Sulfonyl Chlorides as Thiol Surrogates for Carbon-Sulfur Bond Formation: One-Pot Synthesis of Thioethers and Thioesters

Torsten Cellnik, Alan R. Healy

Research output: Contribution to journalArticlepeer-review

Abstract

A method to synthesize thioethers and thioesters directly from readily available sulfonyl chlorides is reported. We demonstrate that a transient intermediate formed during phosphine-mediated deoxygenation of sulfonyl chlorides can be trapped in situ by activated alcohols or carboxylic acids to effect carbon-sulfur bond formation. The method is operationally simple and tolerates a broad range of functional groups. Special attention has been focused on the late-stage diversification of densely functionalized natural products and pharmaceuticals.

Original languageEnglish (US)
Pages (from-to)6454-6458
Number of pages5
JournalJournal of Organic Chemistry
Volume87
Issue number9
DOIs
StatePublished - May 6 2022

ASJC Scopus subject areas

  • Organic Chemistry

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