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Current Organocatalysis

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ISSN (Print): 2213-3372
ISSN (Online): 2213-3380

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Mini-Review Article

Indium Metal-Mediated Reactions in Water: Diverse Synthesis of Important Organic Compounds

Author(s): Monika Kamboj*, Sangeeta Bajpai, Garima Pandey and Bimal Krishna Banik*

Volume 10, Issue 2, 2023

Published on: 12 May, 2023

Page: [74 - 80] Pages: 7

DOI: 10.2174/2213337210666230331115645

Price: $65

Abstract

Ecofriendly Indium catalyzed synthesis of organic compounds finds various applications in health sectors, electronics, semiconductors, and many more. An efficient co-catalyst and oriented catalyst behavior of Indium has become a choice for many organic transformations. Its compatibility with water, showing nontoxic and nonreactive action, proceeds the reactions with ease. Focus on Indium metal-mediated important organic transformations in water, is visible during the last decades, resulting in diverse organic compounds with excellent yields This present mini-review highlights some important indium metal-mediated reactions in water, for the diverse synthesis of important organic compounds.

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[1]
Yadav, J.S.; Antony, A.; George, J.; Subba Reddy, B.V. Recent developments in indium metal and its salts in organic synthesis. Eur. J. Org. Chem., 2010, 2010(4), 591-605.
[http://dx.doi.org/10.1002/ejoc.200900895]
[2]
Dagorne, S.; Wehmschulte, R. Recent developments on the use of group 13 metal complexes in catalysis. Chem. Cat. Chem., 2018, 10(12), 2509-2520.
[http://dx.doi.org/10.1002/cctc.201800045]
[3]
Brandão, P.; Burke, A.J.; Pineiro, M. A decade of indium-catalyzed multicomponent reactions (MCRs). Eur. J. Org. Chem., 2020, 2020(34), 5501-5513.
[http://dx.doi.org/10.1002/ejoc.202000596]
[4]
Zhengyin, D.; Yanchun, Li. Indium reagent mediated reactions in aqueous media and their applications in organic synthesis. Huaxue Jinzhan, 2010, 22(1), 71-80.
[5]
Zhan, W.; Guo, Y.; Gong, X.; Guo, Y.; Wang, Y.; Lu, G. Current status and perspectives of rare earth catalytic materials and catalysis. Chin. J. Catal., 2014, 35(8), 1238-1250.
[http://dx.doi.org/10.1016/S1872-2067(14)60189-3]
[6]
Pae, A.; Cho, Y. Indium-mediated organic reactions in aqueous media. Curr. Org. Chem., 2002, 6(8), 715-737.
[http://dx.doi.org/10.2174/1385272023374030]
[7]
Welton, T. Solvents and sustainable chemistry. Proc.- Royal Soc., Math. Phys. Eng. Sci., 2015, 471(2183), 20150502.
[http://dx.doi.org/10.1098/rspa.2015.0502] [PMID: 26730217]
[8]
Francos, J.; Borge, J.; Díez, J.; García-Garrido, S.E.; Cadierno, V. Easy entry to donor/acceptor butadiene dyes through a MW-assisted InCl3-catalyzed coupling of propargylic alcohols with indan-1,3-dione in water. Catal. Commun., 2015, 63, 10-14.
[http://dx.doi.org/10.1016/j.catcom.2014.07.028]
[9]
Li, B.; Wang, G.; Li, Z.; Meng, X. InCl3-catalyzed synthesis of C-pyrrolyl glycosides via tandem condensation of aminosugars and 1,3-dicarbonyl compounds in water. Tetrahedron Lett., 2011, 52(30), 3891-3894.
[http://dx.doi.org/10.1016/j.tetlet.2011.05.083]
[10]
Urinda, S.; Kundu, D.; Majee, A.; Hajra, A. Indium triflate-catalyzed one-pot synthesis of 14-alkyl or aryl-14 H -dibenzo[ a, j]xanthenes in water. Heteroatom Chem., 2009, 20(4), 232-234.
[http://dx.doi.org/10.1002/hc.20539]
[11]
