Addition of arylstannanes to alkynes giving ortho-alkenylarylstannanes catalysed cooperatively by a rhodium complex and zinc chloride

The reaction of arylstannanes ArSnR(3) with unfunctionalised alkynes was found to proceed in the presence of a rhodium catalyst and a catalytic amount of zinc chloride to give ortho-alkenylarylstannanes with high selectivity in high yields. The catalytic cycle is very unique, consisting of three tra...

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Autores principales: Ming, Jialin, Shi, Qi, Hayashi, Tamio
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2018
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6182567/
https://www.ncbi.nlm.nih.gov/pubmed/30393531
http://dx.doi.org/10.1039/c8sc02459f
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author Ming, Jialin
Shi, Qi
Hayashi, Tamio
author_facet Ming, Jialin
Shi, Qi
Hayashi, Tamio
author_sort Ming, Jialin
collection PubMed
description The reaction of arylstannanes ArSnR(3) with unfunctionalised alkynes was found to proceed in the presence of a rhodium catalyst and a catalytic amount of zinc chloride to give ortho-alkenylarylstannanes with high selectivity in high yields. The catalytic cycle is very unique, consisting of three transmetalation steps, from Sn to Rh, Rh to Zn, and Zn to Sn, in addition to arylrhodation of alkyne followed by 1,4-migration of Rh from 2-arylalkenyl carbon to ortho-alkenylaryl carbon.
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spelling pubmed-61825672018-11-02 Addition of arylstannanes to alkynes giving ortho-alkenylarylstannanes catalysed cooperatively by a rhodium complex and zinc chloride Ming, Jialin Shi, Qi Hayashi, Tamio Chem Sci Chemistry The reaction of arylstannanes ArSnR(3) with unfunctionalised alkynes was found to proceed in the presence of a rhodium catalyst and a catalytic amount of zinc chloride to give ortho-alkenylarylstannanes with high selectivity in high yields. The catalytic cycle is very unique, consisting of three transmetalation steps, from Sn to Rh, Rh to Zn, and Zn to Sn, in addition to arylrhodation of alkyne followed by 1,4-migration of Rh from 2-arylalkenyl carbon to ortho-alkenylaryl carbon. Royal Society of Chemistry 2018-08-17 /pmc/articles/PMC6182567/ /pubmed/30393531 http://dx.doi.org/10.1039/c8sc02459f Text en This journal is © The Royal Society of Chemistry 2018 http://creativecommons.org/licenses/by/3.0/ This article is freely available. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence (CC BY 3.0)
spellingShingle Chemistry
Ming, Jialin
Shi, Qi
Hayashi, Tamio
Addition of arylstannanes to alkynes giving ortho-alkenylarylstannanes catalysed cooperatively by a rhodium complex and zinc chloride
title Addition of arylstannanes to alkynes giving ortho-alkenylarylstannanes catalysed cooperatively by a rhodium complex and zinc chloride
title_full Addition of arylstannanes to alkynes giving ortho-alkenylarylstannanes catalysed cooperatively by a rhodium complex and zinc chloride
title_fullStr Addition of arylstannanes to alkynes giving ortho-alkenylarylstannanes catalysed cooperatively by a rhodium complex and zinc chloride
title_full_unstemmed Addition of arylstannanes to alkynes giving ortho-alkenylarylstannanes catalysed cooperatively by a rhodium complex and zinc chloride
title_short Addition of arylstannanes to alkynes giving ortho-alkenylarylstannanes catalysed cooperatively by a rhodium complex and zinc chloride
title_sort addition of arylstannanes to alkynes giving ortho-alkenylarylstannanes catalysed cooperatively by a rhodium complex and zinc chloride
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6182567/
https://www.ncbi.nlm.nih.gov/pubmed/30393531
http://dx.doi.org/10.1039/c8sc02459f
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AT shiqi additionofarylstannanestoalkynesgivingorthoalkenylarylstannanescatalysedcooperativelybyarhodiumcomplexandzincchloride
AT hayashitamio additionofarylstannanestoalkynesgivingorthoalkenylarylstannanescatalysedcooperativelybyarhodiumcomplexandzincchloride

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