Substituent-Promoted Thio-Belluš–Claisen Rearrangement with Difluoroketene

Organic Letters 2026

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Authors: Sheng Xi, Hongrui Zhang, Xi Zhang, Geng Huang, Yu Zhang, Chi Zhang, C Feng
DOI: 10.1021/acs.orglett.6c00293
Cited by: 1
References: 77

Abstract

The thio-Belluš-Claisen rearrangement with difluoroketene is reported herein. By resorting to fluoride-initiated desilylative β-elimination of difluorobromoacetylsilane, a new protocol that enables controlled release of the unstable difluoroketene and its efficient capture by allyl thioether for the ensuing rearrangement is successfully developed. The presence of an electron-withdrawing group on the internal alkene site of allyl thioether is proven to be vital for this reaction by promoting the rearrangement through charge stabilization in the transition state.

Fields of Study & Subjects

Fluorine in Organic Chemistry Synthesis and Characterization of Pyrroles Sulfur-Based Synthesis Techniques

Publication details

Journal / source
Organic Letters
Publisher
American Chemical Society (ACS)
Volume
28
Issue
10
Pages
3249–3254
Publication date
3 March 2026
Language
EN