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Letters in Organic Chemistry

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ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

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Letter Article

Dual Functionality of Choline Hydroxide for the Dakin Reaction

Author(s): Seong-Ryu Joo and Seung-Hoi Kim*

Volume 19, Issue 5, 2022

Published on: 02 February, 2021

Page: [341 - 346] Pages: 6

DOI: 10.2174/1570178618666210202155412

Price: $65

Abstract

A facile synthetic approach to Dakin oxidation utilizing green conditions was demonstrated. A combination of hydrogen peroxide and aqueous choline hydroxide in cooperation with various hydroxyl aryl aldehydes and ketones was used to provide the corresponding dihydric aromatic compounds. The whole procedure was conducted at ambient temperature in an aerobic environment. The scope of ChOH/H2O2 platform was also investigated, showing that the reactivity of the present platform was highly dependent on the position of the hydroxy group of the aromatic ring.

Keywords: Dakin oxidation, room-temperature ionic liquid, choline hydroxide, hydrogen peroxide, dihydric, aerobic condition.

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[1]
Dakin, H.D. Am. Chem. J., 1909, 62, 477-498.
[2]
Dakin, H.D.; Clarke, H.T.; Taylor, E.R. Organic Syntheses Collective, 1941, 1, 149-152.
[3]
Dakin, H.D. Org. Synth., 1933, 149-154.
[4]
Abe, T.; Itoh, T.; Choshi, T.; Hibino, S.; Ishikura, M. Tetrahedron Lett., 2014, 55, 5268-5270.
[http://dx.doi.org/10.1016/j.tetlet.2014.07.113]
[5]
Jung, M.E.; Lazarova, T.I. J. Org. Chem., 1997, 62, 1553-1555.
[http://dx.doi.org/10.1021/jo962099r]
[6]
Faure, E.; Falentin-Daudré, C.; Jérôme, C.; Lyskawa, J.; Fournier, D.; Woisel, P.; Detrembleur, C. Prog. Polym. Sci., 2013, 38, 236-270.
[http://dx.doi.org/10.1016/j.progpolymsci.2012.06.004]
[7]
Fache, M.; Darroman, E.; Besse, V.; Auvergne, R.; Caillol, S.; Boutevin, B. Green Chem., 2014, 16, 1987-1998.
[http://dx.doi.org/10.1039/C3GC42613K]
[8]
Fache, M.; Boutevin, B.; Caillol, S. Green Chem., 2016, 18, 712-725.
[http://dx.doi.org/10.1039/C5GC01070E]
[9]
Yaremenko, I.A.; Viľ, V.A.; Demchuk, D.V.; Terenťev, A.O. Beilstein J. Org. Chem., 2016, 12, 1674.
[http://dx.doi.org/10.3762/bjoc.12.162]
[10]
Wang, Z.; Chen, X.; Wang, C.; Zhang, L.; Li, F.; Zhang, W.; Chen, P.; Wang, L. Green Chem. Lett. Rev., 2017, 10, 269-273.
[http://dx.doi.org/10.1080/17518253.2017.1375159]
[11]
Chen, S.; Hossain, M.S.; Foss, F.W., Jr Org. Lett., 2012, 14(11), 2806-2809.
[http://dx.doi.org/10.1021/ol3010326] [PMID: 22587606]
[12]
Chen, S.; Foss, F.W., Jr Org. Lett., 2012, 14(19), 5150-5153.
[http://dx.doi.org/10.1021/ol302479b] [PMID: 23016963]
[13]
Sarmah, M.; Mondal, M.; Bora, U. Chem. Select, 2017, 2, 5180.
[http://dx.doi.org/10.1002/slct.201700580]
[14]
Saikia, B.; Borah, P. RSC Advances, 2015, 5, 10558.
[15]
Saikia, B.; Borah, P.; Barua, N.C. Green Chem., 2015, 17, 4523.
[http://dx.doi.org/10.1039/C5GC01404B]
[16]
Varma, R.S.; Naicker, K.P. Org. Lett., 1999, 1, 189.
[http://dx.doi.org/10.1021/ol990522n]
[17]
Kabalka, G.W.; Reddy, N.K.; Narayana, C. Tetrahedron Lett., 1992, 33, 865-866.
[http://dx.doi.org/10.1016/S0040-4039(00)91561-2]
[18]
Roy, A.; Reddy, K.R.; Mohanta, P.K.; Ila, H.; Junjappa, H. Synth. Commun., 1999, 29, 3781.
[http://dx.doi.org/10.1080/00397919908086017]
[19]
Zambrano, J.L.; Dorta, R. Synlett, 2003, 10, 1545-1546.
[http://dx.doi.org/10.1055/s-2003-40848]
[20]
da Silva, E.T.; Camara, C.A.; Antunes, O.A.C.; Barreiro, E.J.; Fraga, C.A.M. Synth. Commun., 2008, 38, 784.
[http://dx.doi.org/10.1080/00397910701820673]
[21]
Vekariya, R.L. J. Mol. Liq., 2017, 227, 44.
[http://dx.doi.org/10.1016/j.molliq.2016.11.123]
[22]
Bernini, R.; Coratti, A.; Provenzano, G.; Fabrizi, G.; Tofani, D. Tetrahedron, 2005, 61, 1821.
[http://dx.doi.org/10.1016/j.tet.2004.12.025]
[23]
Shin, E-J.; Kwon, G-T.; Kim, S-H. Synlett, 2019, 30, 1815.
[http://dx.doi.org/10.1055/s-0037-1611894]
[24]
Joo, S-R.; Kwon, G-T.; Kim, S-H. Asian J. Org. Chem., 2020, 9, 584.
[http://dx.doi.org/10.1002/ajoc.202000059]
[25]
Hocking, M.B.; Ong, J.H. Can. J. Chem., 1977, 55, 102.
[http://dx.doi.org/10.1139/v77-019]
[26]
Hocking, M.B.; Bhandari, K.; Shell, B.; Smyth, T.A. J. Org. Chem., 1982, 47, 4208.
[http://dx.doi.org/10.1021/jo00143a007]
[27]
Gohain, M.; du Plessis, M.; van Tonder, J.H.; Bezuidenhoudt, B.C.B. Tetrahedron Lett., 2014, 55, 2082.
[http://dx.doi.org/10.1016/j.tetlet.2014.02.048]

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