakasa, T.; Ueno, H.; Chong, K.T.; Taguchi, J.; Nomura, M.; Takao, Y.; Fujioka, A.; Hashimoto, A.; Itou, K.; Yamamura, K.; Shuto, S.; Nagasawa, H.; Fukuoka, M. 1,2,3-Triazole-containing uracil derivatives with excellent pharmacokinetics as a novel class of potent human deoxyuridine triphosphatase inhibitors. J. Med. Chem., 2012, 55(14), 6427-6437.
[http://dx.doi.org/10.1021/jm3004174] [PMID: 22715973]
(b)Lima, C.G.S.; Ali, A.; van Berkel, S.S.; Westermann, B.; Paixão, M.W. Emerging approaches for the synthesis of triazoles: beyond metal-catalyzed and strain-promoted azide-alkyne cycloaddition. Chem. Commun. (Camb.), 2015, 51(54), 10784-10796.
[http://dx.doi.org/10.1039/C5CC04114G] [PMID: 26066359]
(c)Barve, I.J.; Thikekar, T.U.; Sun, C-M. Silver(I)-Catalyzed Regioselective Synthesis of Triazole Fused-1,5-Benzoxazocinones. Org. Lett., 2017, 19(9), 2370-2373.
[http://dx.doi.org/10.1021/acs.orglett.7b00907] [PMID: 28409630]
(d)Krasiński, A.; Fokin, V.V.; Sharpless, K.B. Direct synthesis of 1,5-disubstituted-4-magnesio-1,2,3-triazoles, revisited. Org. Lett., 2004, 6(8), 1237-1240.
[http://dx.doi.org/10.1021/ol0499203] [PMID: 15070306]
(e)Zhang, L.; Chen, X.; Xue, P.; Sun, H.H.Y.; Williams, I.D.; Sharpless, K.B.; Fokin, V.V.; Jia, G. Ruthenium-catalyzed cycloaddition of alkynes and organic azides. J. Am. Chem. Soc., 2005, 127(46), 15998-15999.
[http://dx.doi.org/10.1021/ja054114s] [PMID: 16287266]
(f)Cheng, G.; Zeng, X.; Shen, J.; Wang, X.; Cui, X. A metal-free multicomponent cascade reaction for the regiospecific synthesis of 1,5-disubstituted 1,2,3-triazoles. Angew. Chem. Int. Ed. Engl., 2013, 52(50), 13265-13268.
[http://dx.doi.org/10.1002/anie.201307499] [PMID: 24227395]
(g)Kim, W.G.; Kang, M.E.; Lee, J.B.; Jeon, M.H.; Lee, S.; Lee, J.; Choi, B.; Cal, P.M.S.D.; Kang, S.; Kee, J-M.; Bernardes, G.J.L.; Rohde, J-U.; Choe, W.; Hong, S.Y. Nickel-catalyzed azide–alkyne cycloaddition to access 1, 5-disubstituted 1, 2, 3-triazoles in air and water. J. Am. Chem. Soc., 2017, 139(35), 12121-12124.
[http://dx.doi.org/10.1021/jacs.7b06338] [PMID: 28814075]

Kumar, N.; Ansari, M.Y.; Kant, R.; Kumar, A. Copper-catalyzed decarboxylative regioselective synthesis of 1,5-disubstituted 1,2,3-triazoles. Chem. Commun. (Camb.), 2018, 54(21), 2627-2630.
[http://dx.doi.org/10.1039/C7CC09934G] [PMID: 29468231]

Shaabani, A.; Khodkari, V.; Nazeri, M.T.; Ghasemi, S.; Mohammadian, R.; Shaabani, S. Vitamin C as a green and robust catalyst for the fast and efficient synthesis of valuable organic compounds via multi-component reactions in water. J. Iran. Chem. Soc., 2019, 16, 1793-1800.
[http://dx.doi.org/10.1007/s13738-019-01655-w]

