可见光促进苯并咪唑中未活化烯烃的自由基环化：二氟甲基和芳基二氟甲基取代多环咪唑的合成。

IF 2.2 4区化学 Q2 CHEMISTRY, ORGANIC

Beilstein Journal of Organic Chemistry Pub Date : 2025-01-30 eCollection Date: 2025-01-01 DOI:10.3762/bjoc.21.15

Yujun Pang, Jinglan Yan, Nawaf Al-Maharik, Qian Zhang, Zeguo Fang, Dong Li

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引用次数: 0

摘要

通过可见光促进自由基环化反应，建立了一种高效、环保的合成二氟甲基和芳基二氟甲基取代多环咪唑的方法。该方法采用易获得且价格低廉的CF2HCO2H或PhCF2COOH，以及含未活化烯烃和PhI(OAc)2的苯并并唑作为底物，无需任何碱、金属催化剂、光催化剂或添加剂。共检测了24个样品，所有样品都成功地进行了环化反应，以良好到优异的收率生产目标产物。机理研究表明，该反应通过自由基途径进行。

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Visible-light-promoted radical cyclisation of unactivated alkenes in benzimidazoles: synthesis of difluoromethyl- and aryldifluoromethyl-substituted polycyclic imidazoles.

An efficient and eco-friendly approach for synthesizing difluoromethyl- and aryldifluoromethyl-substituted polycyclic imidazoles was established via a visible-light-promoted radical cyclization reaction. This method employed the readily accessible and inexpensive CF₂HCO₂H or PhCF₂COOH, along with benzimidazoles bearing unactivated alkenes and PhI(OAc)₂ as substrates, and proceeded without the need of any base, metal catalyst, photocatalyst or additive. In total, 24 examples were examined, and all of them successfully underwent cyclization reaction to produce the target products in good to excellent yields. Mechanistic studies revealed that the reaction proceeds via a radical pathway.

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来源期刊

Beilstein Journal of Organic Chemistry 化学-有机化学

CiteScore

4.90

自引率

3.70%

发文量

167

审稿时长

1.4 months

期刊介绍： The Beilstein Journal of Organic Chemistry is an international, peer-reviewed, Open Access journal. It provides a unique platform for rapid publication without any charges (free for author and reader) – Platinum Open Access. The content is freely accessible 365 days a year to any user worldwide. Articles are available online immediately upon publication and are publicly archived in all major repositories. In addition, it provides a platform for publishing thematic issues (theme-based collections of articles) on topical issues in organic chemistry. The journal publishes high quality research and reviews in all areas of organic chemistry, including organic synthesis, organic reactions, natural product chemistry, structural investigations, supramolecular chemistry and chemical biology.