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

Susana Estopina-Duran; Euan Mclean; Liam Donnelly; Bryony Hockin; James Taylor

doi:10.1021/acs.orglett.0c02736

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

Susana Estopina-Duran, Euan Mclean, Liam Donnelly, Bryony Hockin, James Taylor

Department of Chemistry

University of St Andrews

Research output: Contribution to journal › Article › peer-review

31 Citations (SciVal)

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Abstract

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).

Original language	English
Pages (from-to)	7547-7551
Journal	Organic Letters
Volume	22
Issue number	19
Early online date	22 Sept 2020
DOIs	https://doi.org/10.1021/acs.orglett.0c02736
Publication status	Published - 2 Oct 2020

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Dehydrative_CC_OL_Revised_2.PDF
© ACM, 2020. This is the author's version of the work. It is posted here by permission of ACM for your personal use. Not for redistribution. The definitive version was published in Org. Lett. 2020, 22, 19, 7547–7551 Publication Date:September 22, 2020 https://doi.org/10.1021/acs.orglett.0c02736
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title = "Arylboronic Acid Catalyzed C-Alkylation and Allylation Reactions Using Benzylic Alcohols",

abstract = "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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AU - Estopina-Duran, Susana

AU - Mclean, Euan

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AU - Hockin, Bryony

AU - Taylor, James

PY - 2020/10/2

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N2 - 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).

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

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

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