Generic placeholder image

Current Organic Chemistry


ISSN (Print): 1385-2728
ISSN (Online): 1875-5348

Review Article

Diaryliodonium Salts: Structures and Synthesis

Author(s): Yu Wang, Guoqiang An, Limin Wang* and Jianwei Han*

Volume 24, Issue 18, 2020

Page: [2070 - 2105] Pages: 36

DOI: 10.2174/1385272824999200507124328

Price: $65


Due to similar reactivity in comparison with aromatic organometallic reagents, diaryliodonium salts are currently in broad usage as less toxic, highly efficient, stable and mild electrophilic reagents in organic synthesis. The hypervalent iodine center of diaryliodonium salts can lead to unique reactivity, which thus is frequently presented in metal-free arylations or metal-involved elementary reactions such as oxidative addition, reduction elimination, ligand coupling and ligand exchange reaction. As such, diaryliodonium salts have experienced explosive growth by transferring aromatics to the target molecules. In contrast to the reviews on the synthetic utility or aryl transformations by using diaryliodonium salts, this review provides a summary of their structures and the synthetic strategies towards them during recent decades.

Keywords: Diaryliodonium salts, hypervalent iodine, T-shaped structure, synthetic strategies, cyclic or linear, organometallic reagents.

Graphical Abstract
Aradi, K.; Tόth, B.L.; Tolnai, G.L.; Novák, Z. Diaryliodonium salts in organic syntheses: a useful compound class for novel arylation strategies. Synlett, 2016, 27, 1356-1458.
Wirth, T. Hypervalent iodine chemistry in synthesis: scope and new directions. Angew. Chem. Int. Ed. Engl., 2005, 44(24), 3656-3665.
[] [PMID: 15828037]
Farid, U.; Malmedy, F.; Claveau, R.; Albers, L.; Wirth, T. Stereoselective rearrangements with chiral hypervalent iodine reagents. Angew. Chem. Int. Ed. Engl., 2013, 52(27), 7018-7022.
[] [PMID: 23653165]
Shao, X.; Wang, X.; Yang, T.; Lu, L.; Shen, Q. An electrophilic hypervalent iodine reagent for trifluoromethylthiolation. Angew. Chem. Int. Ed. Engl., 2013, 52(12), 3457-3460.
[] [PMID: 23355233]
Maity, A.; Hyun, S.M.; Powers, D.C. Oxidase catalysis via aerobically generated hypervalent iodine intermediates. Nat. Chem., 2018, 10(2), 200-204.
[] [PMID: 29359760]
Zhdankin, V.V.; Protasiewicz, J.D. Development of new hypervalent iodine reagents with improved properties and reactivity by redirecting secondary bonds at iodine center. Coord. Chem. Rev., 2014, 275, 54-62.
Dohi, T.; Kita, Y. Metal-free oxidative biaryl coupling by hypervalent iodine reagents. Curr. Org. Chem., 2016, 20, 580-615.
Yusubov, N.S.; Zhdankin, V.V. Hypervalent iodine reagents and green chemistry. Curr. Org. Chem., 2012, 9, 242-272.
Gao, G.; Chen, Q. Recent advances in utilities of active iodine reagents as organo- catalysts in organic synthesis. Curr. Org. Chem., 2017, 4, 33-47.
Zhdankin, V.V. Benziodoxole-based hypervalent iodine reagents in organic synthesis. Curr. Org. Chem., 2005, 2, 121-145.
Xing, L.; Zhang, Y.; Du, Y. Hypervalent iodine-mediated synthesis of spiroheterocycles via oxidative cyclization. Curr. Org. Chem., 2019, 23, 14-37.
