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Palladium-Catalyzed Oxidative Domino Carbocyclization–Arylation of Bisallenes

[Image: see text] Herein we report a highly efficient and site-selective palladium-catalyzed oxidative carbocyclization–arylation reaction of bisallenes and arylboronic acids under operationally simple conditions for the selective synthesis of cyclohexadiene derivatives. The palladium source and the...

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Autores principales: Volla, Chandra M. R., Bäckvall, Jan-E.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2016
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5065722/
https://www.ncbi.nlm.nih.gov/pubmed/27761298
http://dx.doi.org/10.1021/acscatal.6b02070
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author Volla, Chandra M. R.
Bäckvall, Jan-E.
author_facet Volla, Chandra M. R.
Bäckvall, Jan-E.
author_sort Volla, Chandra M. R.
collection PubMed
description [Image: see text] Herein we report a highly efficient and site-selective palladium-catalyzed oxidative carbocyclization–arylation reaction of bisallenes and arylboronic acids under operationally simple conditions for the selective synthesis of cyclohexadiene derivatives. The palladium source and the solvent proved to be crucial for the selectivity and the reactivity displayed. Interestingly, in the absence of the nucleophile, an oxidative carbocyclization-β-elimination pathway predominates. The reaction conditions are compatible with a wide range of functional groups, and the reaction exhibits broad substrate scope. Furthermore, key information regarding the mechanism was obtained using control experiments and kinetic studies.
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spelling pubmed-50657222016-10-17 Palladium-Catalyzed Oxidative Domino Carbocyclization–Arylation of Bisallenes Volla, Chandra M. R. Bäckvall, Jan-E. ACS Catal [Image: see text] Herein we report a highly efficient and site-selective palladium-catalyzed oxidative carbocyclization–arylation reaction of bisallenes and arylboronic acids under operationally simple conditions for the selective synthesis of cyclohexadiene derivatives. The palladium source and the solvent proved to be crucial for the selectivity and the reactivity displayed. Interestingly, in the absence of the nucleophile, an oxidative carbocyclization-β-elimination pathway predominates. The reaction conditions are compatible with a wide range of functional groups, and the reaction exhibits broad substrate scope. Furthermore, key information regarding the mechanism was obtained using control experiments and kinetic studies. American Chemical Society 2016-08-23 2016-10-07 /pmc/articles/PMC5065722/ /pubmed/27761298 http://dx.doi.org/10.1021/acscatal.6b02070 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 Volla, Chandra M. R.
Bäckvall, Jan-E.
Palladium-Catalyzed Oxidative Domino Carbocyclization–Arylation of Bisallenes
title Palladium-Catalyzed Oxidative Domino Carbocyclization–Arylation of Bisallenes
title_full Palladium-Catalyzed Oxidative Domino Carbocyclization–Arylation of Bisallenes
title_fullStr Palladium-Catalyzed Oxidative Domino Carbocyclization–Arylation of Bisallenes
title_full_unstemmed Palladium-Catalyzed Oxidative Domino Carbocyclization–Arylation of Bisallenes
title_short Palladium-Catalyzed Oxidative Domino Carbocyclization–Arylation of Bisallenes
title_sort palladium-catalyzed oxidative domino carbocyclization–arylation of bisallenes
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5065722/
https://www.ncbi.nlm.nih.gov/pubmed/27761298
http://dx.doi.org/10.1021/acscatal.6b02070
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