Carbenoid and Vinylogous Reactivity of Diazo Arylidene Succinimide (DAS) with Benzyl Aryl Thioethers under Rhodium Catalysis

Abstract

Herein, we have explored the reactivity of diazo arylidene succinimide (DAS) with benzyl thioether to achieve [1,2]/[1,4]-Stevens rearrangement via rhodium catalysis. The protocol has successfully demonstrated the substituent-dependent competitive reactivity of DAS to tune the ratio of [1,2]-Stevens and [1,4]-Stevens rearrangement products. The protocol facilitated the formation of C–C and C–S bonds between carbenoid/vinylogous center. This catalytic protocol works smoothly in environmentally benign solvents to afford the corresponding desired products in moderate to good yields. The protocol proved to be scalable on gram quantity.