Wu, L.; Jiang, R.; Yang, J.M.; Wang, S.Y.; Ji, S.J. In(OTf)3 catalyzed C3-benzylation of indoles with benzyl alcohols in water. RSC Advances, 2013, 3(16), 5459-5464.
[http://dx.doi.org/10.1039/c3ra40251g]
[12]
Ranu, B.C.; Bhadra, S.; Adak, L. Indium(III) chloride-catalyzed oxidative cleavage of carbon–carbon multiple bonds by tert-butyl hydroperoxide in water—a safer alternative to ozonolysis. Tetrahedron Lett., 2008, 49(16), 2588-2591.
[http://dx.doi.org/10.1016/j.tetlet.2008.02.089]
[13]
Choppin, S.; Ferreiro-Medeiros, L.; Barbarotto, M.; Colobert, F. Recent advances in the diastereoselective Reformatsky-type reaction. Chem. Soc. Rev., 2013, 42(3), 937-949.
[http://dx.doi.org/10.1039/C2CS35351B] [PMID: 23212078]
[14]
Moslin, R.M.; Jamison, T.F. Highly convergent total synthesis of (+)-acutiphycin. J. Am. Chem. Soc., 2006, 128(47), 15106-15107.
[http://dx.doi.org/10.1021/ja0670660] [PMID: 17117859]
[15]
Wessjohann, L.A.; Scheid, G.O.; Eichelberger, U.; Umbreen, S. Total synthesis of epothilone D: the nerol/macroaldolization approach. J. Org. Chem., 2013, 78(21), 10588-10595.
[http://dx.doi.org/10.1021/jo401355r] [PMID: 24079664]
[16]
Lambert, T.H.; Danishefsky, S.J. Total Synthesis of UCS1025A. J. Am. Chem. Soc., 2006, 128(2), 426-427.
[http://dx.doi.org/10.1021/ja0574567] [PMID: 16402826]
[17]
Grellepois, F. Enantiopure trifluoromethylated β(3,3)-amino acids: Synthesis by asymmetric Reformatsky reaction with stable analogues of trifluoromethyl N-tert-butanesulfinylketoimines and incorporation into α/β-peptides. J. Org. Chem., 2013, 78(3), 1127-1137.
[http://dx.doi.org/10.1021/jo302549v] [PMID: 23273379]
[18]
Chan, T-H.; Li, C-J.; Lee, M-C.; Wei, Z-Y. Organometallic-type reactions in aqueous media - a new challenge in organic synthesis. J. Chem., 1994, 72, 1181-1192.
[19]
Chao, L.C.; Rieke, R.D. Activated metals. IX. New reformatsky reagent involving activated indium for the preparation of. beta.-hydroxy esters. J. Org. Chem., 1975, 40(15), 2253-2255.
[http://dx.doi.org/10.1021/jo00903a031]
[20]
Huang, J.; Wu, F.; Li, Z.; Ni, Z.; Sun, R.; Nie, H.; Tang, H.; Song, L. Indium-mediated reformatsky reaction of iododifluoro ketones with aldehydes: Preparation of αα-difluoro-β-hydroxyketone derivatives in water. Syn. Open, 2022, 6(1), 19-30.
[http://dx.doi.org/10.1055/s-0040-1719888]
[21]
Nishikawa, Y.; Ohtsuka, Y.; Ogihara, H.; Rattanawan, R.; Gao, M.; Nakayama, A.; Hasegawa, J.; Yamanaka, I. Catalytic mechanism of liquid-metal indium for direct dehydrogenative conversion of methane to higher hydrocarbons. ACS Omega, 2020, 5(43), 28158-28167.
[http://dx.doi.org/10.1021/acsomega.0c03827] [PMID: 33163798]
[22]
Du, Z.; Wang, F.; Zhou, W.; Wang, J.X. Indium-mediated barbier-type allylation reaction in PEG400 and PEG400/H2O. J. Chem. Res., 2010, 34(8), 475-477.
[http://dx.doi.org/10.3184/030823410X12813608471242]
[23]
Abrego, D.; Bandyopadhyay, D.; Banik, B.K. Microwave-induced indium-catalyzed synthesis of pyrrole fused with indoline in water. Heterocycl Lett., 2011, 1(2), 94-95.
[24]
Patel, R.V.; Patel, J.K.; Nile, S.H.; Park, S.W. Synthesis and biological evaluation of piperazinyl-2-(Benzo)thiophen/-furan-2-yl-acetonitriles as strecker reaction products. Lett. Drug Des. Discov., 2013, 10(5), 462-470.
[http://dx.doi.org/10.2174/1570180811310050014]
[25]
Reinares-Fisac, D.; Aguirre-Díaz, L.M.; Iglesias, M.; Snejko, N.; Gutiérrez-Puebla, E.; Monge, M.Á.; Gándara, F. A mesoporous indium metal–organic framework: remarkable advances in catalytic activity for strecker reaction of ketones. J. Am. Chem. Soc., 2016, 138(29), 9089-9092.
