喹啉- 2(1H) -酮与碘化烷基直接C-H功能化的光诱导序序氢和卤素原子转移

IF 4 2区化学 Q2 CHEMISTRY, APPLIED

Advanced Synthesis & Catalysis Pub Date : 2025-10-04 DOI:10.1002/adsc.70151

Jing Cui, Yizhi Song, Yitong Liu, Kaikai Niu, Ling‐Bao Xing, Qingmin Wang

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引用次数: 0

摘要

在温和和可持续的条件下，烷基卤化物的化学选择性活化仍然是碳氢官能化化学中一个持续的问题。提出了一种无金属光诱导顺序氢原子转移（HAT）和卤素原子转移（XAT）方法，该方法利用稳定的胺硼烷加合物原位产生的瞬态硼基自由基。该平台通过协同的HAT/XAT级联，利用易于获取的烷基碘化物和环境空气作为末端氧化剂，促进喹啉- 2(1H) - 1的C(sp2) -H烷基化。该方法具有广泛的底物通用性、较高的区域选择性和良好的官能团相容性，能够在操作简单的条件下实现具有药用意义的杂环化合物的后期多样化。

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Photoinduced Sequential Hydrogen and Halogen Atom Transfer for Direct C–H Functionalization of Quinoxalin‐2(1H)‐ones with Alkyl Iodides

The chemoselective activation of alkyl halides under mild and sustainable conditions continues to pose an ongoing issue in C–H functionalization chemistry. A metal‐free, photoinduced sequential hydrogen atom transfer (HAT) and halogen atom transfer (XAT) method that utilizes transient boryl radicals produced in situ from stable amine‐borane adducts is presented. This platform facilitates effective C(sp2)–H alkylation of quinoxalin‐2(1H)‐ones through a synergistic HAT/XAT cascade, utilizing easily accessible alkyl iodides and ambient air as the terminal oxidant. The approach demonstrates broad substrate generality, elevated regioselectivity, and favorable functional group compatibility, enabling late‐stage diversification of pharmaceutically significant heterocycles under operationally simple conditions.

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来源期刊

Advanced Synthesis & Catalysis 化学-应用化学

CiteScore

9.40

自引率

7.40%

发文量

447

审稿时长

1.8 months

期刊介绍： Advanced Synthesis & Catalysis (ASC) is the leading primary journal in organic, organometallic, and applied chemistry. The high impact of ASC can be attributed to the unique focus of the journal, which publishes exciting new results from academic and industrial labs on efficient, practical, and environmentally friendly organic synthesis. While homogeneous, heterogeneous, organic, and enzyme catalysis are key technologies to achieve green synthesis, significant contributions to the same goal by synthesis design, reaction techniques, flow chemistry, and continuous processing, multiphase catalysis, green solvents, catalyst immobilization, and recycling, separation science, and process development are also featured in ASC. The Aims and Scope can be found in the Notice to Authors or on the first page of the table of contents in every issue.