Iodo-sulphonylation of 1,6-enynones: a metal-free strategy to synthesize N-substituted succinimides

Abstract

An iodine-mediated radical cyclization of 1,6-enynones with sulphonyl hydrazides using tert-butyl hydroperoxide (TBHP) as the oxidant has been developed for the synthesis of iodo-sulphonylated-succinimide derivatives. The notable advantages of the developed method are metal-free conditions, broad functional group tolerance, column chromatography-free purification, high stereoselectivity (E isomer), shorter reaction times, and the cascade construction of three new bonds (C–S, C–I, and C–C). The synthetic application of the iodo-functionality has been extended to the Heck coupling reaction with acrylonitrile and to the Suzuki coupling reaction with benzene boronic acid.