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The alkynylation of thiols with EthynylBenziodoXolone (EBX) reagents is a fast and chemoselective method for the synthesis of thioalkynes. Combined experimental and computational studies are reported, which led to the identification of a new mechanism for this reaction, proceeding via an initial sulfur-iodine interaction followed by β-addition, α-elimination, and a 1,2-shift. Depending on the substituent on the alkyne, this mechanism can be favored over the previously disclosed concerted α-addition pathway.

Alkynylation of Thiols with Ethynylbenziodoxolone (EBX) Reagents: α- or β- π-Addition?