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0 202604050

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

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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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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

Cite this article

Ruiling Xu , Hongwei Shi , Ning Jiao . Recent Advances in Nitrogenative Cleavage and Remodeling of Carbon-Carbon Double Bonds in Alkenes[J]. Chinese Journal of Organic Chemistry, 0 : 202604050 . DOI: 10.6023/cjoc202604050

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