Gold(I)-Catalyzed Intermolecular Aryloxyvinylation with Acetylene Gas

[Image: see text] Acetylene gas is an important feedstock for chemical production, although it is underutilized in organic synthesis. We have developed an intermolecular gold(I)-catalyzed alkyne/alkene reaction of o-allylphenols with acetylene gas that gives rise to chromanes by a stereospecific ary...

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Autores principales: Medina-Gil, Tania, Sadurní, Anna, Hammarback, L. Anders, Echavarren, Antonio M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10442918/
https://www.ncbi.nlm.nih.gov/pubmed/37614519
http://dx.doi.org/10.1021/acscatal.3c02461
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author Medina-Gil, Tania
Sadurní, Anna
Hammarback, L. Anders
Echavarren, Antonio M.
author_facet Medina-Gil, Tania
Sadurní, Anna
Hammarback, L. Anders
Echavarren, Antonio M.
author_sort Medina-Gil, Tania
collection PubMed
description [Image: see text] Acetylene gas is an important feedstock for chemical production, although it is underutilized in organic synthesis. We have developed an intermolecular gold(I)-catalyzed alkyne/alkene reaction of o-allylphenols with acetylene gas that gives rise to chromanes by a stereospecific aryloxycyclization through the nucleophilic regioselective opening of cyclopropyl gold(I)-carbene intermediates. The synthetic application of this method was demonstrated in the late-stage functionalization of the natural product lapachol.
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spelling pubmed-104429182023-08-23 Gold(I)-Catalyzed Intermolecular Aryloxyvinylation with Acetylene Gas Medina-Gil, Tania Sadurní, Anna Hammarback, L. Anders Echavarren, Antonio M. ACS Catal [Image: see text] Acetylene gas is an important feedstock for chemical production, although it is underutilized in organic synthesis. We have developed an intermolecular gold(I)-catalyzed alkyne/alkene reaction of o-allylphenols with acetylene gas that gives rise to chromanes by a stereospecific aryloxycyclization through the nucleophilic regioselective opening of cyclopropyl gold(I)-carbene intermediates. The synthetic application of this method was demonstrated in the late-stage functionalization of the natural product lapachol. American Chemical Society 2023-08-01 /pmc/articles/PMC10442918/ /pubmed/37614519 http://dx.doi.org/10.1021/acscatal.3c02461 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Medina-Gil, Tania
Sadurní, Anna
Hammarback, L. Anders
Echavarren, Antonio M.
Gold(I)-Catalyzed Intermolecular Aryloxyvinylation with Acetylene Gas
title Gold(I)-Catalyzed Intermolecular Aryloxyvinylation with Acetylene Gas
title_full Gold(I)-Catalyzed Intermolecular Aryloxyvinylation with Acetylene Gas
title_fullStr Gold(I)-Catalyzed Intermolecular Aryloxyvinylation with Acetylene Gas
title_full_unstemmed Gold(I)-Catalyzed Intermolecular Aryloxyvinylation with Acetylene Gas
title_short Gold(I)-Catalyzed Intermolecular Aryloxyvinylation with Acetylene Gas
title_sort gold(i)-catalyzed intermolecular aryloxyvinylation with acetylene gas
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10442918/
https://www.ncbi.nlm.nih.gov/pubmed/37614519
http://dx.doi.org/10.1021/acscatal.3c02461
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AT hammarbacklanders goldicatalyzedintermoleculararyloxyvinylationwithacetylenegas
AT echavarrenantoniom goldicatalyzedintermoleculararyloxyvinylationwithacetylenegas

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