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October 5, 2025Advanced Synthesis & Catalysis2 citations

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

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JCJing CuiYSYizhi SongYLYitong Liu

Key Points

  • The new method achieves efficient C(sp2)–H alkylation using alkyl iodides under mild conditions, enhancing functional group compatibility.
  • Through a sequential hydrogen and halogen atom transfer process, the approach allows late-stage diversification of various heterocycles.
  • The utilization of stable amine-borane adducts provides an accessible route to generating boryl radicals, vital for the reaction.
  • Operational simplicity coupled with the use of ambient air as the oxidant makes this method sustainable and practical.

Abstract

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(sp 2 )–H alkylation of quinoxalin‐2(1 H )‐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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Cite This Study

Cui et al. (2025) studied this question.

synapsesocial.com/papers/68e2537cd6d66a53c24746fahttps://doi.org/10.1002/adsc.70151
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