Zinc–gold cooperative catalysis for the direct alkynylation of benzofurans

The direct alkynylation of benzofurans was achieved for the first time using the hypervalent iodine reagent 1-[(triisopropylsilyl)ethynyl]-1,2-benziodoxol-3(1H)-one (TIPS-EBX) based on the cooperative effect between a gold catalyst and a zinc Lewis acid. High selectivity was observed for C2-alkynyla...

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Detalles Bibliográficos
Autores principales: Li, Yifan, Waser, Jérôme
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2013
Materias:
Letter
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3778369/
https://www.ncbi.nlm.nih.gov/pubmed/24062840
http://dx.doi.org/10.3762/bjoc.9.204
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author Li, Yifan
Waser, Jérôme
author_facet Li, Yifan
Waser, Jérôme
author_sort Li, Yifan
collection PubMed
description The direct alkynylation of benzofurans was achieved for the first time using the hypervalent iodine reagent 1-[(triisopropylsilyl)ethynyl]-1,2-benziodoxol-3(1H)-one (TIPS-EBX) based on the cooperative effect between a gold catalyst and a zinc Lewis acid. High selectivity was observed for C2-alkynylation of benzofurans substituted with alkyl, aryl, halogen and ether groups. The reaction was also successful in the case of the more complex drug 8-methoxypsoralen (8-MOP).
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spelling pubmed-37783692013-09-23 Zinc–gold cooperative catalysis for the direct alkynylation of benzofurans Li, Yifan Waser, Jérôme Beilstein J Org Chem Letter The direct alkynylation of benzofurans was achieved for the first time using the hypervalent iodine reagent 1-[(triisopropylsilyl)ethynyl]-1,2-benziodoxol-3(1H)-one (TIPS-EBX) based on the cooperative effect between a gold catalyst and a zinc Lewis acid. High selectivity was observed for C2-alkynylation of benzofurans substituted with alkyl, aryl, halogen and ether groups. The reaction was also successful in the case of the more complex drug 8-methoxypsoralen (8-MOP). Beilstein-Institut 2013-08-29 /pmc/articles/PMC3778369/ /pubmed/24062840 http://dx.doi.org/10.3762/bjoc.9.204 Text en Copyright © 2013, Li and Waser https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Letter
Li, Yifan
Waser, Jérôme
Zinc–gold cooperative catalysis for the direct alkynylation of benzofurans
title Zinc–gold cooperative catalysis for the direct alkynylation of benzofurans
title_full Zinc–gold cooperative catalysis for the direct alkynylation of benzofurans
title_fullStr Zinc–gold cooperative catalysis for the direct alkynylation of benzofurans
title_full_unstemmed Zinc–gold cooperative catalysis for the direct alkynylation of benzofurans
title_short Zinc–gold cooperative catalysis for the direct alkynylation of benzofurans
title_sort zinc–gold cooperative catalysis for the direct alkynylation of benzofurans
topic Letter
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3778369/
https://www.ncbi.nlm.nih.gov/pubmed/24062840
http://dx.doi.org/10.3762/bjoc.9.204
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AT waserjerome zincgoldcooperativecatalysisforthedirectalkynylationofbenzofurans

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