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Nucleophilic Addition of Benzylboronates to Activated Ketones.

ABSTRACT: A method has been developed for the addition of benzylboronic acid pinacol ester to activated ketones including trifluoromethyl ketones in good yields. The use of DABCO as an additive was found to enhance the rate and efficiency of this reaction. In reactions of ketones with a second carbonyl group present such as an ester or amide, good chemoselectivity for the ketone was observed. Competition experiments suggest an electrophile relative reactivity order of CF₂H ketone > CF₃ ketone > aldehyde under these reaction conditions.

SUBMITTER: Hayes JC

PROVIDER: S-EPMC7041909 | biostudies-literature | 2020 Feb

REPOSITORIES: biostudies-literature

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Nucleophilic Addition of Benzylboronates to Activated Ketones.

Hayes Jacob C JC Hollerbach Michael R MR Barker Timothy J TJ

Tetrahedron letters 20191216 7

A method has been developed for the addition of benzylboronic acid pinacol ester to activated ketones including trifluoromethyl ketones in good yields. The use of DABCO as an additive was found to enhance the rate and efficiency of this reaction. In reactions of ketones with a second carbonyl group present such as an ester or amide, good chemoselectivity for the ketone was observed. Competition experiments suggest an electrophile relative reactivity order of CF2H ketone > CF3</su ...[more]

PMID: 32099267

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