Rhodium(III)-Catalyzed Switchable β-C(sp2)-H Alkenylation and Alkylation of Acyclic Enamides with Allyl Alcohols.

Abstract

Herein, rhodium(III)-catalyzed β-C(sp2)-H alkenylation and alkylation of enamides are presented using readily accessible allylic alcohols by switching the reaction conditions. This tunable transformation has been applied to a wide range of substrates and typically proceeded with excellent regioselectivity and stereoselectivity as well as with good functional group tolerance. The catalytic system offers an efficient approach for synthesizing various functionalized enamides bearing N-(2Z,4E)-butadiene and (Z)-β-C(sp2)-H alkylated enamides. In addition, mechanistic experiments suggest that Rh(III)-catalyzed C-H activation is not related to the critical step.