Li, X.; Liu, T.; Zhang, B.; Zhang, D.; Shi, H.; Yu, Z.; Tao, S.; Du, Y. Formation of carbon-carbon bonds mediated by hypervalent iodine reagents under metal-free conditions. Curr. Org. Chem., 2020, 24, 74-103.
Moreno, I.; Tellitu, I.; Herrero, M.T.; SanMartin, R.; Dominguez, E. New perspectives for iodine (III) reagents in (hetero)biaryl coupling reactions. Curr. Org. Chem., 2002, 6, 1433-1452.
Kupwade, R.V. A concise review of hypervalent iodine with special reference to Dess- Martin periodinane. Mini Rev. Org. Chem., 2020, 17, 1-11.
Juvenal, J.G.; Thomasz, L.; Oglio, R.; Perona, M.; Pisarev, M.A.; Rossich, L.; Salvarredi, L. Thyroid: iodine beyond the thyronines. Curr. Chem. Biol., 2011, 5, 163-167.
Merritt, E.A.; Olofsson, B. Diaryliodonium salts: a journey from obscurity to fame. Angew. Chem. Int. Ed. Engl., 2009, 48(48), 9052-9070.
[] [PMID: 19876992]
Phipps, R.J.; McMurray, L.; Ritter, S.; Duong, H.A.; Gaunt, M.J. Copper-catalyzed alkene arylation with diaryliodonium salts. J. Am. Chem. Soc., 2012, 134(26), 10773-10776.
[] [PMID: 22712572]
Wu, X.; Yang, Y.; Han, J.; Wang, L. Palladium catalyzed C-I and vicinal C-H dual activation of diaryliodonium salts for diarylation: synthesis of 4,5-benzocoumarins. Org. Lett., 2015, 17(22), 5654-5657.
[] [PMID: 26523622]
Qian, X.; Han, J.; Wang, L. Palladium catalyzed C–I and vicinal C–H dual activation of diaryliodonium salts for diarylations: synthesis of triphenylenes. Adv. Synth. Catal., 2016, 358, 940-946.
Wu, X.; Han, J.; Wang, L. Palladium catalyzed C-I and vicinal C-H dual activation of diaryliodonium salts for diarylations: synthesis of triphenylenes. J. Org. Chem., 2018, 83(1), 49-56.
[] [PMID: 29171754]
Chen, H.; Han, J.; Wang, L. Diels-Alder cycloadditions of N-arylpyrroles via aryne intermediates using diaryliodonium salts. Beilstein J. Org. Chem., 2018, 14, 354-363.
[] [PMID: 29507640]
Xu, B. Han. J.; Wang, L. Metal- and base-free direct n-arylation of pyridazinones by diaryliodonium salts: an anion effect. Asian J. Org. Chem., 2018, 7, 1674-1680.
Cui, L.; Chen, H.; Ma, J.; Han, J.; Wang, L. Synthesis of vicinal trifluoromethanesulfonate substituted diaryliodonium salts and their anti-bacterial properties. Youji Huaxue, 2019, 39, 270-276.
Goldstein, E.J.C.; Citron, D.M.; Warren, Y.; Merriam, C.V.; Tyrrell, K.; Fernandez, H.; Radhakrishnan, U.; Stang, P.J.; Conrads, G. In vitro activities of iodonium salts against oral and dental anaerobes. Antimicrob. Agents Chemother., 2004, 48(7), 2766-2770.
[] [PMID: 15215147]
Hartmann, C.; Meyer, V. Ueber die Jodoniumbasen. Ber. Dtsch. Chem. Ges., 1894, 27, 426-426.
Alcock, N.W.; Country, R.M. Secondary bonding. Part I. Crystal and molecular structures of Ph2IX (X = CI, Br, or I). J. Chem. Soc., Dalton Trans., 1977, 217-219.
Lyons, T.W.; Sanford, M.S. Palladium-catalyzed ligand-directed C-H functionalization reactions. Chem. Rev., 2010, 110(2), 1147-1169.
[] [PMID: 20078038]
Crivello, J.V.; Lee, J.L. Alkoxy-substituted diaryliodonium salt cationic photoinitiators. J. Photopolym. Sci. Technol., 1990, 3, 327-334.
Olofsson, B. Arylation with diaryliodonium salts. Top. Curr. Chem. (Cham), 2016, 373, 135-166.
