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Electrocatalytic Carboxylation of Benzoyl Bromide with CO2 in Ionic Liquid 1-Butyl-3-Methyllimidazoliumtetrafluoborate to Methyl phenyl glyoxylate
Corresponding Author(s) : Guishan Tan
Asian Journal of Chemistry,
Vol. 26 No. 11 (2014): Vol 26 Issue 11
Abstract
A new electrochemical procedure for the electrocatalytic carboxylation of benzoyl bromide with CO2 in ionic liquid, 1-butyl-3-methyllimidazolium tetrafluoborate (BMIMBF4), to methyl phenyl glyoxylate was investigated. The experiments were carried out in three electrodes undivided cell under mild conditions and the use of volatile and toxic solvents and catalysts, as well as any other additional supporting electrolytes, was avoided. The electrochemical reduction behavior of benzoyl bromide in BMIMBF4 had been studied by cyclic voltammetry with a reduction peak at -1.6 V (vs. Ag). Methyl phenyl glyoxylate was obtained by typical electrolytic procedure.
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- L. Zhang, D.F. Niu, K. Zhang, G.R. Zhang, Y.W. Luo and J.X. Lu, Green Chem., 10, 202 (2008); doi:10.1039/b711981j.
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References
M. Aresta and A. Dibenedetto, Catal. Today, 98, 455 (2004); doi:10.1016/j.cattod.2004.09.001.
D.H. Gibson, Chem. Rev., 96, 2063 (1996); doi:10.1021/cr940212c.
A. Jutand, Chem. Rev., 108, 2300 (2008); doi:10.1021/cr068072h.
H. Kamekawa, H. Senboku and M. Tokuda, Electrochim. Acta, 42, 2117 (1997); doi:10.1016/S0013-4686(97)85488-6.
O. Scialdone, A. Galia, G. Errante, A.A. Isse, A. Gennaro and G. Filardo, Electrochim. Acta, 53, 2514 (2008); doi:10.1016/j.electacta.2007.10.021.
A.A. Isse and A. Gennaro, Chem. Commun., 4, 2798 (2002); doi:10.1039/b206746c.
S. Rondinini, P.R. Mussini, P. Muttini and G. Sello, Electrochim. Acta, 46, 3245 (2001); doi:10.1016/S0013-4686(01)00616-8.
O. Scialdone, A. Galia, A.A. Isse, A. Gennaro, M.A. Sabatino, R. Leone and G. Filardo, J. Electroanal. Chem., 609, 8 (2007); doi:10.1016/j.jelechem.2007.02.014.
O. Scialdone, M.A. Sabatino, C. Belfiore, A. Galia, M.P. Paternostro and G. Filardo, Electrochim. Acta, 51, 3500 (2006); doi:10.1016/j.electacta.2005.09.044.
M. Feroci, M. Orsini, L. Rossi, G. Sotgiu and A. Inesi, J. Org. Chem., 72, 200 (2007); doi:10.1021/jo061997c.
Z. Baan, Z. Finta, G. Keglevich and I. Hermecz, Green Chem., 11, 1937 (2009); doi:10.1039/b913305d.
L. Zhang, D.F. Niu, K. Zhang, G.R. Zhang, Y.W. Luo and J.X. Lu, Green Chem., 10, 202 (2008); doi:10.1039/b711981j.
R. Hagiwara and Y. Ito, J. Fluor. Chem., 105, 221 (2000); doi:10.1016/S0022-1139(99)00267-5.
L.E. Barrosse-Antle and R.G. Compton, Chem. Commun., 25, 3744 (2009); doi:10.1039/b906320j.
V.G. Koshechko, V.E. Titov and V.A. Lopushanskaya, Electrochem. Commun., 4, 655 (2002); doi:10.1016/S1388-2481(02)00409-5.
G.T. Cheek and P.A. Horine, J. Electrochem. Soc., 131, 1796 (1984); doi:10.1149/1.2115963.