Abstract
Most of the synthetic chemical transformation reactions involve the use of different organic solvents. Unfortunately, some of these toxic solvents are used in chemical laboratory, industry and have been considered a very serious problem for the health, safety of workers and environmental damage through pollution. The purpose of green chemistry is to provide a path that reduces or eliminates the use of such hazardous toxic solvents. Therefore, the key factor of the green synthetic approach is to utilize renewable materials, nontoxic chemical and to perform the reactions under solvent-free conditions. In this review, we have discussed most recent literature survey on applications of solvent-free techniques in organic synthesis which would offer a new opportunity to a researcher to overcome the problem of using environmental harmful solvents.
Keywords: Organic synthesis, solvent-free technique, solid-state reactions, green chemistry, mechanochemistry, microwave irradiation, ultrasound irradiation.
[http://dx.doi.org/10.1007/s00706-008-0061-y]
[http://dx.doi.org/10.2298/JSC110831001S]
[http://dx.doi.org/10.1080/15685551.2013.771316]
[http://dx.doi.org/10.1016/j.cclet.2013.07.022]
[http://dx.doi.org/10.1016/j.bmcl.2011.03.080] [PMID: 21507638]
[http://dx.doi.org/10.1016/j.apsusc.2005.11.006]
[http://dx.doi.org/10.1016/j.tetlet.2007.09.030]
[http://dx.doi.org/10.2174/1389557511313120009] [PMID: 22625410]
[http://dx.doi.org/10.2174/138955705774329564] [PMID: 16250831]
[http://dx.doi.org/10.1155/2011/984297]
[http://dx.doi.org/10.1007/s11172-005-0440-z]
[http://dx.doi.org/10.1002/jhet.3507]
[http://dx.doi.org/10.1021/bk-2000-0767]
[http://dx.doi.org/10.1021/ar010065m] [PMID: 12234198]
(b) Obst, M.; Konig, B. Organic synthesis without conventional solvents. Eur. J. Org. Chem., 2018, 31, 4213-4232. http://10.1002/ejoc.201800556
(c) Tavakolian, M.; Vahdati-khajeh, S.; Asgari, S. Recent advances in solvent-free asymmetric catalysis. ChemCatChem, 2019, 11, 2943-2977.
[http://dx.doi.org/10.1002/cctc.201900354]
[http://dx.doi.org/10.1039/a808223e]
[http://dx.doi.org/10.1021/cr940089p] [PMID: 11749257]
[http://dx.doi.org/10.1002/9780470988305]
[http://dx.doi.org/10.1021/ja0034388] [PMID: 11535074]
[http://dx.doi.org/10.1002/jccs.200900148]
[http://dx.doi.org/10.1021/jo00013a055]
[http://dx.doi.org/10.1039/c8ob01187g rsc.li/obc]
[http://dx.doi.org/10.1039/p19900003207]
[http://dx.doi.org/10.1039/a805884i]
[http://dx.doi.org/10.1081/SCC-120014780]
[http://dx.doi.org/10.1002/ange.19891010317]
[http://dx.doi.org/10.1039/b007431o]
[http://dx.doi.org/10.1021/jo00274a007]
[http://dx.doi.org/10.1016/S0223-5234(00)01189-2] [PMID: 11248403]
[http://dx.doi.org/10.1021/jm00001a017] [PMID: 7837222]
[http://dx.doi.org/10.1080/17518253.2010.487841]
[http://dx.doi.org/10.1080/00397910802664244]
[http://dx.doi.org/10.4172/2150-3494.1000011]
[http://dx.doi.org/10.1016/j.arabjc.2010.12.012.]
