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

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17 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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Data for Arylboronic Acid-Catalyzed C-Alkylation and Allylation Reactions Using Benzylic Alcohols
Estopina-Duran, S. (Creator), Mclean, E. (Creator), Donnelly, L. (Creator), Hockin, B. (Creator) & Taylor, J. (Creator), University of Bath, 17 Sept 2020
DOI: 10.15125/BATH-00892
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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).",

author = "Susana Estopina-Duran and Euan Mclean and Liam Donnelly and Bryony Hockin and James Taylor",

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AU - Estopina-Duran, Susana

AU - Mclean, Euan

AU - Donnelly, Liam

AU - Hockin, Bryony

AU - Taylor, James

PY - 2020/10/2

Y1 - 2020/10/2

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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DO - 10.1021/acs.orglett.0c02736

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JO - Organic Letters

JF - Organic Letters

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

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

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