Yoshimura, A.; Saito, A.; Zhdankin, V.V. Iodonium salts as benzyne precursors. Chemistry, 2018, 24(57), 15156-15166.
[] [PMID: 29797627]
Zhdankin, V.V.; Stang, P.J. Recent developments in the chemistry of polyvalent iodine compounds. Chem. Rev., 2002, 102(7), 2523-2584.
[] [PMID: 12105935]
Zhdankin, V.V.; Stang, P.J. Chemistry of polyvalent iodine. Chem. Rev., 2008, 108(12), 5299-5358.
[] [PMID: 18986207]
Yoshimura, A.; Zhdankin, V.V. Advances in synthetic applications of hypervalent iodine compounds. Chem. Rev., 2016, 116(5), 3328-3435.
[] [PMID: 26861673]
Aradi, K.; Tóth, B.L.; Tolnai, G.L.; Novák, Z. Diaryliodonium salts in organic syntheses: a useful compound class for novel arylation strategies. Synlett, 2016, 27, 1456-1485.
Cao, C.K.; Sheng, J.; Chen, C. Cu-Catalyzed cascade annulation of diaryliodonium salts and nitriles: synthesis of nitrogen-containing heterocycles. Synthesis, 2017, 49, 5081-5092.
Fañanás-Mastral, M. Copper-catalyzed arylation with diaryliodonium salts. Synthesis, 2017, 49, 1905-1930.
Stuart, D.R. Aryl transfer selectivity in metal-free reactions of unsymmetrical diaryliodonium salts. Chemistry, 2017, 23(63), 15852-15863.
[] [PMID: 28793179]
Duan, Y.; Jiang, S.; Han, Y.; Sun, B.; Zhang, C. Recent advances in hypervalent iodine chemistry. Youji Huaxue, 2016, 36, 1973-1984.
Beringer, F.M.; Brierley, A.; Drexler, M.; Gindler, E.M.; Lumpkin, C.C. Diaryliodonium salts. I. Synthesis. J. Am. Chem. Soc., 1953, 75, 2705-2708.
Beringer, F.M.; Falk, R.A.; Karniol, M.; Lillien, I.; Masullo, G.; Mausner, M.; Sommer, E. Diaryliodonium salts. IX. The synthesis of substituted diphenyliodonium salts. J. Am. Chem. Soc., 1959, 81, 342-342.
Bielawski, M.; Olofsson, B. High-yielding one-pot synthesis of diaryliodonium triflates from arenes and iodine or aryl iodides. Chem. Commun. (Camb.), 2007, 2007(24), 2521-2523.
[] [PMID: 17563816]
Zhu, M.; Jalalian, N.; Olofsson, B. One-pot synthesis of diaryliodonium salts using toluenesulfonic acid: a fast entry to electron-rich diaryliodonium tosylates and triflates. Synlett, 2008, 4, 592-596.
Bielawski, M.; Aili, D.; Olofsson, B. Regiospecific one-pot synthesis of diaryliodonium tetrafluoroborates from arylboronic acids and aryl iodides. J. Org. Chem., 2008, 73(12), 4602-4607.
[] [PMID: 18505294]
Kraszkiewicz, L.; Skulski, L. Facile syntheses of symmetrical diaryliodonium salts from various arenes, with sodium metaperiodate as the coupling reagent in acidic media. Synthesis, 2008, 15, 2373-2380.
Cardinale, J.; Ermert, J.; Coenen, H.H. Convenient preparation of (4-iodophenyl) aryliodonium salts. Tetrahedron, 2012, 68, 4112-4116.
Wüst, F.R.; Kniess, T. Synthesis of 4-[18F]fluoroiodobenzene and its application in Sonogashira cross-coupling reactions. J. Labelled Comp. Radiopharm., 2003, 46, 699-713.
Wagner, A.M.; Sanford, M.S. Palladium-catalyzed C-H arylation of 2,5-substituted pyrroles. Org. Lett., 2011, 13(2), 288-291.
[] [PMID: 21141808]
Zhu, H.; Liu, X.; Cheng, Y.; Peng, H.; Liu, Y.; Dong, Z. Copper-catalyzed S-arylation of arylthioureas by using diaryliodonium salts. Synthesis, 2018, 50, 2247-2254.
Ghosh, M.K.; Rzymkowski, J.; Kalek, M. Transition-metal-free aryl-aryl cross-coupling: C-H arylation of 2-naphthols with diaryliodonium salts. Chemistry, 2019, 25(41), 9619-9623.
