A Sulfur Monoxide Surrogate Designed for the Synthesis of Sulfoxides and Sulfinamides**

Abstract

AbstractSulfur monoxide (SO) is a highly reactive species that cannot be isolated in bulk. However, SO can play a pivotal role as a fundamental building block in organic synthesis. Reported herein is the design and application of a sulfinylhydrazine reagent as an easily prepared sulfur monoxide surrogate. We show facile thermal SO transfer from this reagent to dienes where a reaction using a mechanistic probe suggests the generation of singlet SO. Combined with Grignard reagents and appropriate carbon or nitrogen electrophiles, the reagent serves as an effective “SO” donor to enable the one‐pot, three‐component synthesis of sulfoxides and sulfinamides.