Sulfonium salt formation-triggered regio- and Z-stereoselective phenoxythiolation of alkynes

Abstract

Sulfonium salt formation-triggered regio- and Z-stereoselective phenoxythiolation of alkynes with phenols and sulfoxides which allows the synthesis of sulfur-containing aryl alkenylethers under mild one-pot reaction conditions is reported. This reaction proceeds under mild conditions, is highly practical and easy to manipulate, and demonstrates a wide substrate scope with good functional group tolerance, furnishing excellent regio- and Z-stereoselective products in moderate to high yields. The synthetic utility of this approach is documented through gram-scale preparation, product derivatization and late-stage modification of complex bioactive molecules.