[] [PMID: 31162732]
Jalalian, N.; Petersen, T.B.; Olofsson, B. Metal-free arylation of oxygen nucleophiles with diaryliodonium salts. Chemistry, 2012, 18(44), 14140-14149.
[] [PMID: 23015511]
Crivello, J.V.; Lam, J.H.W. Diaryliodonium salts. A new class of photoinitiators for cationic polymerization. Macromolecules, 1977, 6, 1307-1315.
Malmgren, J.; Santoro, S.; Jalalian, N.; Himo, F.; Olofsson, B. Arylation with unsymmetrical diaryliodonium salts: a chemoselectivity study. Chemistry, 2013, 19(31), 10334-10342.
[] [PMID: 23788251]
Beringer, F.M.; Huang, S.J. Rearrangement and cleavage of 2-aryliodoniobenzoates. Trapping agents for benzyne. J. Org. Chem., 1964, 29, 445-448.
Shah, A.; Pike, V.W.; Widdowson, D.A. Synthesis of functionalised unsymmetrical diaryliodonium salts. J. Chem. Soc. Perkin Trans., 1997, 1, 2463-2465.
Pike, V.W.; Butt, F.; Shah, A.; Widdowson, D.A. Facile synthesis of substituted diaryliodonium tosylates by treatment of aryltributylstannanes with Koser’s reagent. J. Chem. Soc. Perkin Trans., 1999, 1, 245-248.
Carroll, M.A.; Pike, V.W.; Widdowson, D.A. New synthesis of diaryliodonium sulfonates from arylboronic acids. Tetrahedron Lett., 2000, 41, 5393-5396.
Kita, Y.; Morimoto, K.; Ito, M.; Ogama, C.; Goto, A.; Dohi, T. Metal-free oxidative cross-coupling of unfunctionalized aromatic compound. J. Am. Chem. Soc., 2009, 131, 1688-1669.
Dohi, T.; Ito, M.; Yamaoka, N.; Morimoto, K.; Fujioka, H.; Kita, Y. Unusual ipso substitution of diaryliodonium bromides initiated by a single-electron-transfer oxidizing process. Angew. Chem. Int. Ed. Engl., 2010, 49(19), 3334-3337.
[] [PMID: 20405520]
Wang, B.; Cerny, R.L.; Uppaluri, S.; Kempinger, J.J.; Dimagno, S.G. Fluoride-promoted ligand exchange in diaryliodonium salts. J. Fluor. Chem., 2010, 131(11), 1113-1121.
[] [PMID: 21057607]
Graskemper, J.W.; Wang, B.; Qin, L.; Neumann, K.D.; DiMagno, S.G. Unprecedented directing group ability of cyclophanes in arene fluorinations with diaryliodonium salts. Org. Lett., 2011, 13(12), 3158-3161.
[] [PMID: 21591627]
Moon, B.S.; Kil, H.S.; Park, J.H.; Kim, J.S.; Park, J.; Chi, D.Y.; Lee, B.C.; Kim, S.E. Facile aromatic radiofluorination of [18F]flumazenil from diaryliodonium salts with evaluation of their stability and selectivity. Org. Biomol. Chem., 2011, 9(24), 8346-8355.
[] [PMID: 22057475]
Chun, J.H.; Pike, V.W. Regiospecific syntheses of functionalized diaryliodonium tosylates via [hydroxy(tosyloxy)iodo]arenes generated in situ from (diacetoxyiodo)arenes. J. Org. Chem., 2012, 77(4), 1931-1938.
[] [PMID: 22276914]
Dohi, T.; Yamaoka, N.; Itani, I.; Kita, Y. One-pot syntheses of diaryliodonium salts from aryl iodides using peracetic acid as green oxidant. Aust. J. Chem., 2011, 64, 529-535.
Ito, M.; Itani, I.; Toyoda, Y.; Morimoto, K.; Dohi, T.; Kita, Y. Synthesis of boron-substituted diaryliodonium salts and selective transformation into functionalized aryl boronates. Angew. Chem. Int. Ed. Engl., 2012, 51(50), 12555-12558.
[] [PMID: 23139190]
Landge, K.P.; Jang, K.S.; Lee, S.Y.; Chi, D.Y. Approach to the synthesis of indoline derivatives from diaryliodonium salts. J. Org. Chem., 2012, 77(13), 5705-5713.