Sangshetti, J.N.; Zambare, A.S.; Khan, F.A.; Gonjari, I.; Zaheer, Z. Synthesis and biological activity of substituted-4,5,6,7-tetrahydrothieno pyridines: a review. Mini Rev. Med. Chem., 2014, 14(12), 988-1020.
[http://dx.doi.org/10.2174/1389557514666141106131425] [PMID: 25373848]

(a) Archer, G.A.; Sternbach, L.H. Chemistry of benzodiazepines. Chem. Rev., 1968, 68, 747-748.
[http://dx.doi.org/10.1021/cr60256a004]
(b)Shaabani, A.; Maleki, A.; Mofakham, H. Novel multicomponent one-pot synthesis of tetrahydro-1H-1,5-benzodiazepine-2-carboxamide derivatives. J. Comb. Chem., 2008, 10(4), 595-598.
[http://dx.doi.org/10.1021/cc8000635] [PMID: 18553983]

(a) Lengar, A.; Kappe, C.O. Tunable carbon-carbon and carbon-sulfur cross-coupling of boronic acids with 3,4-dihydropyrimidine-2-thiones. Org. Lett., 2004, 6(5), 771-774.
[http://dx.doi.org/10.1021/ol036496h] [PMID: 14986971]
(b)Deres, K.; Schröder, C.H.; Paessens, A.; Goldmann, S.; Hacker, H.J.; Weber, O.; Krämer, T.; Niewöhner, U.; Pleiss, U.; Stoltefuss, J.; Graef, E.; Koletzki, D.; Masantschek, R.N.; Reimann, A.; Jaeger, R.; Gross, R.; Beckermann, B.; Schlemmer, K.H.; Haebich, D.; Rübsamen-Waigmann, H. Inhibition of hepatitis B virus replication by drug-induced depletion of nucleocapsids. Science, 2003, 299(5608), 893-896.
[http://dx.doi.org/10.1126/science.1077215] [PMID: 12574631]

(a) Atwal, K.S.; Swanson, B.N.; Unger, S.E.; Floyd, D.M.; Moreland, S.; Hedberg, A.; O’Reilly, B.C. Dihydropyrimidine calcium channel blockers. 3. 3-Carbamoyl-4-aryl-1,2,3,4-tetrahydro-6-methyl-5-pyrimidinecarboxylic acid esters as orally effective antihypertensive agents. J. Med. Chem., 1991, 34(2), 806-811.
[http://dx.doi.org/10.1021/jm00106a048] [PMID: 1995904]
(b)Bahekar, S.S.; Shinde, D.B. Synthesis and anti-inflammatory activity of some [4,6-(4-substituted aryl)-2-thioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]-acetic acid derivatives. Bioorg. Med. Chem. Lett., 2004, 14(7), 1733-1736.
[http://dx.doi.org/10.1016/j.bmcl.2004.01.039] [PMID: 15026060]
(c)Kappe, C.O. Biologically active dihydropyrimidones of the Biginelli-type--a literature survey. Eur. J. Med. Chem., 2000, 35(12), 1043-1052.
[http://dx.doi.org/10.1016/S0223-5234(00)01189-2] [PMID: 11248403]
(d)Kappe, C.O. The generation of dihydropyrimidine libraries utilizing Biginelli multicomponent chemistry. QSAR Comb. Sci., 2003, 22, 630-645.
[http://dx.doi.org/10.1002/qsar.200320001]
(e)Rovnyak, G.C.; Atwal, K.S.; Hedberg, A.; Kimball, S.D.; Moreland, S.; Gougoutas, J.Z.; O’Reilly, B.C.; Schwartz, J.; Malley, M.F. Dihydropyrimidine calcium channel blockers. 4. Basic 3-substituted-4-aryl-1,4-dihydropyrimidine-5-carboxylic acid esters. Potent antihypertensive agents. J. Med. Chem., 1992, 35(17), 3254-3263.
[http://dx.doi.org/10.1021/jm00095a023] [PMID: 1387168]

