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可见光诱导香豆素通过与N-羟基邻苯二甲酰亚胺酯的脱羧偶联实现区域选择性烷基化反应

Visible-Light-Induced Regioselective Alkylation of Coumarins via Decarboxylative Coupling with N-Hydroxyphthalimide Esters.

作者信息

Jin Can, Yan Zhiyang, Sun Bin, Yang Jin

机构信息

College of Pharmaceutical Sciences , Zhejiang University of Technology , Hangzhou 310014 , P. R. China.

Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals , Zhejiang University of Technology , Hangzhou 310014 , P. R. China.

出版信息

Org Lett. 2019 Apr 5;21(7):2064-2068. doi: 10.1021/acs.orglett.9b00327. Epub 2019 Mar 27.

DOI:10.1021/acs.orglett.9b00327
PMID:30916971
Abstract

An efficient photocatalytic decarboxylative 3-position alkylation of coumarins by using alkyl N-hydroxyphthalimide esters as alkylation reagents has been developed. A variety of NHP esters derived from aliphatic carboxylic acids (primary, secondary, and tertiary) has been proved to be tolerated for this decarboxylation process, affording a broad scope of 3-alkylated coumarin derivatives in moderate to excellent yields. This protocol was highlighted by its mild conditions, readily available starting materials, operational simplicity, and wide functional group tolerance.

摘要

已开发出一种高效的光催化脱羧反应,该反应以N-羟基邻苯二甲酰亚胺酯为烷基化试剂,实现了香豆素的3-位烷基化。事实证明,多种源自脂肪族羧酸(伯、仲和叔)的NHP酯可用于此脱羧过程,能以中等至优异的产率得到多种3-烷基化香豆素衍生物。该方法的突出特点是条件温和、起始原料易于获得、操作简便且对官能团的耐受性强。

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