N‐Iodosuccinimide as Bifunctional Reagent in (E)‐Selective C(sp2)−H Sulfonylation of Styrenes

Abstract

AbstractHerein we report the use of N‐iodosuccinimide (NIS) as a bifunctional reagent for a regio‐ and (E)‐selective C(sp2)‐H sulfonylation reaction of styrenes. Styrenes and sulfonyl hydrazides treated with NIS and potassium carbonate in ethanol at 70 °C resulted in (E)‐vinyl sulfones exclusively with good to excellent yields. NIS, plays a dual role to generate sulfonyl radical from sulfonyl hydrazides at an initial stage and finally gives β‐iodosulfone intermediate which was further converted to (E)‐vinyl sulfones. Overall, a sustainable method for mild, metal free, convenient, one pot and direct synthesis of (E)‐vinyl sulfones from styrenes are demonstrated via a C−S coupling reaction.