Nagarathnam, D.; Miao, S.W.; Lagu, B.; Chiu, G.; Fang, J.; Murali Dhar, T.G.; Zhang, J.; Tyagarajan, S.; Marzabadi, M.R.; Zhang, F.; Wong, W.C.; Sun, W.; Tian, D.; Wetzel, J.M.; Forray, C.; Chang, R.S.; Broten, T.P.; Ransom, R.W.; Schorn, T.W.; Chen, T.B.; O’Malley, S.; Kling, P.; Schneck, K.; Bendesky, R.; Harrell, C.M. Design and synthesis of novel alpha(1)(a) adrenoceptor-selective antagonists. 1. Structure-activity relationship in dihydropyrimidinones. J. Med. Chem., 1999, 42(23), 4764-4777.
[http://dx.doi.org/10.1021/jm990200p] [PMID: 10579840]

Biginelli, P. Derivati Aldeiduredici Eteri Acetile Dossal-Acetico. Gazz. Chim. Ital., 1893, 23, 360-416.

(a) Sandhu, S.J.S. Past, present and future of the Biginelli reaction: a critical perspective. ARKIVOC, 2012, (i), 66-133.
(b)Bigdeli, M.A.; Jafari, S.; Mahdavinia, G.H.; Hazarkhan, H. Trichloroisocyanuric acid, a new and efficient catalyst for the synthesis of dihydropyrimidinones. Catal. Commun., 2007, 8, 1641-1644.
[http://dx.doi.org/10.1016/j.catcom.2007.01.022]
(c)De, S.K.; Gibbs, R.A. Ruthenium (III) chloride-catalyzed one-pot synthesis of 3,4-dihydropyrimidin-2-(1H)-ones under solvent-free conditions. Synthesis, 2005, 1748-1450.
[http://dx.doi.org/10.1055/s-2005-869899]
(d)Sharghi, H.; Jokar, M. Al2O3/MeSO3H: A Novel and Recyclable Catalyst for One-Pot Synthesis of 3,4-Dihydropyrimidinones or Their Sulfur Derivatives in Biginelli Condensation. Lett. Org. Chem., 2012, 9, 12-18.
(e)Mandhane, P.G.; Joshi, R.S.; Nagargoje, D.R.; Gill, C.H. An efficient synthesis of 3,4-dihydropyrimidin-2(1H)-ones catalyzed by thiamine hydrochloride in water under ultrasound irradiation. Tetrahedron Lett., 2010, 51, 3138-3140.
[http://dx.doi.org/10.1016/j.tetlet.2010.04.037]
(f)Murata, H.; Ishitani, H.; Iwamoto, M. Synthesis of Biginelli dihydropyrimidinone derivatives with various substituents on aluminium-planted mesoporous silica catalyst. Org. Biomol. Chem., 2010, 8(5), 1202-1211.
[http://dx.doi.org/10.1039/b920821f] [PMID: 20165814]
(g)Lu, J.; Bai, Y. Catalysis of the Biginelli reaction by ferric and nickel chloride hexahydrates. One-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones. Synthesis, 2002, 4, 466-470.
[http://dx.doi.org/10.1055/s-2002-20956]

Sehout, I.; Boulcina, R.; Boumoud, B.; Berrée, F.; Carboni, F.; Debache, A. Ascorbic acid-catalyzed one-pot three-component Biginelli reaction: a practical and green approach towards synthesis of 3, 4-dihydropyrimidin-2 (1H)-ones/thiones. Lett. Org. Chem., 2013, 10, 463-467.
[http://dx.doi.org/10.2174/15701786113109990014]

Mohamadpour, F. Ascorbic acid as a natural green, highly efficient and economical catalyst promoted one-pot facile synthesis of 12-aryl-tetrahydrobenzo[A]xanthene-11-ones, 1,8-dioxo-octahydroxa-nthenes and 14-aryl-14H-dibenzo[A,J]xanthenes under solvent-free conditions. UPB Scientific Bulletin, Series B. Chemistry and Materials Science, 2018, 80, 101-116.