Palladium(II)-Catalyzed annulation between ortho-alkenylphenols and allenes. Key role of the metal geometry in determining the reaction outcome
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Title: | Palladium(II)-Catalyzed annulation between ortho-alkenylphenols and allenes. Key role of the metal geometry in determining the reaction outcome |
Author: | Casanova González, Noelia del Rio, Karina P. García Fandiño, Rebeca Mascareñas Cid, José Luis Gulías Costa, Moisés |
Affiliation: | Universidade de Santiago de Compostela. Centro de Investigación en Química Biolóxica e Materiais Moleculares Universidade de Santiago de Compostela. Departamento de Química Orgánica |
Subject: | Allene | Cycloaddition | C-H activation | Oxepine | Palladium | |
Date of Issue: | 2016-04-14 |
Publisher: | American Chemical Society |
Citation: | ACS Catal., 2016, 6 (5), pp 3349–3353 |
Abstract: | 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 |
Publisher version: | http://dx.doi.org/10.1021/acscatal.6b00739 |
URI: | http://hdl.handle.net/10347/14871 |
DOI: | 10.1021/acscatal.6b00739 |
Rights: | © American Chemical Society |
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