Platinum-Catalyzed C–H Arylation of Simple Arenes

by Anna M. Wagner, Amanda J. Hickman and Melanie S. Sanford*

This report describes the Na2PtCl4 catalyzed C–H arylation of arene substrates with diaryliodonium salts. The site selectivity of these reactions is predominantly controlled by steric factors. Remarkably, Na2PtCl4-catalyzed naphthalene arylation proceeds with opposite site selectivity compared to that obtained with Na2PdCl4 as the catalyst. Preliminary mechanistic studies provide evidence for a PtII/PtIV catalytic cycle involving rate-limiting C–C bond-forming reductive elimination.

Journal of the American Chemical Society

DOI: 10.1021/ja408112j