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

[Image: see text] 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...

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Autores principales: Wodrich, Matthew D., Caramenti, Paola, Waser, Jerome
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2015
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4700532/
https://www.ncbi.nlm.nih.gov/pubmed/26652212
http://dx.doi.org/10.1021/acs.orglett.5b03241
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author Wodrich, Matthew D.
Caramenti, Paola
Waser, Jerome
author_facet Wodrich, Matthew D.
Caramenti, Paola
Waser, Jerome
author_sort Wodrich, Matthew D.
collection PubMed
description [Image: see text] 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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spelling pubmed-47005322016-01-19 Alkynylation of Thiols with Ethynylbenziodoxolone (EBX) Reagents: α- or β- π-Addition? Wodrich, Matthew D. Caramenti, Paola Waser, Jerome Org Lett [Image: see text] 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. American Chemical Society 2015-12-14 2016-01-04 /pmc/articles/PMC4700532/ /pubmed/26652212 http://dx.doi.org/10.1021/acs.orglett.5b03241 Text en Copyright © 2015 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Wodrich, Matthew D.
Caramenti, Paola
Waser, Jerome
Alkynylation of Thiols with Ethynylbenziodoxolone (EBX) Reagents: α- or β- π-Addition?
title Alkynylation of Thiols with Ethynylbenziodoxolone (EBX) Reagents: α- or β- π-Addition?
title_full Alkynylation of Thiols with Ethynylbenziodoxolone (EBX) Reagents: α- or β- π-Addition?
title_fullStr Alkynylation of Thiols with Ethynylbenziodoxolone (EBX) Reagents: α- or β- π-Addition?
title_full_unstemmed Alkynylation of Thiols with Ethynylbenziodoxolone (EBX) Reagents: α- or β- π-Addition?
title_short Alkynylation of Thiols with Ethynylbenziodoxolone (EBX) Reagents: α- or β- π-Addition?
title_sort alkynylation of thiols with ethynylbenziodoxolone (ebx) reagents: α- or β- π-addition?
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4700532/
https://www.ncbi.nlm.nih.gov/pubmed/26652212
http://dx.doi.org/10.1021/acs.orglett.5b03241
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