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

doi:10.6023/cjoc202604050

Chinese Journal of Organic Chemistry ›› 2026, Vol. 46 ›› Issue (9): 3338-3355.DOI: 10.6023/cjoc202604050 Previous Articles Next Articles

REVIEW

烯烃碳碳双键氮化断裂重构研究进展

徐瑞麟^a, 石宏伟^a^,^*(), 焦宁^a^,^b^,^c^,^*()

^a 北京大学药学院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全国重点实验上海 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 发布日期:2026-08-03
通讯作者: 石宏伟, 焦宁
基金资助:
国家自然科学基金(22401010); 国家自然科学基金(22293014); 国家自然科学基金(22131002); 及国家重点研发计划(2021YFA1501700)

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

Ruilin Xu^a, Hongwei Shi^a^,^*(), Ning Jiao^a^,^b^,^c^,^*()

^a State Key Laboratory of Natural and Biomimetic Drugs, New Cornerstone Science Laboratory, Chemical Biology Center, School of Pharmaceutical Sciences, Peking University, Beijing 100191
^b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032
^c Laboratory for Synthetic Chemistry and Chemical Biology Limited, Health@InnoHK, Innovation and Technology Commission, Hong Kong 999077

Received:2026-04-29 Revised:2026-07-17 Published:2026-08-03
Contact: Hongwei Shi, Ning Jiao
About author:
Dedicated to the 100th anniversary of the birth of Professor Xikui Jiang.
Supported by:
National Natural Science Foundation of China(22401010); National Natural Science Foundation of China(22293014); National Natural Science Foundation of China(22131002); National Key R&D Program of China(2021YFA1501700)

The carbon-carbon double bond (C=C), 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 C=C 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 C=C bonds. The reaction characteristics, substrate applicability, and mechanisms of different systems are categorized and compared according to the types of nitrogen sources. Further- more, 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

Ruilin 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, 2026, 46(9): 3338-3355.

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Fig. & Tab. 23

Figure 1. Modification and remodeling of olefinic C=C (a) A brief introduction to C=C bond transformations; (b) C=C bond cleavage with carbon insertion; (c) C=C bond cleavage with oxygen insertion; (d) C=C bond cleavage with nitrogen insertion.

Figure 2. TEMPO-catalyzed nitrogenative cleavage of alkenes with TMSN3

Figure 3. Cu-catalyzed nitrogenative cleavage of alkenes with TMSN3

Figure 4. Photosensitized Mn-catalyzed remodeling of alkenes with TMSN3

Figure 5. Plausible mechanisms for Cu- or Mn-catalyzed nitrogenative cleavage of alkenes with TMSN3

Figure 6. NBS-promoted Cu-catalyzed nitrogenative cleavage of alkenes with TMSN3

Figure 7. NBS-promoted Co-catalyzed nitrogenative cleavage of alkenes with TMSN3

Figure 8. Plausible mechanisms for NBS-promoted nitrogenative cleavage of alkenes with TMSN3

Figure 9. Electrochemical nitrogenative cleavage of alkenes with TMSN3

Figure 10. Mn-catalyzed nitrogenative cleavage of alkenes with NH3

Figure 11. Plausible mechanisms for Mn-catalyzed nitrogenative cleavage of alkenes with NH3

Figure 12. PIDA-promoted nitrogenative cleavage of styrenes with NH4HCO3

Figure 13. Plausible mechanism for PIDA-promoted remodeling of styrenes with NH4HCO3

Figure 14. PIFA-promoted nitrogenative cleavage of alkenes with NH2COONH4 or NH4Cl

Figure 15. PIFA-promoted nitrogenative cleavage of alkenes with NH2COONH4 or NH4Cl

Figure 16. Plausible mechanism for PIFA-promoted nitrogenative cleavage of alkenes with NH2COONH4

Figure 17. PIDA-promoted nitrogenative cleavage of silyl-enol-ethers with NH2COONH4 and plausible mechanism

Figure 18. Nitrogenative cleavage of styrenes with NaNO2

Figure 19. Plausible mechanism for nitrogenative cleavage of styrenes with NaNO2

Figure 20. Co-catalyzed nitrogenative cleavage of alkenes with ArONH2 and plausible mechanism

Figure 21. Nitrogenative cleavage of alkenes with triazadienium

Figure 22. Plausible mechanism for nitrogenative cleavage of alkenes with triazadienium

Nitrogen source	Substrate scope	Product	Oxidant	Catalyst
TMSN₃	Conjugated/nonconjugated alkenes	Carboxide along with nitrile	Oxygen	TEMPO/[Cu]/[Mn]/[Co]
Ammonia or ammonium salts	Conjugated/nonconjugated alkenes	Nitrile	PIDF/PIDA/oxygen	MnO_x/catalyst free
Nitrite	Conjugate alkenes only	Benzonitrile	Oxidant free	Catalyst free
Hydroxylamine	Conjugated/nonconjugated alkenes	Oxime ether	Oxidant free	Co_SA—N/C
Triazadienium	Conjugated/nonconjugated alkenes	Diamine	t-BuOCl	Catalyst free

Table 1. Summary for different nitrogenative cleavage reactions using different nitrogen source

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烯烃碳碳双键氮化断裂重构研究进展

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

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