Arylboronic acid catalyzed C-alkylation and allylation reactions using benzylic alcohols

Susana Estopiñá-Durán; Euan B. Mclean; Liam J. Donnelly; Bryony M. Hockin; James E. Taylor

doi:10.1021/acs.orglett.0c02736

Arylboronic acid catalyzed C-alkylation and allylation reactions using benzylic alcohols

Susana Estopiñá-Durán, Euan B. Mclean, Liam J. Donnelly, Bryony M. Hockin, James E. Taylor

Pure And Applied Chemistry

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Abstract

: The arylboronic acid catalyzed dehydrative Calkylation 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).

Original language	English
Pages (from-to)	7547-7551
Number of pages	5
Journal	Organic Letters
Volume	22
Issue number	19
DOIs	https://doi.org/10.1021/acs.orglett.0c02736
Publication status	Published - 22 Sept 2020

Keywords

arylboronic acid
catalyzed c-alkylation reactions
allylation reactions
benzylic alcohols

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10.1021/acs.orglett.0c02736Licence: CC BY 4.0

Estopiñá-Durán-etal-OL-2020-Arylboronic-acid-catalyzed-C-alkylation-and-allylation-reactions-using-benzylic-alcoholsFinal published version, 1.09 MBLicence: CC BY 4.0

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@article{97eec938365743db8c9a4c110d79407d,

title = "Arylboronic acid catalyzed C-alkylation and allylation reactions using benzylic alcohols",

abstract = ": The arylboronic acid catalyzed dehydrative Calkylation 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).",

keywords = "arylboronic acid, catalyzed c-alkylation reactions, allylation reactions, benzylic alcohols",

author = "Susana Estopi{\~n}{\'a}-Dur{\'a}n and Mclean, \{Euan B.\} and Donnelly, \{Liam J.\} and Hockin, \{Bryony M.\} and Taylor, \{James E.\}",

year = "2020",

month = sep,

day = "22",

doi = "10.1021/acs.orglett.0c02736",

language = "English",

volume = "22",

pages = "7547--7551",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "19",

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TY - JOUR

T1 - Arylboronic acid catalyzed C-alkylation and allylation reactions using benzylic alcohols

AU - Estopiñá-Durán, Susana

AU - Mclean, Euan B.

AU - Donnelly, Liam J.

AU - Hockin, Bryony M.

AU - Taylor, James E.

PY - 2020/9/22

Y1 - 2020/9/22

N2 - : The arylboronic acid catalyzed dehydrative Calkylation 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).

AB - : The arylboronic acid catalyzed dehydrative Calkylation 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).

KW - arylboronic acid

KW - catalyzed c-alkylation reactions

KW - allylation reactions

KW - benzylic alcohols

U2 - 10.1021/acs.orglett.0c02736

DO - 10.1021/acs.orglett.0c02736

M3 - Article

SN - 1523-7060

VL - 22

SP - 7547

EP - 7551

JO - Organic Letters

JF - Organic Letters

IS - 19

ER -

Arylboronic acid catalyzed C-alkylation and allylation reactions using benzylic alcohols

Abstract

Keywords

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