Visible-Light-Promoted Radical Cascade Bicyclization to Access Partially Saturated Pyrrolo[2,3-b]pyridines.

IF 3.9 2区化学 Q2 CHEMISTRY, MULTIDISCIPLINARY

Chemistry - A European Journal Pub Date : 2025-04-09 DOI:10.1002/chem.202500787

Guangpeng Yan, Chengyi Jiang, Shangyu Mao, Ting Zou, Siping Wei, Huirong Xia, Bin Chen, Yao Jian, Dong Yi, Ying Xiong

引用次数: 0

Abstract

A visible-light-promoted cascade [2+2+1] bicyclization reaction of N-cyanamide alkenes and activated alkyl bromides has been successfully established. This reaction exhibits mild conditions, metal-free characteristics, and excellent atom- and step-economy, along with environmental friendliness. It demonstrates broad substrate tolerance and scalability to gram-scale synthesis, underscoring its potential for practical applications. Preliminary mechanistic studies suggest that the reaction proceeds through a photoinduced single-electron transfer (SET) process and a 1,5-hydrogen atom transfer (HAT) process mediated by an iminyl radical.

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可见光促进自由基级联双联反应制备部分饱和吡咯[2,3-b]吡啶。

成功地建立了可见光催化n -氰酰胺烯烃与活化的溴化烷基的级联[2+2+1]双环化反应。该反应条件温和，无金属，具有良好的原子经济性和阶梯经济性以及环境友好性。它展示了广泛的底物耐受性和克级合成的可扩展性，强调了其实际应用的潜力。初步的机理研究表明，该反应通过光诱导单电子转移（SET）过程和亚胺基自由基介导的1,5-氢原子转移（HAT）过程进行。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Chemistry - A European Journal 化学-化学综合

CiteScore

7.90

自引率

4.70%

发文量

1808

审稿时长

1.8 months

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