Formation of carbon-sulfur and carbon-selenium bonds by palladium-catalyzed decarboxylative cross-couplings of hindered 2,6-dialkoxybenzoic acids

J Org Chem. 2011 Aug 5;76(15):6327-30. doi: 10.1021/jo200344w. Epub 2011 Jul 6.

Abstract

A simple route to diaryl sulfides using a decarboxylative palladium-catalyzed reaction between electron-rich 2,6-dialkoxybenzoic acid derivatives and diaryl disulfides is reported. This coupling proceeds efficiently in the presence of Pd(CF(3)CO(2))(2) and Ag(2)CO(3) in a 65:1 mixture of 1,4-dioxane and tetramethylene sulfoxide (TMSO). We present also the first formation of a carbon-selenium bond via a palladium-catalyzed decarboxylative cross-coupling.