Graphene-Catalyzed Direct Friedel–Crafts Alkylation Reactions: Mechanism, Selectivity, and Synthetic Utility

• DOI: 10.1021/jacs.5b09636
• Publication Date: 2015-10-23T13:01:40Z
• Authors: Feng Hu; Mehulkumar Patel; Feixiang Luo; Carol Flach; Richard Mendelsohn; Eric Garfunkel; Huixin He; Michal Szostak
• Keywords: Functional group; Tandem

Transition-metal-catalyzed alkylation reactions of arenes have become a central transformation in organic synthesis. Herein, we report the first general strategy for with styrenes and alcohols catalyzed by carbon-based materials, exploiting unique property graphenes to produce valuable diarylalkane products high yields excellent regioselectivity. The protocol is characterized wide substrate scope functional group tolerance. Notably, this process constitutes application promote direct C–C bond formation utilizing polar groups anchored on GO surface, thus opening door an array alkylations using benign readily available graphene materials. Mechanistic studies suggest that reaction proceeds via tandem catalysis mechanism which both coupling partners are activated interaction surface.