Sulfonyl Chlorides as Thiol Surrogates for Carbon–Sulfur Bond Formation: One-Pot Synthesis of Thioethers and Thioesters
Torsten Cellnik, Alan R. Healy
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.
Topics & Concepts
SulfonylChemistrySulfurDeoxygenationThiolOrganic chemistryPhosphineFunctional groupCombinatorial chemistryAlkylCatalysisPolymerSulfur-Based Synthesis TechniquesChemical Synthesis and ReactionsSynthesis and Catalytic Reactions