Nucleophilic addition of benzylboronates to activated ketones

TETRAHEDRON LETTERS

卷:61

Article

Hayes, Jacob C.¹  Hollerbach, Michael R.¹  Barker, Timothy J.¹ 

[1] Coll Charleston, Dept Chem & Biochem, Charleston, SC 29424 USA

关键词: Boron;    Trifluoromethyl ketone;    Alkylboronic esters;    Lewis base;   

DOI  :  10.1016/j.tetlet.2019.151505

来源: Elsevier

【 摘 要 】

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. (C) 2019 Elsevier Ltd. All rights reserved.

【 授权许可】

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