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Chemoselective Benzylation of Aldehydes Using Lewis Base Activated Boronate Nucleophiles.

ABSTRACT: A benzylation of aldehydes using primary and secondary benzylboronic acid pinacol esters is reported. Activation of the boronic ester with s-butyllithium rendered it nucleophilic toward aldehydes. The activated nucleophile chemoselectively transfers the benzyl group over the s-butyl group, providing excellent yields of the benzylated products. 11B NMR experiments were performed to study the mechnism of this transformation.

SUBMITTER: Hollerbach MR

PROVIDER: S-EPMC6824429 | biostudies-literature | 2018 May

REPOSITORIES: biostudies-literature

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Chemoselective Benzylation of Aldehydes Using Lewis Base Activated Boronate Nucleophiles.

Hollerbach Michael R MR Barker Timothy J TJ

Organometallics 20180427 9

A benzylation of aldehydes using primary and secondary benzylboronic acid pinacol esters is reported. Activation of the boronic ester with s-butyllithium rendered it nucleophilic toward aldehydes. The activated nucleophile chemoselectively transfers the benzyl group over the s-butyl group, providing excellent yields of the benzylated products. 11B NMR experiments were performed to study the mechnism of this transformation. ...[more]

PMID: 31680714

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