[http://dx.doi.org/10.1021/jacs.6b05706] [PMID: 27420904]
[26]
Cañete, Á.; Salas, C.; Zacconi, F. Efficient indium-mediated dehalogenation of aromatics in ionic liquid media. Molecules, 2012, 18(1), 398-407.
[http://dx.doi.org/10.3390/molecules18010398] [PMID: 23275048]
[27]
Bandyopadhyay, D.; Mukherjee, S.; Banik, B. A selective, expeditious and sustainable entry en route to benzopyrazines and bis-benzopyrazines. Comb. Chem. High Throughput Screen., 2015, 18(1), 53-62.
[http://dx.doi.org/10.2174/1386207318666150131125053] [PMID: 25643327]
[28]
Kranjc, K.; Kocevar, M. Microwave-assisted organic synthesis: General considerations and transformations of heterocyclic compounds. Curr. Org. Chem., 2010, 14(10), 1050-1074.
[http://dx.doi.org/10.2174/138527210791130488]
[29]
Matassini, C.; Bonanni, M.; Marradi, M.; Cicchi, S.; Goti, A. On the virtue of indium in reduction reactions. A comparison of reductions mediated by indium and zinc: Is indium metal an effective catalyst for zinc induced reductions? Eur. J. Inorg. Chem., 2020, 2020(11-12), 1106-1113.
[http://dx.doi.org/10.1002/ejic.201901081]
[30]
Cotton, F.A.; Wilkinson, G. Advanced Inorganic Chemistry: A Comprehensive Text, 4th ed.; A Wiley-Interscience Publication, John Wiley & Son Inc: New York, 1980.
[31]
Guo, W.; Tan, X.; Bi, J.; Xu, L.; Yang, D.; Chen, C.; Zhu, Q.; Ma, J.; Tayal, A.; Ma, J.; Huang, Y.; Sun, X.; Liu, S.; Han, B. Atomic indium catalysts for switching CO2 electroreduction products from formate to CO. J. Am. Chem. Soc., 2021, 143(18), 6877-6885.
[http://dx.doi.org/10.1021/jacs.1c00151] [PMID: 33856799]
[32]
Zha, B.; Li, C.; Li, J. Efficient electrochemical reduction of CO2 into formate and acetate in polyoxometalate catholyte with indium catalyst. J. Catal., 2020, 382, 69-76.
[http://dx.doi.org/10.1016/j.jcat.2019.12.010]
[33]
Lin, M.H.; Tsai, W.S.; Lin, L.Z.; Hung, S.F.; Chuang, T.H.; Su, Y.J. Methods for the preparation of allenes employing indium- and zinc-mediated dehalogenation reactions in aqueous solutions. J. Org. Chem., 2011, 76(20), 8518-8523.
[http://dx.doi.org/10.1021/jo2015104] [PMID: 21895004]
[34]
Hou, Y.; Hu, J.; Xu, R.; Pan, S.; Zeng, X.; Zhong, G. Indium-mediated synthesis of benzylic hydroperoxides. Org. Lett., 2019, 21(12), 4428-4432.
[http://dx.doi.org/10.1021/acs.orglett.9b01070] [PMID: 31184170]
[35]
Takagi, T.; Kanamori, T. Indium-mediated radical addition of perfluoroalkyl iodide in water. J. Fluor. Chem., 2011, 132(6), 427-429.
[http://dx.doi.org/10.1016/j.jfluchem.2011.03.001]
[36]
Feng, Y.; Ma, W.; Yang, M.; Zhang, G.; Yu, Y.; Li, H.; Yang, Y. Green and efficient synthesis of chiral amines and hydroxylamines by indium (zinc)-copper-mediated alkylation reaction in aqueous media. Tetrahedron, 2022, 123, 132965.
[http://dx.doi.org/10.1016/j.tet.2022.132965]
[37]
Hou, S.L.; Dong, J.; Jiao, Z.H.; Jiang, X.L.; Yang, X.P.; Zhao, B. Trace water accelerating the CO 2 cycloaddition reaction catalyzed by an indium–organic framework. Inorg. Chem. Front., 2018, 5(7), 1694-1699.
[http://dx.doi.org/10.1039/C8QI00260F]
[38]
Onyestyák, G.; Harnos, S.; Kalló, D. In Indium: Properties; Technological Applications and Health Issues Nova Publishers: New York, 2013, pp. 53-81.
[39]
Schneider, U.; Kobayashi, S. Low-oxidation state indium-catalyzed C-C bond formation. Acc. Chem. Res., 2012, 45(8), 1331-1344.
[http://dx.doi.org/10.1021/ar300008t] [PMID: 22626010]

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