Pd-Catalyzed (3 + 2) Heterocycloadditions between Alkylidenecyclopropanes and Carbonyls: Straightforward Assembly of Highly Substituted Tetrahydrofurans
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Title: | Pd-Catalyzed (3 + 2) Heterocycloadditions between Alkylidenecyclopropanes and Carbonyls: Straightforward Assembly of Highly Substituted Tetrahydrofurans |
Author: | Verdugo Leal, Felipe Ignacio Concepción Vicente, Eduardo da Rodiño Balboa, Ricardo Calvelo Souto, Martín Mascareñas Cid, José Luis López García, Fernando |
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: | Palladium | Hydrocarbons | Cyclization | Ketones | Catalysts | Alkylidenecyclopropane | Cycloaddition | |
Date of Issue: | 2020 |
Publisher: | American Chemical Society |
Citation: | ACS Catal. 2020, 10, 14, 7710–7718 |
Abstract: | A Pd catalyst made from a Pd(0) source and a bulky biaryl phosphine ligand promotes highly efficient intramolecular (3 + 2) heterocycloadditions between alkylidenecyclopropanes (ACPs) and carbonyls. The annulations provide a straightforward access to fused polycyclic systems featuring β-methylene tetrahydrofuran moieties. DFT data support a pallada–ene process and shed light on the critical role of hemilabile interactions between the Pd center and the bulky biaryl phosphine. Significantly, these Pd(0) catalysts are also effective for promoting intermolecular formal cycloadditions between ACPs and trifluoromethyl ketones, thus providing for a direct entry to chiral tetrahydrofuran moieties (THFs) bearing trifluoromethyl–substituted carbons |
Description: | This document is the Accepted Manuscript version of a Published Work that appeared in final form in ACS Catalysis, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acscatal.0c01827 |
Publisher version: | https://doi.org/10.1021/acscatal.0c01827 |
URI: | http://hdl.handle.net/10347/23209 |
DOI: | 10.1021/acscatal.0c01827 |
E-ISSN: | 2155-5435 |
Rights: | © 2020 American Chemical Society. This article may be used for non-commercial purposes in accordance with ACS Terms and Conditions for Use of Self-Archived Versions |
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