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April 15, 2026Organic Letters2 citations

Formal Regioselective C–H Sulfinylation of Alkenes with Sulfinyl Sulfones

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XSXinyu SongHebei UniversityYXYilin XingHebei UniversityRGRuikang GaoHebei University

Key Points

  • The aim is to develop a new method to incorporate sulfinyl groups into alkenes efficiently.
  • Developed a novel sulfinylation reaction.
  • Used sulfinyl sulfones as sulfur-transfer reagents.
  • Conducted mechanistic investigations with control experiments.
  • Achieved excellent regioselectivity in the sulfinylation process.
  • Synthesis of alkenyl sulfoxides demonstrated under mild reaction conditions.
  • Radical addition-coupling followed by E2 elimination was identified as the reaction mechanism.

Abstract

Sulfinyl sulfones represent a versatile class of sulfur-transfer reagents. In this work, we developed a novel application for these reagents through the direct incorporation of sulfinyl moieties into alkenes, providing an efficient and facile protocol for the synthesis of alkenyl sulfoxides. This methodology is distinguished by its mild reaction conditions, operational simplicity, and excellent regioselectivity. Mechanistic investigations through control experiments reveal that the reaction proceeds via a radical addition-coupling followed by an E2 elimination sequence.

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Cite This Study

Song et al. (2026) studied this question.

synapsesocial.com/papers/69df2b04e4eeef8a2a6aff5chttps://doi.org/10.1021/acs.orglett.6c01034
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