Dual roles of sulfonyl hydrazides in the catalyst-free sulfonylation of unsaturated benzylic alcohols in water

Abstract

An atom-economical sulfonylation of unsaturated benzylic alcohols in water is described. In this transformation, dual roles of sulfonyl hydrazides serving as both a sulfonyl source and a reductant have been demonstrated, which enabled a facile and green method to synthesize alkyl sulfones from unsaturated benzylic alcohols. Moreover, this approach provides a practical access to deuterated alkanes from the corresponding alkenes by employing the combination of sulfonyl hydrazides and the solvent D₂O.