Synthesis of aryl sulfides by decarboxylative C-S cross-couplings

Abstract

A study was conducted to demonstrate the transition-metal-catalyzed synthesis of aryl sulfides by decarboxylative C-S cross-couplings. Coupling reaction of 2-nitrobenzoic acid with 1-octanethiol were carried in the presence of different combinations of transition-metal catalysts at elevated temperatures to investigate the synthesis process and identify an effective catalyst system. The investigations showed that these reactions formed decarboxylative coupling products containing a mixture of nitrobenzene and aminobenzene sulfides. It was also demonstrated that reactions conducted with monometallic PdII, CuII, or bimetallic CuII, AgI, PdII, and AgI catalysts resulted in low conversions of starting materials. A wide range of aryl carboxylic acids were tested as substrates for C-S coupling to expand the scope of the method.