Rhodium(III)-Catalyzed Dearomatizing (3 + 2) Annulation of 2-Alkenylphenols and Alkynes

[Image: see text] Appropriately substituted 2-alkenylphenols undergo a mild formal [3C+2C] cycloaddition with alkynes when treated with a Rh(III) catalyst and an oxidant. The reaction, which involves the cleavage of the terminal C–H bond of the alkenyl moiety and the dearomatization of the phenol ri...

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Autores principales: Seoane, Andrés, Casanova, Noelia, Quiñones, Noelia, Mascareñas, José L., Gulías, Moisés
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4077242/
https://www.ncbi.nlm.nih.gov/pubmed/24820195
http://dx.doi.org/10.1021/ja5034952
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author Seoane, Andrés
Casanova, Noelia
Quiñones, Noelia
Mascareñas, José L.
Gulías, Moisés
author_facet Seoane, Andrés
Casanova, Noelia
Quiñones, Noelia
Mascareñas, José L.
Gulías, Moisés
author_sort Seoane, Andrés
collection PubMed
description [Image: see text] Appropriately substituted 2-alkenylphenols undergo a mild formal [3C+2C] cycloaddition with alkynes when treated with a Rh(III) catalyst and an oxidant. The reaction, which involves the cleavage of the terminal C–H bond of the alkenyl moiety and the dearomatization of the phenol ring, provides a versatile and efficient approach to highly appealing spirocyclic skeletons and occurs with high selectivity.
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spelling pubmed-40772422014-07-01 Rhodium(III)-Catalyzed Dearomatizing (3 + 2) Annulation of 2-Alkenylphenols and Alkynes Seoane, Andrés Casanova, Noelia Quiñones, Noelia Mascareñas, José L. Gulías, Moisés J Am Chem Soc [Image: see text] Appropriately substituted 2-alkenylphenols undergo a mild formal [3C+2C] cycloaddition with alkynes when treated with a Rh(III) catalyst and an oxidant. The reaction, which involves the cleavage of the terminal C–H bond of the alkenyl moiety and the dearomatization of the phenol ring, provides a versatile and efficient approach to highly appealing spirocyclic skeletons and occurs with high selectivity. American Chemical Society 2014-05-12 2014-05-28 /pmc/articles/PMC4077242/ /pubmed/24820195 http://dx.doi.org/10.1021/ja5034952 Text en Copyright © 2014 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Seoane, Andrés
Casanova, Noelia
Quiñones, Noelia
Mascareñas, José L.
Gulías, Moisés
Rhodium(III)-Catalyzed Dearomatizing (3 + 2) Annulation of 2-Alkenylphenols and Alkynes
title Rhodium(III)-Catalyzed Dearomatizing (3 + 2) Annulation of 2-Alkenylphenols and Alkynes
title_full Rhodium(III)-Catalyzed Dearomatizing (3 + 2) Annulation of 2-Alkenylphenols and Alkynes
title_fullStr Rhodium(III)-Catalyzed Dearomatizing (3 + 2) Annulation of 2-Alkenylphenols and Alkynes
title_full_unstemmed Rhodium(III)-Catalyzed Dearomatizing (3 + 2) Annulation of 2-Alkenylphenols and Alkynes
title_short Rhodium(III)-Catalyzed Dearomatizing (3 + 2) Annulation of 2-Alkenylphenols and Alkynes
title_sort rhodium(iii)-catalyzed dearomatizing (3 + 2) annulation of 2-alkenylphenols and alkynes
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4077242/
https://www.ncbi.nlm.nih.gov/pubmed/24820195
http://dx.doi.org/10.1021/ja5034952
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