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Straightforward Synthesis of Indenes by Gold-Catalyzed Intramolecular Hydroalkylation of Ynamides

[Image: see text] An original and straightforward entry to polysubstituted indenes from readily available ynamides is reported. Upon reaction with a N-heterocyclic carbene–gold complex under mild conditions, activated keteniminium ions are generated whose unique electrophilicity triggers a [1,5]-hyd...

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Autores principales: Thilmany, Pierre, Guarnieri-Ibáñez, Alejandro, Jacob, Clément, Lacour, Jérôme, Evano, Gwilherm
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9954284/
https://www.ncbi.nlm.nih.gov/pubmed/36855401
http://dx.doi.org/10.1021/acsorginorgau.1c00021
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author Thilmany, Pierre
Guarnieri-Ibáñez, Alejandro
Jacob, Clément
Lacour, Jérôme
Evano, Gwilherm
author_facet Thilmany, Pierre
Guarnieri-Ibáñez, Alejandro
Jacob, Clément
Lacour, Jérôme
Evano, Gwilherm
author_sort Thilmany, Pierre
collection PubMed
description [Image: see text] An original and straightforward entry to polysubstituted indenes from readily available ynamides is reported. Upon reaction with a N-heterocyclic carbene–gold complex under mild conditions, activated keteniminium ions are generated whose unique electrophilicity triggers a [1,5]-hydride shift and a subsequent cyclization. The presence of an endocyclic enamide in the densely functionalized resulting indenes was shown to be especially useful and versatile, offering a range of opportunities for their further postfunctionalization.
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spelling pubmed-99542842023-02-27 Straightforward Synthesis of Indenes by Gold-Catalyzed Intramolecular Hydroalkylation of Ynamides Thilmany, Pierre Guarnieri-Ibáñez, Alejandro Jacob, Clément Lacour, Jérôme Evano, Gwilherm ACS Org Inorg Au [Image: see text] An original and straightforward entry to polysubstituted indenes from readily available ynamides is reported. Upon reaction with a N-heterocyclic carbene–gold complex under mild conditions, activated keteniminium ions are generated whose unique electrophilicity triggers a [1,5]-hydride shift and a subsequent cyclization. The presence of an endocyclic enamide in the densely functionalized resulting indenes was shown to be especially useful and versatile, offering a range of opportunities for their further postfunctionalization. American Chemical Society 2021-10-14 /pmc/articles/PMC9954284/ /pubmed/36855401 http://dx.doi.org/10.1021/acsorginorgau.1c00021 Text en © 2021 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 Thilmany, Pierre
Guarnieri-Ibáñez, Alejandro
Jacob, Clément
Lacour, Jérôme
Evano, Gwilherm
Straightforward Synthesis of Indenes by Gold-Catalyzed Intramolecular Hydroalkylation of Ynamides
title Straightforward Synthesis of Indenes by Gold-Catalyzed Intramolecular Hydroalkylation of Ynamides
title_full Straightforward Synthesis of Indenes by Gold-Catalyzed Intramolecular Hydroalkylation of Ynamides
title_fullStr Straightforward Synthesis of Indenes by Gold-Catalyzed Intramolecular Hydroalkylation of Ynamides
title_full_unstemmed Straightforward Synthesis of Indenes by Gold-Catalyzed Intramolecular Hydroalkylation of Ynamides
title_short Straightforward Synthesis of Indenes by Gold-Catalyzed Intramolecular Hydroalkylation of Ynamides
title_sort straightforward synthesis of indenes by gold-catalyzed intramolecular hydroalkylation of ynamides
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9954284/
https://www.ncbi.nlm.nih.gov/pubmed/36855401
http://dx.doi.org/10.1021/acsorginorgau.1c00021
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