[http://dx.doi.org/10.1016/S0278-6915(99)00010-1] [PMID: 10418958]
[http://dx.doi.org/10.1039/C6RA22466K]
[http://dx.doi.org/10.1002/jccs.201200610]
[http://dx.doi.org/10.1021/jo981794r] [PMID: 11674183]
[http://dx.doi.org/10.1039/C7RA02177A]
[http://dx.doi.org/10.1016/S0040-4039(98)00206-8]
[http://dx.doi.org/10.1080/00397910601031553]
[http://dx.doi.org/10.1016/S0065-2725(08)60008-2]
[http://dx.doi.org/10.1039/C39880001202]
[http://dx.doi.org/10.1073/pnas.97.13.7124] [PMID: 10860979]
[http://dx.doi.org/10.1016/j.bmcl.2007.09.095] [PMID: 17933535]
[http://dx.doi.org/10.1016/j.ejmech.2009.04.017] [PMID: 19419801]
[http://dx.doi.org/10.1016/S0040-4020(01)01189-9]
[http://dx.doi.org/10.1080/00397911.2011.643438]
[http://dx.doi.org/10.1016/j.tetlet.2011.02.031]
[http://dx.doi.org/10.1080/00397910902796102]
[http://dx.doi.org/10.1080/00397911.2012.716484]
[http://dx.doi.org/10.3762/bjoc.15.7]
[http://dx.doi.org/10.1021/jo010586n] [PMID: 11722233]
[http://dx.doi.org/10.1016/S0040-4039(99)01000-X]
[http://dx.doi.org/10.1081/SCC-120013725]
[http://dx.doi.org/10.1081/SCC-200039461]
[http://dx.doi.org/10.1021/ja9713441]
[http://dx.doi.org/10.1021/ja983802r]
[http://dx.doi.org/10.1016/S0040-4039(01)02180-3]
[http://dx.doi.org/10.1002/anie.199422071]
[http://dx.doi.org/10.1002/1521-3765(20020104)8:1<94:AID-CHEM94>3.0.CO;2-L] [PMID: 11822467]
[http://dx.doi.org/10.1002/anie.199727791]
[http://dx.doi.org/10.1021/cm0103702]
[http://dx.doi.org/10.1021/ja036466+] [PMID: 12926952]
[http://dx.doi.org/10.1002/macp.1994.021950323]
[http://dx.doi.org/10.1080/15421400701432412]
[http://dx.doi.org/10.1016/j.bmcl.2007.12.043] [PMID: 18182288]
[http://dx.doi.org/10.1016/S0040-6090(00)00976-7]
[http://dx.doi.org/10.1023/A:1019513313773]
[http://dx.doi.org/10.1016/j.ejmech.2010.07.028] [PMID: 20696501]
[http://dx.doi.org/10.1016/j.bmc.2006.01.042] [PMID: 16460945]
[http://dx.doi.org/10.1002/ardp.201100077] [PMID: 21755528]
[http://dx.doi.org/10.1002/ardp.201100170]
[http://dx.doi.org/10.1016/j.ejmech.2007.11.005] [PMID: 18187238]
[http://dx.doi.org/10.1016/j.bmcl.2010.03.083] [PMID: 20385494]
[http://dx.doi.org/10.1016/j.bmcl.2004.06.046] [PMID: 15357972]
[http://dx.doi.org/10.1016/j.bmcl.2005.03.121] [PMID: 15893928]
[http://dx.doi.org/10.1080/00397911.2010.531492]
[http://dx.doi.org/10.1590/S0103-50532009000200023]
[http://dx.doi.org/10.1002/chin.200750139]
[http://dx.doi.org/10.1080/17518253.2012.713123]
[http://dx.doi.org/10.1039/C0GC00830C]
[http://dx.doi.org/10.1007/s002280050706] [PMID: 10805063]
[PMID: 9808096]
[http://dx.doi.org/10.1002/jlac.18822150102]
[http://dx.doi.org/10.1021/jo951706s]
[http://dx.doi.org/10.1016/j.tet.2004.11.079]
[http://dx.doi.org/10.1016/S0040-4039(03)00813-X]
[http://dx.doi.org/10.1248/cpb.56.1002] [PMID: 18591819]
[http://dx.doi.org/10.1016/j.tetlet.2004.10.057]
[http://dx.doi.org/10.1016/j.tet.2005.01.008]
[http://dx.doi.org/10.1021/cc0600425] [PMID: 17096571]
[http://dx.doi.org/10.1016/j.tet.2007.11.008]
[http://dx.doi.org/10.1007/978-1-4615-3822-6]
[http://dx.doi.org/10.1038/382522a0]
[http://dx.doi.org/10.1080/713935610]
[http://dx.doi.org/10.1016/j.optmat.2008.01.003]
[http://dx.doi.org/10.1039/b211421f] [PMID: 12669843]
[http://dx.doi.org/10.1081/SCC-120016343]
[http://dx.doi.org/10.1016/j.dyepig.2005.12.002]
[http://dx.doi.org/10.1016/j.dyepig.2008.10.011]
