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DOI: https://doi.org/10.6023/cjoc202604050

综述与进展

烯烃碳碳双键氮化断裂重构研究进展

  • 徐瑞麟 ,
  • 石宏伟 ,
  • 焦宁
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  • a北京大学药学院 天然药物及仿生药物全国重点实验室 新基石科学实验室 北京 100191;
    b中国科学院上海有机化学研究所 金属有机化学国家重点实验室 上海 200032;
    c香港创新科技署 Health@InnoHK 合成化学与化学生物学实验室有限公司 香港 999077

收稿日期: 2026-04-29

  修回日期: 2026-07-17

  网络出版日期: 2026-08-17

基金资助

国家自然科学基金(Nos. 22401010, 22293014 and 22131002)及国家重点研发计划(grant No. 2021YFA1501700)资助项目.

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Recent Advances in Nitrogenative Cleavage and Remodeling of Carbon-Carbon Double Bonds in Alkenes

  • Ruiling Xu ,
  • Hongwei Shi ,
  • Ning Jiao
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  • aState Key Laboratory of Natural and Biomimetic Drugs, New Cornerstone Science Laboratory, Chemical Biology Center, School of Pharmaceutical Sciences, Peking University, Beijing, 100191;
    bState Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 200032;
    cLaboratory for Synthetic Chemistry and Chemical Biology Limited, Health@InnoHK, Innovation and Technology Commission, Hong Kong, 999077

Received date: 2026-04-29

  Revised date: 2026-07-17

  Online published: 2026-08-17

Supported by

NSFC (grant Nos. 22401010, 22293014 and 22131002), the National Key R&D Program of China (grant No. 2021YFA1501700).

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摘要

碳碳双键作为有机分子的基本结构单元,其高效、高选择性转化一直是有机化学研究的核心课题之一。与传统的烯烃官能团修饰相比,直接断裂碳碳双键以实现分子骨架重塑,由于反应惰性高、选择性难以控制,因而极具挑战性,是有机合成领域的前沿方向。其中,氮化断裂反应通过在断裂碳碳双键的同时引入氮原子,为高价值含氮分子的构建提供了新颖且高效的合成策略。近年来,该领域发展迅速,基于不同氮源的反应体系日益多样化,机理研究也逐渐深入。本综述系统总结了近年来烯烃碳碳双键氮断裂化重构的研究进展,按照氮源类型对不同体系的反应特点、底物适用性及反应机理进行了系统梳理与比较,并对该领域当前面临的挑战与未来发展方向进行了展望,以期为碳碳键活化及含氮化合物的高效合成提供参考。

关键词： 烯烃; 碳碳键断裂; 氮化反应; 骨架重构; 含氮化合物

本文引用格式

徐瑞麟 , 石宏伟 , 焦宁 . 烯烃碳碳双键氮化断裂重构研究进展[J]. 有机化学, 0 : 202604050 . DOI: 10.6023/cjoc202604050

Abstract

The carbon-carbon double bond, as a fundamental structural unit of organic molecules, has long been a central research topic in organic chemistry due to the pursuit of its efficient and highly selective transformations. Compared with traditional functionalization of olefins, the direct cleavage of carbon-carbon double bonds to achieve molecular skeleton reconstruction is particularly challenging due to their high inertness and the difficulty in controlling selectivity, representing a cutting-edge direction in organic synthesis. Among these transformations, nitrogenative cleavage reactions, which simultaneously break the inert C=C bond and introduce a nitrogen atom, provide a novel and efficient strategy for constructing high-value nitrogen-containing molecules. In recent years, this field has developed rapidly, with reaction systems based on different nitrogen sources becoming increasingly diverse and mechanistic studies continually deepening. This review systematically summarizes recent research progress in the nitrogenative reconstruction of olefinic carbon-carbon double bonds. The reaction characteristics, substrate applicability, and mechanisms of different systems are categorized and compared according to the types of nitrogen sources. Furthermore, current challenges and future directions in this field are discussed, aiming to provide insights for carbon-carbon bond activation and the efficient synthesis of nitrogen-containing compounds.

Key words： alkene; carbon-carbon bond cleavage; nitrogenation; skeletal remodeling; nitrogen-containing compounds

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