苄基硼酸酯对活性酮的亲核加成反应
Nucleophilic Addition of Benzylboronates to Activated Ketones.
作者信息
Hayes Jacob C, Hollerbach Michael R, Barker Timothy J
机构信息
Department of Chemistry and Biochemistry, College of Charleston, Charleston, SC 29424.
出版信息
Tetrahedron Lett. 2020 Feb 13;61(7). doi: 10.1016/j.tetlet.2019.151505. Epub 2019 Dec 16.
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 CFH ketone > CF ketone > aldehyde under these reaction conditions.
摘要
已开发出一种方法，可将苄基硼酸频哪醇酯以良好的产率添加到包括三氟甲基酮在内的活性酮中。发现使用1,4-二氮杂双环[2.2.2]辛烷（DABCO）作为添加剂可提高该反应的速率和效率。在酮与存在第二个羰基（如酯或酰胺）的反应中，观察到对酮具有良好的化学选择性。竞争实验表明，在这些反应条件下，亲电试剂的相对反应活性顺序为：偕氟代酮＞氟代酮＞醛。
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