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

Matthew D. Wodrich | Zendy; Paola Caramenti | Zendy; Jérôme Waser | Zendy

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

Author(s) -

Matthew D. Wodrich,

Paola Caramenti,

Jérôme Waser

Publication year - 2015

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.5b03241

Subject(s) - chemistry , reagent , alkynylation , combinatorial chemistry , substituent , alkyne , sulfur , iodine , organic chemistry , catalysis

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.

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