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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...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2021
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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. |
format | Online Article Text |
id | pubmed-9954284 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
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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