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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...
Autores principales: | , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American
Chemical Society
2016
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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. |
format | Online Article Text |
id | pubmed-5065722 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2016 |
publisher | American
Chemical Society |
record_format | MEDLINE/PubMed |
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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