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

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

  • Wodrich MD Laboratory of Catalysis and Organic Synthesis, Ecole Polytechnique Fédérale de Lausanne , EPFL SB ISIC LCSO, BCH 4306, 1015 Lausanne, Switzerland.
  • Caramenti P
  • Waser J
  • 2015-12-15
Published in:
  • Organic letters. - 2016
Physical and Theoretical Chemistry
Organic Chemistry
Biochemistry
English 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.
Language
  • English
Open access status
hybrid
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Persistent URL
https://sonar.ch/global/documents/197680
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