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

Susana EstopiñáDurán | Zendy; Euan B. McLean | Zendy; Liam J. Donnelly | Zendy; Bryony M. Hockin | Zendy; James E. Taylor | Zendy

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

Author(s) -

Susana EstopiñáDurán,

Euan B. McLean,

Liam J. Donnelly,

Bryony M. Hockin,

James E. Taylor

Publication year - 2020

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.0c02736

Subject(s) - chemistry , alkylation , yield (engineering) , electrophile , nucleophile , catalysis , organic chemistry , medicinal chemistry , materials science , metallurgy

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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