研究论文

铜催化砜基诱导的区域选择性C(sp3)—H键杂芳基化反应

  • 刘慧英 ,
  • 吴中天 ,
  • 李昊天 ,
  • 吴新鑫
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  • 苏州大学材料与化学化工学部 江苏省有机合成重点实验室 江苏苏州 215123
†共同第一作者

收稿日期: 2024-06-22

  修回日期: 2024-07-09

  网络出版日期: 2024-07-25

基金资助

国家自然科学基金(22001185); 江苏省高等学校基础科学(自然科学)研究重大项目(23KJA150007)

Cu-Catalyzed Regioselective Heteroarylation of C(sp³)—H Bond Induce by Sulfonyl Group

  • Huiying Liu ,
  • Zhongtian Wu ,
  • Haotian Li ,
  • Xinxin Wu
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  • Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou, Jiangsu 215123
†These authors contributed equally to this work.

Received date: 2024-06-22

  Revised date: 2024-07-09

  Online published: 2024-07-25

Supported by

National Natural Science Foundation of China(22001185); Natural Science Foundation of the Jiangsu Higher Education Institutions of China(23KJA150007)

摘要

区域选择性碳氢键官能化反应具有良好的原子经济性和步骤经济性, 在复杂分子和天然产物后期修饰中具有很大的应用潜力. 自由基参与的氢原子转移策略由于其高化学选择性和区域选择性近年来备受化学家们的关注. 由于C(sp³)—H键之间的键离解能(BDE)差异相对较小, 烷基自由基参与的氢原子转移反应研究较少. 报道了一种铜催化砜基诱导的区域选择性C(sp³)—H键杂芳基化反应, 该策略利用砜基α位烷基自由基作为分子内攫氢试剂, 在铜催化的条件下实现区域选择性碳氮键的构建.

本文引用格式

刘慧英 , 吴中天 , 李昊天 , 吴新鑫 . 铜催化砜基诱导的区域选择性C(sp3)—H键杂芳基化反应[J]. 有机化学, 2025 , 45(1) : 297 -306 . DOI: 10.6023/cjoc202406034

Abstract

The regioselective carbon-hydrogen bond functionalization reaction in atom- and step-economy holds significant potential for the late-stage elaboration of complex molecules and natural products. In recent years, the hydrogen atom transfer strategy involving radicals has garnered considerable attention from chemists due to its high chemoselectivity and regioselectivity. However, owing to the marginal differences in bond dissociation energies (BDEs) among C(sp³)—H bonds, hydrogen atom transfer reactions mediated by alkyl radicals remain less-developed. A copper-catalyzed sulfone-induced regioselective C(sp³)—H bond heteroarylation reaction was reported. This strategy utilizes the α-alkyl radical of sulfone as an intramolecular hydrogen abstraction reagent, enabling the regioselective formation of carbon-nitrogen bonds under copper catalysis.

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