[] [PMID: 22670828]
Toh, Q.Y.; McNally, A.; Vera, S.; Erdmann, N.; Gaunt, M.J. Organocatalytic C-H bond arylation of aldehydes to bis-heteroaryl ketones. J. Am. Chem. Soc., 2013, 135(10), 3772-3775.
[] [PMID: 23445238]
Bielawski, M.; Malmgren, J.; Pardo, L.M.; Wikmark, Y.; Olofsson, B. One-pot synthesis and applications of N-heteroaryl iodonium salts. ChemistryOpen, 2014, 3(1), 19-22.
[] [PMID: 24688890]
Matsuzaki, K.; Okuyama, K.; Tokunaga, E.; Shiro, M.; Shibata, N. Sterically demanding unsymmetrical diaryl-λ3-iodanes for electrophilic pentafluorophenylation and an approach to α-pentafluorophenyl carbonyl compounds with an all-carbon stereocenter. ChemistryOpen, 2014, 3(6), 233-237.
[] [PMID: 25558441]
(a)13th National Meeting on Fluorine Chemistry of China; Shanghai,, August, 20-23, 2014; p. 53.
(b)Zhang, Y-X. Master thesis,. Shanghai Institute of Technology, 2016.
Zhang, Y.; Han, J.; Liu, J. Diaryliodonium salts as eicient lewis acid catalysts for direct three component Mannich reactions. RSC Advances, 2015, 5, 25485-25488.
Matsuzaki, K.; Okuyama, K.; Tokunaga, E.; Saito, N.; Shiro, M.; Shibata, N. Synthesis of diaryliodonium salts having pentafluorosulfanylarenes and their application to electrophilic pentafluorosulfanylarylation of C-, O-, N-, and S-nucleophiles. Org. Lett., 2015, 17(12), 3038-3041.
[] [PMID: 26023887]
Das, P.; Takada, M.; Matsuzaki, K.; Saito, N.; Shibata, N. SF5-Pyridylaryl-λ3-iodonium salts and their utility as electrophilic reagents to access SF5-pyridine derivatives in the late-stage of synthesis. Chem. Commun. (Camb.), 2017, 53(27), 3850-3853.
[] [PMID: 28317050]
Wu, Y.; Izquierdo, S.; Vidossich, P.; Lledós, A.; Shafir, A. NH-Heterocyclic aryliodonium salts and their selective conversion into N1-Aryl-5-iodoimidazoles. Angew. Chem. Int. Ed. Engl., 2016, 55(25), 7152-7156.
[] [PMID: 27142566]
Seidl, T.L.; Sundalam, S.K.; McCullough, B.; Stuart, D.R. Unsymmetrical aryl(2,4,6-trimethoxyphenyl)iodonium salts: one-pot synthesis, scope, stability, and synthetic studies. J. Org. Chem., 2016, 81(5), 1998-2009.
[] [PMID: 26828570]
Koseki, D.; Aoto, E.; Shoji, T.; Watanabe, K. In, Y.; Kita, Y.; Dohi T. Efficient N-arylation of azole compounds utilizing selective aryl-transfer TMP-iodonium(III) reagents. Tetrahedron Lett., 2019, 60, 1281-1286.
Lindstedt, E.; Reitti, M.; Olofsson, B. One-pot synthesis of unsymmetric diaryliodonium salts from iodine and arenes. J. Org. Chem., 2017, 82(22), 11909-11914.
[] [PMID: 28809562]
Laudadio, G.; Gemoets, H.P.L.; Hessel, V.; Noël, T. Flow synthesis of diaryliodonium triflates. J. Org. Chem., 2017, 82(22), 11735-11741.
[] [PMID: 28695736]
Mazza, D.D.; Reinecke, M.G. Thiophenes as traps for benzyne. 1. The role of the precursor. J. Org. Chem., 1988, 53, 5799-5806.
Kitamura, T.; Yamane, M. (Phenyl)[o-(trimethylsilyi)phenyl]iodonium triflate. A new and efficient precursor of benzyne. J. Chem. Soc. Chem. Commun., 1995, 983-984.
Kitamura, T.; Yamane, M.; Inoue, K.; Todaka, M.; Fukatsu, N. A new and efficient hypervalent iodine-benzyne precursor, (phenyl)[o-(trimethylsilyl)-phenyl] iodonium triflate: generation, trapping reaction, and nature of benzyne. J. Am. Chem. Soc., 1999, 121, 11674-11679.
