Ruthenium-Catalyzed Chemo-Selective Carbene Insertion into C–H Bond of Styrene over Cyclopropanation: C–C Bond Formation

Abstract

The C–C bond formation reactions are important in organic synthesis. Heck reaction is known to arylate the terminal carbon of olefins; however, direct alkylation of the terminal carbon of olefin is limited. Herein, we report a novel ruthenium-catalyzed selective cross-coupling reaction of styrene and α-diazoesters to form a new C–C bond over cyclopropanation via the C–H insertion process for the first time. Using this novel methodology, a wide variety of substrates have been utilized and a variety of α-vinylated benzylic esters and densely functionalized olefins have been synthesized with good stereoselectivity under mild reaction conditions. The overall reaction process proceeds through the carbene insertion into styrene to form the desired products in good to excellent yields with proper stereoselectivity. The selective C–H inserted product, wide substrate scope, and excellent functional group tolerance are the best features of this work.