Publication

Alkynylation of Thiols with Ethynylbenziodoxolone (EBX) Reagents: alpha- or beta- pi-Addition?

Jérôme Waser, Matthew Wodrich, Paola Caramenti
2016
Journal Articles

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 beta-addition, alpha-elimination, and a 1,2-shift. Depending on the substituent on the alkyne, this mechanism can be favored over the previously disclosed concerted alpha-addition rti pathway.

Official source

https://infoscience.epfl.ch/entities/publication/e333adc4-96fd-44d4-b42f-f2133df95074

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Alkynylation of Thiols with Ethynylbenziodoxolone (EBX) Reagents: alpha- or beta- pi-Addition?

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