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

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 a...

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Bibliographic Details
Published in:Organic letters 2020-10, Vol.22 (19), p.7547-7551
Main Authors: Estopiñá-Durán, Susana, Mclean, Euan B, Donnelly, Liam J, Hockin, Bryony M, Taylor, James E
Format: Article
Language:English
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Letter
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Summary: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).
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c02736