Palladium-catalyzed aminative cross-coupling of aryl thianthrenium salts with arylboronic acid and DPPH

Abstract

An efficient palladium-catalyzed aminative cross-coupling of arylboronic acids and O-(diphenylphosphinyl)hydroxylamine (DPPH) with readily accessible and robust aryl thianthrenium salts was developed. The three-component couplings proceeded effectively via C-S bond cleavage under palladium catalysis in the presence of tBuONa in acetonitrile to produce a variety of diarylamines in modest-to-high yields. The reactions employing aryl thianthrenium salts as effective arylating agents displayed both good substrate scope and wide functional group compatibility. In addition, the protocol could be easily subjected to scale-up preparation and the late-stage modification of complex molecule. Mechanistic studies revealed that in situ generated aniline via the coupling of arylboronic acid with DPPH possibly functions as the pivotal intermediate of the reaction.