Visible-light promoted aerobic difunctionalization of alkenes with sulfonyl hydrazides for the synthesis of β-keto/hydroxyl sulfones

Abstract

A practical method has been developed for the conversion of alkenes to β-keto/hydroxyl sulfones by their reaction with sulfonyl hydrazides under metal-free conditions.

Sulfonyl Hydrazides in Organic Synthesis: A Review of Recent Studies

“…Normally, copper‐oxidant systems were efficient. Besides, both photosynthesis and electrosynthesis were also well investigated in these years. The radical addition to unsaturated bonds, C−H activation and coupling were all effective, which will be fully discussed herein.…”

“…Wang, Liu and Zhu elaborated the oxygen‐mediated oxysulfonylations of styrenes, which involved a radical adduct and C−O coupling mechanism (Eq. 11‐1).…”

“…11‐1). They reported that the copper catalyst, Brønsted acid or visible‐light was effective for these transformations. The Tang group found that even using water in oxysulfonylations of N,N ‐dimethylenaminones gave same products (Eq.…”

Advances in Oxosulfonylation Reaction

“…In 2019, Zhu group [57] developed a metal-free oxosulfonylation methodology of alkenes 16a for synthesis of β-keto-sulfones 16c using sulfonylhydrazide 16b as sulfonyl source, methylene blue (MB) as organophotocatalyst and 1,4-diazabicyclo[2. keto-sulfones using various alkenes and sulfonylhydrazides. The authors proposed a plausible mechanism for this reaction based on control experiments and earlier reports (Scheme 16).…”

“…In light of its extensive efficacies, numerous protocols of oxosulfonylation such as metal-catalyzed oxosulfonylation, [46][47][48][49][50][51][52][53][54][55] organophotocatalyzed oxosulfonylation, [32,[56][57][58] metal-based photocatalyzed oxosulfonylation, [59][60][61] catalyst free photo-induced oxosulfonylation [62][63][64] etc have been developed. Very recently, oxygen triggered oxosulfonylation methods [65][66][67][68][69][70][71][72] show great interest among synthetic organic chemists.…”