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Au–Ag Bimetallic Catalysis: 3‐Alkynyl Benzofurans from Phenols via Tandem C−H Alkynylation/Oxy‐Alkynylation

The development of new methodologies enabling a facile access to valuable heterocyclic frameworks still is an important subject of research. In this context, we describe a dual catalytic cycle merging C−H alkynylation of phenols and oxy‐alkynylation of the newly introduced triple bond by using a uni...

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Autores principales: Hu, Long, Dietl, Martin C., Han, Chunyu, Rudolph, Matthias, Rominger, Frank, Hashmi, A. Stephen K.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8252013/
https://www.ncbi.nlm.nih.gov/pubmed/33617065
http://dx.doi.org/10.1002/anie.202016595
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author Hu, Long
Dietl, Martin C.
Han, Chunyu
Rudolph, Matthias
Rominger, Frank
Hashmi, A. Stephen K.
author_facet Hu, Long
Dietl, Martin C.
Han, Chunyu
Rudolph, Matthias
Rominger, Frank
Hashmi, A. Stephen K.
author_sort Hu, Long
collection PubMed
description The development of new methodologies enabling a facile access to valuable heterocyclic frameworks still is an important subject of research. In this context, we describe a dual catalytic cycle merging C−H alkynylation of phenols and oxy‐alkynylation of the newly introduced triple bond by using a unique redox property and the carbophilic π acidity of gold. Mechanistic studies support the participation of a bimetallic gold–silver species. The one‐pot protocol offers a direct, simple, and regio‐specific approach to 3‐alkynyl benzofurans from readily available phenols. A broad range of substrates, including heterocycles, is transferred with excellent functional group tolerance. Thus, this methodology can be used for the late‐stage incorporation of benzofurans.
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spelling pubmed-82520132021-07-07 Au–Ag Bimetallic Catalysis: 3‐Alkynyl Benzofurans from Phenols via Tandem C−H Alkynylation/Oxy‐Alkynylation Hu, Long Dietl, Martin C. Han, Chunyu Rudolph, Matthias Rominger, Frank Hashmi, A. Stephen K. Angew Chem Int Ed Engl Communications The development of new methodologies enabling a facile access to valuable heterocyclic frameworks still is an important subject of research. In this context, we describe a dual catalytic cycle merging C−H alkynylation of phenols and oxy‐alkynylation of the newly introduced triple bond by using a unique redox property and the carbophilic π acidity of gold. Mechanistic studies support the participation of a bimetallic gold–silver species. The one‐pot protocol offers a direct, simple, and regio‐specific approach to 3‐alkynyl benzofurans from readily available phenols. A broad range of substrates, including heterocycles, is transferred with excellent functional group tolerance. Thus, this methodology can be used for the late‐stage incorporation of benzofurans. John Wiley and Sons Inc. 2021-03-30 2021-05-03 /pmc/articles/PMC8252013/ /pubmed/33617065 http://dx.doi.org/10.1002/anie.202016595 Text en © 2021 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH https://creativecommons.org/licenses/by-nc-nd/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc-nd/4.0/ (https://creativecommons.org/licenses/by-nc-nd/4.0/) License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made.
spellingShingle Communications
Hu, Long
Dietl, Martin C.
Han, Chunyu
Rudolph, Matthias
Rominger, Frank
Hashmi, A. Stephen K.
Au–Ag Bimetallic Catalysis: 3‐Alkynyl Benzofurans from Phenols via Tandem C−H Alkynylation/Oxy‐Alkynylation
title Au–Ag Bimetallic Catalysis: 3‐Alkynyl Benzofurans from Phenols via Tandem C−H Alkynylation/Oxy‐Alkynylation
title_full Au–Ag Bimetallic Catalysis: 3‐Alkynyl Benzofurans from Phenols via Tandem C−H Alkynylation/Oxy‐Alkynylation
title_fullStr Au–Ag Bimetallic Catalysis: 3‐Alkynyl Benzofurans from Phenols via Tandem C−H Alkynylation/Oxy‐Alkynylation
title_full_unstemmed Au–Ag Bimetallic Catalysis: 3‐Alkynyl Benzofurans from Phenols via Tandem C−H Alkynylation/Oxy‐Alkynylation
title_short Au–Ag Bimetallic Catalysis: 3‐Alkynyl Benzofurans from Phenols via Tandem C−H Alkynylation/Oxy‐Alkynylation
title_sort au–ag bimetallic catalysis: 3‐alkynyl benzofurans from phenols via tandem c−h alkynylation/oxy‐alkynylation
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8252013/
https://www.ncbi.nlm.nih.gov/pubmed/33617065
http://dx.doi.org/10.1002/anie.202016595
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