The Discovery and Development of a Palladium(II)-Catalyzed Oxidative Cross-Coupling of Two Unactivated Arenes

Abstract

A review. The process of discovery and development of a palladium(II)-catalyzed oxidative cross-coupling of N-acetyl and N-pivaloylindoles with simple arom. compds. is described. Within this process inspiration was primarily derived from the organometallic literature and in particular the recent emergence of new and novel mechanisms for C-H bond cleavage by Pd(II)-complexes. During these studies it was realized that high levels of regio-control for C-H bond cleavage at indole could be obtained and subsequent investigation has led to the proposal of C3,C2-palladium migration for C2-arylation of N-pivaloylindole. The current state of the art in transition-metal catalyzed oxidative cross-coupling is also presented. [on SciFinder(R)]