Regioselective palladium-catalyzed ring-opening reactions of C1-substituted oxabicyclo[2,2,1]hepta-2,5-diene-2,3-dicarboxylates

Palladium-catalyzed ring-opening reactions of C1 substituted 7-oxanorbornadiene derivatives with aryl iodides were investigated. The optimal conditions for this reaction were found to be PdCl(2)(PPh(3))(2), ZnCl(2), Et(3)N and Zn in THF. Both steric and electronic factors played a role in the outcom...

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Autores principales: Edmunds, Michael, Raheem, Mohammed Abdul, Boutin, Rebecca, Tait, Katrina, Tam, William
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2016
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4778517/
https://www.ncbi.nlm.nih.gov/pubmed/26977182
http://dx.doi.org/10.3762/bjoc.12.25
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author Edmunds, Michael
Raheem, Mohammed Abdul
Boutin, Rebecca
Tait, Katrina
Tam, William
author_facet Edmunds, Michael
Raheem, Mohammed Abdul
Boutin, Rebecca
Tait, Katrina
Tam, William
author_sort Edmunds, Michael
collection PubMed
description Palladium-catalyzed ring-opening reactions of C1 substituted 7-oxanorbornadiene derivatives with aryl iodides were investigated. The optimal conditions for this reaction were found to be PdCl(2)(PPh(3))(2), ZnCl(2), Et(3)N and Zn in THF. Both steric and electronic factors played a role in the outcome of the reaction as increasing the steric bulk on the bridgehead carbon decreased the yield. These reactions were found to be highly regioselective, giving only one of the two possible regioisomers in all cases. A diverse collection of novel, highly substituted biphenyl derivatives were obtained.
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spelling pubmed-47785172016-03-14 Regioselective palladium-catalyzed ring-opening reactions of C1-substituted oxabicyclo[2,2,1]hepta-2,5-diene-2,3-dicarboxylates Edmunds, Michael Raheem, Mohammed Abdul Boutin, Rebecca Tait, Katrina Tam, William Beilstein J Org Chem Full Research Paper Palladium-catalyzed ring-opening reactions of C1 substituted 7-oxanorbornadiene derivatives with aryl iodides were investigated. The optimal conditions for this reaction were found to be PdCl(2)(PPh(3))(2), ZnCl(2), Et(3)N and Zn in THF. Both steric and electronic factors played a role in the outcome of the reaction as increasing the steric bulk on the bridgehead carbon decreased the yield. These reactions were found to be highly regioselective, giving only one of the two possible regioisomers in all cases. A diverse collection of novel, highly substituted biphenyl derivatives were obtained. Beilstein-Institut 2016-02-09 /pmc/articles/PMC4778517/ /pubmed/26977182 http://dx.doi.org/10.3762/bjoc.12.25 Text en Copyright © 2016, Edmunds et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Edmunds, Michael
Raheem, Mohammed Abdul
Boutin, Rebecca
Tait, Katrina
Tam, William
Regioselective palladium-catalyzed ring-opening reactions of C1-substituted oxabicyclo[2,2,1]hepta-2,5-diene-2,3-dicarboxylates
title Regioselective palladium-catalyzed ring-opening reactions of C1-substituted oxabicyclo[2,2,1]hepta-2,5-diene-2,3-dicarboxylates
title_full Regioselective palladium-catalyzed ring-opening reactions of C1-substituted oxabicyclo[2,2,1]hepta-2,5-diene-2,3-dicarboxylates
title_fullStr Regioselective palladium-catalyzed ring-opening reactions of C1-substituted oxabicyclo[2,2,1]hepta-2,5-diene-2,3-dicarboxylates
title_full_unstemmed Regioselective palladium-catalyzed ring-opening reactions of C1-substituted oxabicyclo[2,2,1]hepta-2,5-diene-2,3-dicarboxylates
title_short Regioselective palladium-catalyzed ring-opening reactions of C1-substituted oxabicyclo[2,2,1]hepta-2,5-diene-2,3-dicarboxylates
title_sort regioselective palladium-catalyzed ring-opening reactions of c1-substituted oxabicyclo[2,2,1]hepta-2,5-diene-2,3-dicarboxylates
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4778517/
https://www.ncbi.nlm.nih.gov/pubmed/26977182
http://dx.doi.org/10.3762/bjoc.12.25
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