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Nucleophilic Addition of Benzylboronates to Activated Ketones

Jacob C Hayes, Michael R Hollerbach, Timothy J Barker

Tetrahedron Lett. 2020 Feb 13;61(7):10.1016/j.tetlet.2019.151505.

PMID: 32099267

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.

Chemicals Related in the Paper:

Catalog Number Product Name Structure CAS Number Price
AP1218790409 3-(Trifluoromethyl)-1H-pyrazole-4-boronic acid pinacol ester 3-(Trifluoromethyl)-1H-pyrazole-4-boronic acid pinacol ester 1218790-40-9 Price
AP87100285 Benzylboronic acid pinacol ester Benzylboronic acid pinacol ester 87100-28-5 Price
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