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

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Estopiñá-Durán, Susana and Mclean, Euan B. and Donnelly, Liam J. and Hockin, Bryony M. and Taylor, James E. (2020) Arylboronic acid catalyzed C-alkylation and allylation reactions using benzylic alcohols. Organic Letters, 22 (19). pp. 7547-7551. ISSN 1523-7060 (https://doi.org/10.1021/acs.orglett.0c02736)

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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).

ORCID iDs

Estopiñá-Durán, Susana, Mclean, Euan B., Donnelly, Liam J. ORCID logoORCID: https://orcid.org/0000-0003-3342-4902, Hockin, Bryony M. and Taylor, James E.;
CORE (COnnecting REpositories)