The vinylogous Catellani reaction: a combined computational and experimental study

In the presence of 5 mol% Pd(OAc)(2), 1 equiv. of norbornene, and K(2)CO(3), the reaction of 4-iodo-2-quinolones with tertiary o-bromobenzylic alcohols produced the desired benzopyran-fused 2-quinolones in moderate to high yields. A Catellani-type mechanism involving vinylic C–H cleavage is proposed...

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Autores principales: Yamamoto, Y., Murayama, T., Jiang, J., Yasui, T., Shibuya, M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2017
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5885779/
https://www.ncbi.nlm.nih.gov/pubmed/29675164
http://dx.doi.org/10.1039/c7sc04265e
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author Yamamoto, Y.
Murayama, T.
Jiang, J.
Yasui, T.
Shibuya, M.
author_facet Yamamoto, Y.
Murayama, T.
Jiang, J.
Yasui, T.
Shibuya, M.
author_sort Yamamoto, Y.
collection PubMed
description In the presence of 5 mol% Pd(OAc)(2), 1 equiv. of norbornene, and K(2)CO(3), the reaction of 4-iodo-2-quinolones with tertiary o-bromobenzylic alcohols produced the desired benzopyran-fused 2-quinolones in moderate to high yields. A Catellani-type mechanism involving vinylic C–H cleavage is proposed based on the results of control experiments and density functional theory calculations.
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spelling pubmed-58857792018-04-19 The vinylogous Catellani reaction: a combined computational and experimental study Yamamoto, Y. Murayama, T. Jiang, J. Yasui, T. Shibuya, M. Chem Sci Chemistry In the presence of 5 mol% Pd(OAc)(2), 1 equiv. of norbornene, and K(2)CO(3), the reaction of 4-iodo-2-quinolones with tertiary o-bromobenzylic alcohols produced the desired benzopyran-fused 2-quinolones in moderate to high yields. A Catellani-type mechanism involving vinylic C–H cleavage is proposed based on the results of control experiments and density functional theory calculations. Royal Society of Chemistry 2017-11-30 /pmc/articles/PMC5885779/ /pubmed/29675164 http://dx.doi.org/10.1039/c7sc04265e Text en This journal is © The Royal Society of Chemistry 2018 http://creativecommons.org/licenses/by/3.0/ This article is freely available. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence (CC BY 3.0)
spellingShingle Chemistry
Yamamoto, Y.
Murayama, T.
Jiang, J.
Yasui, T.
Shibuya, M.
The vinylogous Catellani reaction: a combined computational and experimental study
title The vinylogous Catellani reaction: a combined computational and experimental study
title_full The vinylogous Catellani reaction: a combined computational and experimental study
title_fullStr The vinylogous Catellani reaction: a combined computational and experimental study
title_full_unstemmed The vinylogous Catellani reaction: a combined computational and experimental study
title_short The vinylogous Catellani reaction: a combined computational and experimental study
title_sort vinylogous catellani reaction: a combined computational and experimental study
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5885779/
https://www.ncbi.nlm.nih.gov/pubmed/29675164
http://dx.doi.org/10.1039/c7sc04265e
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