Preparation of Arylmercapturic Acids by S-Arylation of N,N′-Diacetylcystine
Jan Krouželka
Department of Organic Chemistry, Faculty of Chemical Technology, Institute of Chemical Technology Prague, Technická 1905, 166 28 Prague, Czech Republic, Fax: +420-220-444-288
Search for more papers by this authorIgor Linhart
Department of Organic Chemistry, Faculty of Chemical Technology, Institute of Chemical Technology Prague, Technická 1905, 166 28 Prague, Czech Republic, Fax: +420-220-444-288
Search for more papers by this authorJan Krouželka
Department of Organic Chemistry, Faculty of Chemical Technology, Institute of Chemical Technology Prague, Technická 1905, 166 28 Prague, Czech Republic, Fax: +420-220-444-288
Search for more papers by this authorIgor Linhart
Department of Organic Chemistry, Faculty of Chemical Technology, Institute of Chemical Technology Prague, Technická 1905, 166 28 Prague, Czech Republic, Fax: +420-220-444-288
Search for more papers by this authorGraphical Abstract
N,N′-Diacetylcystine dimethyl ester has been arylated at both sulfur atoms witharylboronic acids in the presence of CuI or CuII complexes under modified Chan–Lam–Evans coupling conditions to yield arylmercapturic acids.
Abstract
A simple convenient method has been developed for the preparation of N-acetyl-S-arylcysteines based on the Chan–Lam–Evans arylation of N,N′-diacetylcystine dimethyl ester with arylboronic acids and used to synthesize a series of arylmercapturic acids. Unlike copper-mediated N-arylation, the S-arylation of neither cysteine nor cystine derivatives proceeded satisfactorily in the presence of air.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
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