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光激发丰产金属镍催化卤代芳烃与磺酰胺的C(sp2)-N偶联反应

王力卓a, 刘馨忆a, 宋戈洋*,a, 石晓莉a, 薛东*,a   

  1. a胶体与表面教育部重点实验室, 陕西师范大学 化学化工学院 陕西 西安 710119
  • 收稿日期:2025-11-21 修回日期:2025-12-22
  • 基金资助:
    国家自然科学基金(22171174, 22471150, 22402113)、中央高校基本科研业务费(GK202406026, GK202505023, GK202505026)、陕西省创新能力支撑计划(2023-CX-TD-28)、陕西省化学与生物基础科学研究(22JHZ0027)、陕西省自然科学基金(2024JC-YBQN-0075)、天然药物及仿生药物国家重点实验室开放基金(K202437)、陕西省重点研发计划(2024CY-JJQ-26)资助项目.

Photoexcitation-Enabled C-N Coupling of Aryl Halides with Sulfonamides by Earth-Abundant Nickel Catalyst

Lizhuo Wanga, Xinyi Liua, Geyang Song*,a, Xiaoli Shia, Dong Xue*,a   

  1. aSchool of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an, Shaanxi 710119, China
  • Received:2025-11-21 Revised:2025-12-22
  • Supported by:
    National Natural Science Foundation of China (22171174, 22471150, 22402113), the Fundamental Research Funds for the Central Universities (GK202406026, GK202505023, GK202505026), the Innovation Capability Support Program of Shaanxi (2023-CX-TD-28), the Fundamental Science Research Project of Shaanxi for Chemistry, Biology (22JHZ0027), the Natural Science Foundation of Shaanxi Province (2024JC-YBQN-0075, 2025JC-YBQN-144), the State Key Laboratory of Natural and Biomimetic Drugs (K202437), and the Key Research and Development Program of Shaanxi (2024CY-JJQ-26) .

Sulfonamide compounds have attracted considerable attention in medicinal and synthetic chemistry due to their diverse biological activities, distinctive reactivity, and potential pharmaceutical value. In this work, a mild and efficient method that requires no external photosensitizer was developed to achieve the C(sp²)-N coupling of aryl halides with sulfonamide compounds under irradiation from 390-395 nm LEDs, catalyzed by an earth-abundant nickel catalyst. The method employs readily available nickel as the catalyst and soluble organic amines as bases, offering advantages such as easily accessible starting materials, mild reaction conditions, simple operation, broad substrate scope, and excellent functional-group tolerance. It can also be applied to late-stage modification of bioactive molecules. Even on the gram scale, the reaction maintains high efficiency and yield, providing a practical alternative route for the synthesis of important aryl sulfonamides. Mechanistic studies suggest that the reaction may proceed through a Ni(I)-Ni(III) catalytic cycle.

Key words: Photocatalysis, Nickel Catalysis, Aryl Halides, C-N Coupling Reaction