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硼二吡咯亚甲基(BODIPYs)在2,6-位的区域选择性脱羧直接C-H芳基化:一种便捷构建多样化BODIPY库的方法。

Regioselective decarboxylative direct C-H arylation of boron dipyrromethenes (BODIPYs) at 2,6-positions: a facile access to a diversity-oriented BODIPY library.

作者信息

Luo Liang, Wu Di, Li Wei, Zhang Shuai, Ma Yuanhong, Yan Su, You Jingsong

机构信息

Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, and State Key Laboratory of Biotherapy, West China Hospital, West China Medical School, Sichuan University, 29 Wangjiang Road, Chengdu 610064, P. R. China.

出版信息

Org Lett. 2014 Dec 5;16(23):6080-3. doi: 10.1021/ol502883x. Epub 2014 Nov 17.

Abstract

A palladium-catalyzed regioselective decarboxylative direct C-H arylation of boron dipyrromethenes (BODIPYs) at the 2,6-positions has been developed as a late-stage approach to rapidly assemble a diversity-oriented BODIPY library. With the complement of this protocol, the direct C-H arylation of BODIPYs becomes regiocontrollable at α- and β-positions. A new type of indole-fused BODIPY exhibiting bright red/NIR fluorescence with a large molar extinction coefficient (145,500 M(-1) cm(-1)) and a high quantum yield (71%) has been synthesized for the first time.

摘要

已开发出一种钯催化的硼二吡咯亚甲基(BODIPY)在2,6位的区域选择性脱羧直接C-H芳基化反应,作为一种后期方法,可快速构建一个多样化的BODIPY库。通过该方案的补充,BODIPY的直接C-H芳基化在α和β位置变得区域可控。首次合成了一种新型的吲哚稠合BODIPY,其具有亮红色/近红外荧光,摩尔消光系数大(145,500 M(-1) cm(-1))且量子产率高(71%)。

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