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Photocatalyst-, metal- and additive-free regioselective radical cascade sulfonylation/cyclization of benzimidazole derivatives with sulfonyl chlorides induced by visible light
Organic Chemistry Frontiers ( IF 5.4 ) Pub Date : 2022-05-24 , DOI: 10.1039/d2qo00518b
Bin Sun 1 , Hai-Xia Tian 2 , Zhi-Gang Ni 3 , Pan-Yi Huang 2 , Hao Ding 2 , Bing-Qian Li 2 , Can Jin 1, 2 , Chun-Lei Wu 4 , Run-Pu Shen 4
Affiliation  

Herein, an environmentally friendly and practical protocol for the visible-light-triggered regioselective radical cascade sulfonylation/cyclization of unactivated alkenes towards the synthesis of polycyclic benzimidazoles containing the sulfone group has been developed. Notably, the control experiments demonstrated that a radical pathway was involved in this reaction, and a sulfonyl radical center was initially generated via self-homolysis of sulfonyl chloride upon irradiation. Moreover, this protocol features a wide substrate scope, high atom economy, and excellent regioselectivity, and is easy to scale up.

中文翻译:

可见光诱导苯并咪唑衍生物与磺酰氯的无光催化剂、无金属和无添加剂的区域选择性自由基级联磺酰化/环化

在此,开发了一种环境友好且实用的方案,用于未活化烯烃的可见光触发区域选择性自由基级联磺酰化/环化,以合成含有砜基的多环苯并咪唑。值得注意的是,对照实验表明该反应涉及自由基途径,并且磺酰基自由基中心最初是通过磺酰氯在辐照时的自均解产生。此外,该协议具有底物范围广、原子经济性高、区域选择性好、易于放大等特点。
更新日期:2022-05-24
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