Arylboronic Acid Catalyzed C-Alkylation and Allylation Reactions Using Benzylic Alcohols

[Image: see text] The arylboronic acid catalyzed dehydrative C-alkylation of 1,3-diketones and 1,3-ketoesters using secondary benzylic alcohols as the electrophile is reported, forming new C–C bonds (19 examples, up to 98% yield) with the release of water as the only byproduct. The process is also a...

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Autores principales: Estopiñá-Durán, Susana, Mclean, Euan B., Donnelly, Liam J., Hockin, Bryony M., Taylor, James E.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2020
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8155392/
https://www.ncbi.nlm.nih.gov/pubmed/32959662
http://dx.doi.org/10.1021/acs.orglett.0c02736
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author Estopiñá-Durán, Susana
Mclean, Euan B.
Donnelly, Liam J.
Hockin, Bryony M.
Taylor, James E.
author_facet Estopiñá-Durán, Susana
Mclean, Euan B.
Donnelly, Liam J.
Hockin, Bryony M.
Taylor, James E.
author_sort Estopiñá-Durán, Susana
collection PubMed
description [Image: see text] The arylboronic acid catalyzed dehydrative C-alkylation of 1,3-diketones and 1,3-ketoesters using secondary benzylic alcohols as the electrophile is reported, forming new C–C bonds (19 examples, up to 98% yield) with the release of water as the only byproduct. The process is also applicable to the allylation of benzylic alcohols using allyltrimethylsilane as the nucleophile (12 examples, up to 96% yield).
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spelling pubmed-81553922021-05-28 Arylboronic Acid Catalyzed C-Alkylation and Allylation Reactions Using Benzylic Alcohols Estopiñá-Durán, Susana Mclean, Euan B. Donnelly, Liam J. Hockin, Bryony M. Taylor, James E. Org Lett [Image: see text] The arylboronic acid catalyzed dehydrative C-alkylation of 1,3-diketones and 1,3-ketoesters using secondary benzylic alcohols as the electrophile is reported, forming new C–C bonds (19 examples, up to 98% yield) with the release of water as the only byproduct. The process is also applicable to the allylation of benzylic alcohols using allyltrimethylsilane as the nucleophile (12 examples, up to 96% yield). American Chemical Society 2020-09-22 2020-10-02 /pmc/articles/PMC8155392/ /pubmed/32959662 http://dx.doi.org/10.1021/acs.orglett.0c02736 Text en Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Estopiñá-Durán, Susana
Mclean, Euan B.
Donnelly, Liam J.
Hockin, Bryony M.
Taylor, James E.
Arylboronic Acid Catalyzed C-Alkylation and Allylation Reactions Using Benzylic Alcohols
title Arylboronic Acid Catalyzed C-Alkylation and Allylation Reactions Using Benzylic Alcohols
title_full Arylboronic Acid Catalyzed C-Alkylation and Allylation Reactions Using Benzylic Alcohols
title_fullStr Arylboronic Acid Catalyzed C-Alkylation and Allylation Reactions Using Benzylic Alcohols
title_full_unstemmed Arylboronic Acid Catalyzed C-Alkylation and Allylation Reactions Using Benzylic Alcohols
title_short Arylboronic Acid Catalyzed C-Alkylation and Allylation Reactions Using Benzylic Alcohols
title_sort arylboronic acid catalyzed c-alkylation and allylation reactions using benzylic alcohols
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8155392/
https://www.ncbi.nlm.nih.gov/pubmed/32959662
http://dx.doi.org/10.1021/acs.orglett.0c02736
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