[http://dx.doi.org/10.1080/17518253.2014.969786]
[http://dx.doi.org/10.1016/S0960-894X(01)00102-0] [PMID: 11294390]
[http://dx.doi.org/10.1074/jbc.M402110200] [PMID: 15123603]
[http://dx.doi.org/10.1002/prac.19803220414]
[http://dx.doi.org/10.1016/S0960-894X(01)80574-6]
[http://dx.doi.org/10.1021/jm00117a010] [PMID: 2970549]
[http://dx.doi.org/10.1021/jm00025a010] [PMID: 8523406]
[http://dx.doi.org/10.1021/jm00092a006] [PMID: 1635057]
[http://dx.doi.org/10.1021/jm00362a014] [PMID: 6876084]
[http://dx.doi.org/10.1080/00397911003629440]
[http://dx.doi.org/10.1021/ar000106z] [PMID: 11513568]
[http://dx.doi.org/10.1021/ja00090a031]
[http://dx.doi.org/10.1016/S0379-6779(98)00091-5]
[http://dx.doi.org/10.1002/adma.19960080609]
[http://dx.doi.org/10.1002/anie.199009771]
[http://dx.doi.org/10.1002/3527607439]
[http://dx.doi.org/10.1039/97818475506020]
[http://dx.doi.org/10.1021/jm000164q] [PMID: 10978192]
[http://dx.doi.org/10.1016/S0040-4039(99)00945-4]
[http://dx.doi.org/10.1080/00397910701860596]
[http://dx.doi.org/10.1081/SCC-120028355]
[http://dx.doi.org/10.1016/S0040-4039(00)93564-0]
[http://dx.doi.org/10.1039/p19930000739]
[http://dx.doi.org/10.1016/S0040-4020(01)89986-5]
[http://dx.doi.org/10.1002/adsc.200700252]
[http://dx.doi.org/10.1039/b706167f]
[http://dx.doi.org/10.1016/j.tet.2008.08.047]
[http://dx.doi.org/10.1039/b915669k]
[http://dx.doi.org/10.1021/op800148y]
[http://dx.doi.org/10.1039/c000674b]
[http://dx.doi.org/10.1002/cssc.201000122] [PMID: 20737534]
[http://dx.doi.org/10.1080/00397911.2011.599103]
[http://dx.doi.org/10.1080/00397910902898551]
[http://dx.doi.org/10.1016/S0040-4020(97)00476-6]
[http://dx.doi.org/10.1039/a707613d] [PMID: 11072891]
[http://dx.doi.org/10.1016/S0960-894X(98)00495-8] [PMID: 9873604]
[http://dx.doi.org/10.1016/S0014-4886(03)00268-1] [PMID: 14552867]
[http://dx.doi.org/10.1016/j.molmed.2004.01.007] [PMID: 15102355]
[http://dx.doi.org/10.1002/jcp.20169] [PMID: 15316926]
[PMID: 14582449]
[http://dx.doi.org/10.1021/jm049121q] [PMID: 15857149]
[http://dx.doi.org/10.1021/jm00020a002] [PMID: 7562922]
[http://dx.doi.org/10.2174/1389557043403756] [PMID: 15279594]
[http://dx.doi.org/10.2174/13852728113179990040]
[http://dx.doi.org/10.1021/acs.orglett.6b02325] [PMID: 27623160]
[http://dx.doi.org/10.2174/157017907781369289]
[http://dx.doi.org/10.1016/j.tet.2016.09.015]
(b) Lofstrand, V.A.; Matsuura, B.S.; Furst, L.; Narayanam, J.M.R.; Stephenson, C.R.J. Formation and trapping of azafulvene intermediates derived from manganese-mediated oxidative malonate coupling. Tetrahedron, 2016, 72(26), 3775-3780.
[http://dx.doi.org/10.1016/j.tet.2016.03.012] [PMID: 27551160]
(c) Li, L.; Wang, J-J.; Wang, G-W. Manganese (III) acetate-promoted cross-coupling reaction of benzothiazole/thiazole derivatives with organophosphorus compounds under ball-milling conditions. J. Org. Chem., 2016, 81(13), 5433-5439.
[http://dx.doi.org/10.1021/acs.joc.6b00786] [PMID: 27248000]
(d) Zhang, G-Y.; Li, C-K.; Li, D-P.; Zeng, R-S.; Shoberu, A.; Zou, J-P. Solvent-controlled direct radical oxyphosphorylation of styrenes mediated by Manganese (III). Tetrahedron, 2016, 72, 2972-2978.
[http://dx.doi.org/10.1016/j.tet.2016.04.013]
(e) Chuang, C-P.; Chen, Y-J. Manganese (III) acetate mediated oxidative radical cyclizations of α-substituted N-[2-(phenylethynyl)phenyl] acetamides. Tetrahedron, 2016, 72, 1911-1918.