Kitamura, T.; Gondo, K.; Oyamada, J. Hypervalent iodine/triflate hybrid benzdiyne equivalents: access to controlled synthesis of polycyclic aromatic compounds. J. Am. Chem. Soc., 2017, 139(25), 8416-8419.
[] [PMID: 28613858]
Yoshimura, A.; Fuchs, J.M.; Middleton, K.R.; Maskaev, A.V.; Rohde, G.T.; Saito, A.; Postnikov, P.S.; Yusubov, M.S.; Nemykin, V.N.; Zhdankin, V.V. Pseudocyclic arylbenziodoxaboroles: efficient benzyne precursors triggered by water at room temperature. Chemistry, 2017, 23(66), 16738-16742.
[] [PMID: 28981177]
Robidas, R.; Guérin, V.; Provençal, L.; Echeverria, M.; Legault, C.Y. Investigation of iodonium trifluoroborate zwitterions as bifunctional arene reagents. Org. Lett., 2017, 19(23), 6420-6423.
[] [PMID: 29144752]
Xie, F.; Zhang, Z.; Yu, X.; Tang, G.; Li, X. Diaryliodoniums by rhodium(III)-catalyzed C-H activation: mild synthesis and diversified functionalizations. Angew. Chem. Int. Ed. Engl., 2015, 54(25), 7405-7409.
[] [PMID: 25959273]
Linstad, E.J.; Vāvere, A.L.; Hu, B.; Kempinger, J.J.; Snyder, S.E.; DiMagno, S.G. Thermolysis and radiofluorination of diaryliodonium salts derived from anilines. Org. Biomol. Chem., 2017, 15(10), 2246-2252.
[] [PMID: 28230886]
Chen, H.; Han, J.; Wang, L. Intramolecular aryl migration of diaryliodonium salts: access to ortho-iodo diaryl ethers. Angew. Chem. Int. Ed. Engl., 2018, 57(38), 12313-12317.
[] [PMID: 30137685]
Yoshimura, A.; Shea, M.T.; Guselnikova, O.; Postnikov, P.S.; Rohde, G.T.; Saito, A.; Yusubov, M.S.; Nemykin, V.N.; Zhdankin, V.V. Preparation and structure of phenolic aryliodonium salts. Chem. Commun. (Camb.), 2018, 54(73), 10363-10366.
[] [PMID: 30152483]
Sadek, O.; Perrin, D.M.; Gras, E. Unsymmetrical diaryliodonium phenyltrifluoroborate salts: synthesis, structure and fluorination. J. Fluor. Chem., 2019, 222-223, 68-74.
Dohi, T.; Hayashi, T.; Ueda, S.; Shoji, T.; Komiyama, K.; Takeuchi, H.; Kita, Y. Recyclable synthesis of mesityl iodonium(III) salts. Tetrahedron, 2019, 75, 3617-3627.
Chatterjee, N.; Goswami, A. Synthesis and application of cyclic diaryliodonium salts: a platform for bifunctionalization in a single step. Eur. J. Org. Chem., 2017, 21, 3023-3032.
Collette, J.; McGreer, D.; Crawford, R.; Chubb, F.; Sandin, R.B. Synthesis of cyclic iodonium salts containing an asymmetric carbon atom. J. Am. Chem. Soc., 1956, 78, 3819-3820.
Koser, G.F.; Wettaoh, R.H. New methodology in iodonium salt synthesis. Reactions of [hydroxy(tosyloxy)iodo]arenes with aryltrimethylsilanes. J. Org. Chem., 1980, 45, 1543-1544.
Liu, Z.; Zhu, D.; Luo, B.; Zhang, N.; Liu, Q.; Hu, Y.; Pi, R.; Huang, P.; Wen, S. Mild Cu(I)-catalyzed cascade reaction of cyclic diaryliodoniums, sodium azide, and alkynes: efficient synthesis of triazolophenanthridines. Org. Lett., 2014, 16(21), 5600-5603.
[] [PMID: 25338129]
Vlasenko, Y.A.; Postnikov, P.S.; Trusova, M.E.; Shafir, A.; Zhdankin, V.V.; Yoshimura, A.; Yusubov, M.S. Synthesis of five-membered iodine-nitrogen heterocycles from benzimidazole-based iodonium salts. J. Org. Chem., 2018, 83(19), 12056-12070.
