Catalytic Conversion of N-Heteroaromatics to Functionalized Arylamines by Merging Hydrogen Transfer and Selective Coupling
Zhenda Tan, Chenggang Ci, Jian Yang, Yang Wu, Liang Cao, Huanfeng Jiang, Min Zhang
Abstract
To date, although tremendous advances have been made in N-heteroaryl C–H functionalization, there remain significant unmet challenges in the deconstruction of extensively applied but poorly reactive N-heteroaromatics to useful frameworks. Here, by a strategy merging hydrogen transfer and selective coupling, we present a ruthenium-catalyzed deconstruction of N-heteroaromatics to functionalized arylamines with 2-aminoaryl methanols. The reaction is achieved via sequential functionalization of the β and α sites of the initially formed N-heteroarenium salts followed by a C–N cleavage, which proceeds with the striking features of broad substrate scope, excellent functional group tolerance, high chemoselectivity and atom efficiency, and suitability for a streamlined synthesis of some biomedical molecules. The strategy utilized will pave the way for further development of catalytic transformations of inert organo systems to functional frameworks.