[http://dx.doi.org/10.1016/j.tet.2016.02.041]
[http://dx.doi.org/10.1039/c3cs35526h] [PMID: 23660585]
[http://dx.doi.org/10.1021/jacs.6b00097] [PMID: 26895404]
[http://dx.doi.org/10.1016/j.tet.2014.05.039]
[http://dx.doi.org/10.1016/j.tetlet.2017.01.016]
[http://dx.doi.org/10.1021/cr00094a007]
[http://dx.doi.org/10.1016/j.tetlet.2010.09.069]
[http://dx.doi.org/10.1016/j.tetlet.2003.09.077]
[http://dx.doi.org/10.1021/jo00022a002]
(b) Larock, R.C.; Yum, E.K. Synthesis of indoles via palladium catalysed hetero annulations of internal alkynes. J. Am. Chem. Soc., 1991, 113, 6689-6690.
[http://dx.doi.org/10.1021/ja00017a059]
(c) Busacca, C.A.; Johnson, R.E. Synthesis of novel tetrahydrobenzazepinones. Tetrahedron Lett., 1992, 33, 165-168.
[http://dx.doi.org/10.1016/0040-4039(92)88040-C]
(d) Swenton, J.S.; Callinan, A.; Wang, S. Efficient synthesis of vinyl ethers of spiro quinol ketals and their high yield photochemical oxygen to carbon [1,3]-shift to spiro-fused 2,5-cycohexadienanes. J. Org. Chem., 1992, 57, 78-85.
[http://dx.doi.org/10.1021/jo00027a017]
[http://dx.doi.org/10.1016/S0022-1139(01)00378-5]
[http://dx.doi.org/10.1021/cr0102967] [PMID: 12428984]
(b) Nicolaou, K.C. The battle of calicheamic- in1. Angew. Chem. Int. Ed. Engl., 1993, 32, 1377.
[http://dx.doi.org/10.1021/cr60135a004] [PMID: 18887958]
[http://dx.doi.org/10.1021/jo00121a064]
[http://dx.doi.org/10.1055/s-1999-2818]
[http://dx.doi.org/10.1021/ja0465247] [PMID: 15571400]
[http://dx.doi.org/10.3184/030823406776330657]
[http://dx.doi.org/10.1080/00397910802594268]
[http://dx.doi.org/10.1016/0040-4039(96)00738-1]
[http://dx.doi.org/10.1021/ol9029337] [PMID: 20184339]
[http://dx.doi.org/10.1021/jo00063a052]
[http://dx.doi.org/10.1021/ol100587j] [PMID: 20387852]
[http://dx.doi.org/10.1002/adsc.201300581]
[http://dx.doi.org/10.1016/j.tetlet.2014.02.064]
[http://dx.doi.org/10.1351/pac200678050935]
[http://dx.doi.org/10.1073/pnas.0601687103] [PMID: 16754869]
[http://dx.doi.org/10.1021/cr068006f] [PMID: 17973536]
[http://dx.doi.org/10.1021/ar800164n] [PMID: 19220064]
[http://dx.doi.org/10.1002/asia.200900487] [PMID: 20041458]
[http://dx.doi.org/10.1007/128_2009_17] [PMID: 21500410]
[http://dx.doi.org/10.1021/cr100280d] [PMID: 21391561]
[http://dx.doi.org/10.1039/c1cs15082k] [PMID: 21643614]
[http://dx.doi.org/10.1021/cr100198w] [PMID: 21049955]
[http://dx.doi.org/10.1039/c2cs15323h] [PMID: 22349590]
[http://dx.doi.org/10.1021/jo2015533] [PMID: 21961457]
[http://dx.doi.org/10.1039/b816788e]
[http://dx.doi.org/10.1016/j.tetlet.2013.02.007]
[http://dx.doi.org/10.1038/421571a] [PMID: 12571563]
[http://dx.doi.org/10.1016/S0040-4039(00)83996-9]
[http://dx.doi.org/10.1016/S0040-4039(00)85103-5]
[http://dx.doi.org/10.1080/10426500307933]
[http://dx.doi.org/10.1002/jccs.200300172]
[http://dx.doi.org/10.1016/j.bmc.2007.08.021] [PMID: 17804244]
[http://dx.doi.org/10.1016/j.bmcl.2006.08.017] [PMID: 16908145]
[http://dx.doi.org/10.1016/j.freeradbiomed.2011.09.032] [PMID: 22036835]
[http://dx.doi.org/10.1590/S0103-50532011000700014]
[http://dx.doi.org/10.3390/molecules14072431] [PMID: 19633614]
[http://dx.doi.org/10.1021/jm4001117] [PMID: 23547728]
[http://dx.doi.org/10.1021/ol403456b] [PMID: 24428260]