[] [PMID: 30205009]
Postnikov, P.S.; Guselnikova, O.A.; Yusubov, M.S.; Yoshimura, A.; Nemykin, V.N.; Zhdankin, V.V. One-pot synthesis of diaryliodonium salts from arenes and aryl iodides with oxone–sulfuric acid. J. Org. Chem., 2015, 80, 5783-5788.
[] [PMID: 25951091]
Wang, M.; Chen, S.; Jiang, X. Construction of functionalized annulated sulfone via SO2/I exchange of cyclic diaryliodonium salts. Org. Lett., 2017, 19(18), 4916-4919.
[] [PMID: 28876937]
Wang, M.; Wei, J.; Fan, Q.; Jiang, X. Cu(II)-catalyzed sulfide construction: both aryl groups utilization of intermolecular and intramolecular diaryliodonium salt. Chem. Commun. (Camb.), 2017, 53(20), 2918-2921.
[] [PMID: 28165512]
Wang, M.; Fan, Q.; Jiang, X. Nitrogen-iodine exchange of diaryliodonium salts: access to acridine and carbazole. Org. Lett., 2018, 20(1), 216-219.
[] [PMID: 29256611]
Yang, S.; Wang, F.; Wu, Y.; Hua, W.; Zhang, F. Synthesis of functionalized triphenylenes via a traceless directing group strategy. Org. Lett., 2018, 20(6), 1491-1495.
[] [PMID: 29516740]
Yang, S.; Hua, W.; Wu, Y.; Hu, T.; Wang, F.; Zhang, X.; Zhang, F. Site-selective synthesis of functionalized dibenzo[f,h]quinolines and their derivatives involving cyclic diaryliodonium salts via a decarboxylative annulation strategy. Chem. Commun. (Camb.), 2018, 54(26), 3239-3242.
[] [PMID: 29536069]
Xie, H.; Ding, M.; Liu, M.; Hu, T.; Zhang, F. Synthesis of functionalized biaryls and poly(hetero)aryl containing medium-sized lactones with cyclic diaryliodonium salts. Org. Lett., 2017, 19(10), 2600-2603.
[] [PMID: 28481117]
Li, J.; Xu, Q.N.; Wang, Z.B.; Li, Y.; Liu, L. Synthesis of dibenzofurans from cyclic diaryliodonium triflates and water via oxygen-iodine exchange approach. ACS Omega, 2018, 3(10), 12923-12929.
[] [PMID: 31458015]
Zhang, Y.; Han, J.; Liu, Z-J. Palladium-catalyzed double-Suzuki-Miyaura reactions using cyclic dibenziodoniums: synthesis of o-tetraaryls. J. Org. Chem., 2016, 81(4), 1317-1323.
[] [PMID: 26608348]
Li, B.; Chao, Z.; Li, C.; Gu, Z. Cu-Catalyzed enantioselective ring opening of cyclic diaryliodoniums toward the synthesis of chiral diarylmethanes. J. Am. Chem. Soc., 2018, 140(30), 9400-9403.
[] [PMID: 30015479]
Kepski, K.; Rice, C.R.; Moran, W.J. Cyclic vinyl(aryl)iodonium salts: synthesis and reactivity. Org. Lett., 2019, 21, 6936-6939.
[] [PMID: 31452372]
Ochiai, M.; Kitagawa, Y.; Takayama, N.; Takaoka, Y.; Shiro, M. Synthesis of chiral diaryliodonium salts, 1,1′-binaphthyl-2-yl(phenyl)iodonium tetrafluoroborates: asymmetric α-phenylation of β-keto ester enolates. J. Am. Chem. Soc., 1999, 121, 9233-9234.
Jalalian, N.; Olofsson, B. Design and asymmetric synthesis of chiral diaryliodonium salts. Tetrahedron, 2010, 66, 5793-5800.
Murray, S.J.; Müller-Bunz, H.; Ibrahim, H. Congested C2-symmetric aryliodanes based on an anti-dimethanoanthracene backbone. Chem. Commun. (Camb.), 2012, 48(50), 6268-6270.
[] [PMID: 22609985]
Brown, M.; Delorme, M.; Malmedy, F.; Malmgren, J.; Olofsson, B.; Wirth, T. Synthesis of new chiral diaryliodonium salts. Synlett, 2015, 26, 1573-1577.

Rights & Permissions Print Export Cite as
© 2023 Bentham Science Publishers | Privacy Policy