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温和且无催化剂的Petasis/脱羧多米诺反应:N-苄基炔丙胺的化学选择性合成

Mild and catalyst-free petasis/decarboxylative domino reaction: chemoselective synthesis of N-benzyl propargylamines.

作者信息

Feng Huangdi, Jia Huihui, Sun Zhihua

机构信息

College of Chemistry and Chemical Engineering, Shanghai University of Engineering Science , 333 Longteng Road, Shanghai 201620, China.

出版信息

J Org Chem. 2014 Dec 5;79(23):11812-8. doi: 10.1021/jo502349a. Epub 2014 Nov 24.

Abstract

Multicomponent domino reactions are attractive for assembling functionalized compounds. To this end, a one-pot catalyst-free chemoselective synthesis of N-benzyl propargylamines is reported with good functional group compatibility. This mild process involves in situ formation of an active amine through Petasis reaction of primary amines, formaldehyde solution, and boronic acids, which reacts with propiolic acids to give product in up to 94% yield via decarboxylative coupling reaction.

摘要

多组分多米诺反应对于组装功能化化合物具有吸引力。为此,报道了一种一锅法无催化剂的N-苄基炔丙胺化学选择性合成方法,该方法具有良好的官能团兼容性。这个温和的过程涉及通过伯胺、甲醛溶液和硼酸的Petasis反应原位形成活性胺,该活性胺与炔丙酸通过脱羧偶联反应反应生成产率高达94%的产物。

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