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硼二吡咯类化合物的可见光激发实现了其3,5位与重氮盐的自促进自由基芳基化反应。

Visible-Light Excitation of BODIPYs Enables Self-Promoted Radical Arylation at Their 3,5-Positions with Diazonium Salts.

作者信息

Wang Dandan, Cheng Cheng, Wu Qinghua, Wang Jun, Kang Zhengxin, Guo Xing, Wu Hao, Hao Erhong, Jiao Lijuan

机构信息

Laboratory of Functional Molecular Solids, Ministry of Education, School of Chemistry and Materials Science , Anhui Normal University , Wuhu 241000 , China.

Department of Chemical and Chemical Engineering , Hefei Normal University , Hefei 230061 , China.

出版信息

Org Lett. 2019 Jul 5;21(13):5121-5125. doi: 10.1021/acs.orglett.9b01722. Epub 2019 Jun 24.

DOI:10.1021/acs.orglett.9b01722
PMID:31247747
Abstract

A metal- and additive-free photochemical strategy for the direct arylation of boron dipyrromethene dyes (BODIPYs) at their 3,5-positions is reported. The operationally simple approach occurs under illumination by visible light in the absence of any external photoredox catalyst. The chemistry is driven by the singlet excited state (PS*) of BODIPYs upon visible-light absorption while successively triggering the formation of aryl radicals from aryl diazonium salts. Furthermore, a new type of indole-fused BODIPY with NIR absorption has also been synthesized for the first time.

摘要

报道了一种用于硼二吡咯亚甲基染料(BODIPYs)在其3,5位直接芳基化的无金属和无添加剂的光化学策略。该操作简单的方法在可见光照射下且不存在任何外部光氧化还原催化剂的条件下进行。该化学反应由BODIPYs在吸收可见光时的单重激发态(PS*)驱动,同时依次引发芳基重氮盐形成芳基自由基。此外,还首次合成了一种新型的具有近红外吸收的吲哚稠合BODIPY。

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