Three-Component Coupling Reactions of Aryne, DMSO, and Activated Alkyne: Stereoselective Synthesis of 2-[(o-Methylthio)aryloxy]-Substituted Dialkyl Maleates

A transition-metal-free coupling reaction of aryne, DMSO, and activated alkyne for the synthesis of 2-[(o-methylthio)aryloxy]-substituted dialkyl maleates is reported. This cascade process is associated with several bond cleavage as well as bond formation reactions in one pot. One of our synthesized maleates has been unambiguously established by single-crystal XRD studies. This methodology allows preparation of trisubstituted vinyl ethers with excellent stereospecificity.