https://pubs.acs.org/doi/10.1021/acscatal.0c00394
Catalytic Deconstruction of N-Heteroaromatics to Functionalized Arylamines by Merging Hydrogen Transfer and Selective Coupling
Zhenda Tan,a Chenggang Ci,b Jian Yang,a Yang Wu,a Liang Cao,a Huanfeng Jianga and Min Zhanga,*
ABSTRACT: To date, although tremendous advances have been made on N-heteroaryl C−H functionalization, there remain significant unmet challenges in 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 a-sites of the initially formed N-heteroarenium salts followed by a C−N cleavage, proceeding with the striking features of broad substrate scope, excellent functional groups tolerance, high chemo-selectivity and atom-efficiency, and applicable for streamline synthesis of some biomedical molecules. The strategy utilized will pave the avenues for further development of catalytic transformations of inert organo-systems to functional frameworks.