Construction of multi-functionalized carbon chains by Ni-catalyzed carbosulfonylation of butadiene†

Abstract

Multi-functionalized carbon chains are prevalent motifs existing in various natural products and drugs. How to construct multi-functionalized carbon chains represents a meaningful task. Herein, we developed a photo-induced stereoselective 1,4-carbosulfonylation of butadiene to construct multi-functionalized carbon chains under nickel catalysis. A wide variety of aryl iodides and sodium sulfinates could be facilely coupled with butadiene to generate difunctionalized olefin intermediates. Taking advantage of the internal CC bond, various functional groups have been efficiently incorporated to construct multi-functionalized aliphatic compounds. A scale-up reaction, an iterative reaction and late-stage modifications have been performed to further demonstrate the synthetic utility of this protocol.