[http://dx.doi.org/10.1016/j.ejmech.2012.03.049] [PMID: 22658085]
[http://dx.doi.org/10.1016/j.molstruc.2005.10.004]
[http://dx.doi.org/10.1080/10426500802388433]
[http://dx.doi.org/10.1007/s11172-012-0108-4]
[http://dx.doi.org/10.1111/j.1368-5031.2004.00167.x] [PMID: 15311563]
[http://dx.doi.org/10.1358/dot.2001.37.2.614849] [PMID: 12783104]
[http://dx.doi.org/10.1016/j.ejmech.2008.02.047] [PMID: 18486994]
[http://dx.doi.org/10.1002/prot.21837] [PMID: 18041758]
[http://dx.doi.org/10.1016/S0040-4039(99)00620-6]
[http://dx.doi.org/10.1016/S0040-4039(00)00771-1]
[http://dx.doi.org/10.2174/157017811799304296]
[http://dx.doi.org/10.1055/s-1996-5587]
[http://dx.doi.org/10.1016/S0040-4039(00)73662-8]
[http://dx.doi.org/10.1016/S0040-4039(97)00262-1]
[http://dx.doi.org/10.1016/S0040-4039(97)10093-4]
[http://dx.doi.org/10.1016/S0040-4039(00)95286-9]
[http://dx.doi.org/10.1055/s-1995-5236]
[http://dx.doi.org/10.1081/SCC-120037921]
[http://dx.doi.org/10.1080/00397919008051553]
[http://dx.doi.org/10.1080/00397919708006036]
[http://dx.doi.org/10.1081/SCC-120004081]
[http://dx.doi.org/10.1080/00397919908086090]
[http://dx.doi.org/10.1039/p19930000999]
[http://dx.doi.org/10.1039/B101375K]
[http://dx.doi.org/10.1016/S0040-4039(00)93370-7]
[http://dx.doi.org/10.1016/S0040-4039(00)60635-4]
[http://dx.doi.org/10.1080/00397919908086108]
[http://dx.doi.org/10.1016/j.tetlet.2008.09.166]
[http://dx.doi.org/10.1016/S0040-4039(97)01213-6]
[http://dx.doi.org/10.1016/S0040-4039(97)00261-X]
[http://dx.doi.org/10.1055/s-1997-5771]
[http://dx.doi.org/10.1007/s007830050061]
[http://dx.doi.org/10.1016/S0040-4039(97)10521-4]
[http://dx.doi.org/10.1016/S0040-4039(97)00968-4]
[http://dx.doi.org/10.1016/S0040-4039(97)10763-8]
[http://dx.doi.org/10.1016/S0040-4039(98)00010-0]
[http://dx.doi.org/10.1007/s007830050059]
[http://dx.doi.org/10.1016/S0040-4039(99)01585-3]
[http://dx.doi.org/10.1016/S0040-4039(97)01660-2]
[http://dx.doi.org/10.1016/S0040-4039(98)01922-4]
[http://dx.doi.org/10.1080/17518250701756991]
[http://dx.doi.org/10.1070/RC2002v071n11ABEH000763]
[http://dx.doi.org/10.1016/S0040-4020(97)00640-6]
[http://dx.doi.org/10.1080/10587259408037780]
[http://dx.doi.org/10.1081/SCC-120027269]
[http://dx.doi.org/10.1023/A:1023060030558] [PMID: 12882156]
[http://dx.doi.org/10.1016/j.jasms.2005.01.012] [PMID: 15792728]
[http://dx.doi.org/10.1021/jo960309u] [PMID: 11667729]
[http://dx.doi.org/10.1016/S0040-4039(98)00765-5]
[http://dx.doi.org/10.1016/j.molcatb.2008.08.006]
[http://dx.doi.org/10.1039/b617544a] [PMID: 17377658]
[http://dx.doi.org/10.1039/B401145G] [PMID: 15034633]
[http://dx.doi.org/10.1002/marc.200800690] [PMID: 21706603]
[http://dx.doi.org/10.1021/cr0002590] [PMID: 11710242]
[http://dx.doi.org/10.1039/b608891k]
[http://dx.doi.org/10.1016/j.eurpolymj.2004.05.007]
[http://dx.doi.org/10.1080/17518253.2010.501429]
[http://dx.doi.org/10.1080/00397911.2018.1434894]
[http://dx.doi.org/10.2174/13852728113179990018]
[http://dx.doi.org/10.1016/j.ultsonch.2009.02.005] [PMID: 19324584]
[http://dx.doi.org/10.1186/1860-5397-3-13] [PMID: 17374170]
[http://dx.doi.org/10.1080/00397911.2012.718026]
[http://dx.doi.org/10.1002/cjoc.200990238]
[http://dx.doi.org/10.1007/BF03246215]