title: Alkynylation of Thiols with Ethynylbenziodoxolone (EBX) Reagents: α- or β- π-Addition?
abstract: 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.
authors.forename: Matthew D
authors.initials: MD
authors.lastname: Wodrich
authors.forename: Paola
authors.initials: P
authors.lastname: Caramenti
authors.affiliation: Laboratory of Catalysis and Organic Synthesis, Ecole Polytechnique Fédérale de Lausanne , EPFL SB ISIC LCSO, BCH 4306, 1015 Lausanne, Switzerland.
authors.forename: Jerome
authors.initials: J
authors.lastname: Waser