Palladium(II)-Catalyzed Annulation between ortho-Alkenylphenols and Allenes. Key Role of the Metal Geometry in Determining the Reaction Outcome

[Image: see text] 2-Alkenylphenols react with allenes, upon treatment with catalytic amounts of Pd(II) and Cu(II), to give benzoxepine products in high yields and with very good regio- and diastereoselectivities. This contrasts with the results obtained with Rh catalysts, which provided chromene-lik...

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Autores principales: Casanova, Noelia, Del Rio, Karina P., García-Fandiño, Rebeca, Mascareñas, José L., Gulías, Moisés
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2016
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5084065/
https://www.ncbi.nlm.nih.gov/pubmed/27807509
http://dx.doi.org/10.1021/acscatal.6b00739
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author Casanova, Noelia
Del Rio, Karina P.
García-Fandiño, Rebeca
Mascareñas, José L.
Gulías, Moisés
author_facet Casanova, Noelia
Del Rio, Karina P.
García-Fandiño, Rebeca
Mascareñas, José L.
Gulías, Moisés
author_sort Casanova, Noelia
collection PubMed
description [Image: see text] 2-Alkenylphenols react with allenes, upon treatment with catalytic amounts of Pd(II) and Cu(II), to give benzoxepine products in high yields and with very good regio- and diastereoselectivities. This contrasts with the results obtained with Rh catalysts, which provided chromene-like products through a pathway involving a β-hydrogen elimination step. Computational studies suggest that the square planar geometry of the palladium is critical to favor the reductive elimination process required for the formation of the oxepine products.
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spelling pubmed-50840652016-10-31 Palladium(II)-Catalyzed Annulation between ortho-Alkenylphenols and Allenes. Key Role of the Metal Geometry in Determining the Reaction Outcome Casanova, Noelia Del Rio, Karina P. García-Fandiño, Rebeca Mascareñas, José L. Gulías, Moisés ACS Catal [Image: see text] 2-Alkenylphenols react with allenes, upon treatment with catalytic amounts of Pd(II) and Cu(II), to give benzoxepine products in high yields and with very good regio- and diastereoselectivities. This contrasts with the results obtained with Rh catalysts, which provided chromene-like products through a pathway involving a β-hydrogen elimination step. Computational studies suggest that the square planar geometry of the palladium is critical to favor the reductive elimination process required for the formation of the oxepine products. American Chemical Society 2016-04-14 2016-05-06 /pmc/articles/PMC5084065/ /pubmed/27807509 http://dx.doi.org/10.1021/acscatal.6b00739 Text en Copyright © 2016 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 Casanova, Noelia
Del Rio, Karina P.
García-Fandiño, Rebeca
Mascareñas, José L.
Gulías, Moisés
Palladium(II)-Catalyzed Annulation between ortho-Alkenylphenols and Allenes. Key Role of the Metal Geometry in Determining the Reaction Outcome
title Palladium(II)-Catalyzed Annulation between ortho-Alkenylphenols and Allenes. Key Role of the Metal Geometry in Determining the Reaction Outcome
title_full Palladium(II)-Catalyzed Annulation between ortho-Alkenylphenols and Allenes. Key Role of the Metal Geometry in Determining the Reaction Outcome
title_fullStr Palladium(II)-Catalyzed Annulation between ortho-Alkenylphenols and Allenes. Key Role of the Metal Geometry in Determining the Reaction Outcome
title_full_unstemmed Palladium(II)-Catalyzed Annulation between ortho-Alkenylphenols and Allenes. Key Role of the Metal Geometry in Determining the Reaction Outcome
title_short Palladium(II)-Catalyzed Annulation between ortho-Alkenylphenols and Allenes. Key Role of the Metal Geometry in Determining the Reaction Outcome
title_sort palladium(ii)-catalyzed annulation between ortho-alkenylphenols and allenes. key role of the metal geometry in determining the reaction outcome
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5084065/
https://www.ncbi.nlm.nih.gov/pubmed/27807509
http://dx.doi.org/10.1021/acscatal.6b00739
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