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DOI: https://doi.org/10.6023/cjoc202606023

综述与进展

经过渡金属卡宾中间体的硫叶立德反应研究进展

  • He Weibao ,
  • Yi ,
  • Rongnan ,
  • Wu ,
  • Zhilin ,
  • He ,
  • Weimin
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  • a湖南化工职业技术学院 技术与职业教育研究中心 株洲 412000;
    b湖南警察学院 食药环及毒品检验技术湖南省普通高等学校重点实验室 长沙 410138;
    c南京林业大学 化学工程学院 南京 210037;
    d南华大学 化学化工学院 衡阳 421001

收稿日期: 2026-06-20

  修回日期: 2026-07-20

  网络出版日期: 2026-08-24

基金资助

湖南省自然科学基金(No. 2026JJ90135), 湖南省教育厅科学研究项目(No. 25A0703), 长沙市自然科学基金 (No.104872) 资助项目.

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Research Progress on Reactions of Sulfur Ylides via Metal Carbene Intermediates

  • 何卫保 ,
  • 易荣楠 ,
  • 伍智林 ,
  • 何卫民
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  • aResearch Center for Technical and Vocational Education Studies, Hunan Chemical Vocational Technology College, Zhuzhou 412000;
    bKey Laboratory of Food & Environment & Drug Monitoring and Testing of Universities in Hunan Province, Hunan Police Academy, Changsha 410138;
    cCollege of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, China;
    dSchool of Chemistry and Chemical Engineering, University of South China, Hengyang 421001

Received date: 2026-06-20

  Revised date: 2026-07-20

  Online published: 2026-08-24

Supported by

Hunan Provincial Natural Science Foundation (No. 2026JJ90135), the Scientific Research Fund of Hunan Provincial Education Department (No. 25A0703) and the Changsha Natural Science Foundation (No.104872)

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摘要

硫叶立德是有机合成中极具应用价值的活性中间体, 广泛用于复杂分子、天然产物及药物骨架构建. 过渡金属卡宾是卡宾碳与过渡金属以共价/配位键结合形成的有机金属活性中间体, 中心金属与卡宾碳形成双键结构, 卡宾碳具有高度反应活性. 过渡金属可直接与硫叶立德结合产生金属卡宾中间体, 也可先与重氮化合物等形成金属卡宾再被含硫化合物捕获形成硫叶立德而参与各类反应. 本文系统梳理了2022年以来经过渡金属卡宾中间体的硫叶立德反应研究进展. 按照该类中间体参与的典型转化反应类型, 即环化反应、插入反应、重排反应及其他反应, 详细阐述了其构建策略、反应机理与底物适用性.

关键词： 硫叶立德; 过渡金属; 卡宾; 研究进展

本文引用格式

He Weibao , Yi , Rongnan , Wu , Zhilin , He , Weimin . 经过渡金属卡宾中间体的硫叶立德反应研究进展[J]. 有机化学, 0 : 202606023 . DOI: 10.6023/cjoc202606023

Abstract

Sulfur ylides are highly valuable active intermediates in organic synthesis and are widely employed for the construction of complex molecules, natural products and pharmaceutical skeletons. Transition metal carbenes are organometallic active species formed by the covalent or coordinate bonding between carbene carbons and transition metals. A double bond exists between the central metal and the carbene carbon, which endows the carbene carbon with high reactivity. Transition metals can directly coordinate with sulfur ylides to generate metal carbene intermediates. Alternatively, transition metals first react with diazo compounds or other precursors to form metal carbenes, which are then trapped by sulfur-containing compounds to produce sulfur ylides for subsequent diverse reactions. This paper systematically reviews the research progress of sulfur ylide reactions proceeding via transition metal carbene intermediates since 2022. Classified by typical transformations including cyclization, insertion, rearrangement and other reactions, this article elaborates on their synthetic strategies, reaction mechanisms and substrate scope in detail.

Key words： sulfur ylide; transition metal; carbene; research progress

参考文献

1. (a) Stang, M.; Blum, S. A.,Organometallics 2024, 44, 169;(b) Xu, Y.; Zhang, S.; Huang, D.; Wu, X., Org. Biomol. Chem. 2024, 22, 6443;(c) Yang D.-S.; Chen X.-L.; Wu, A.-X., Org. Chem. Front. 2024, 11,2665; (d) Qian, C.; Zhong, Z.; Xu, Q.; Li, P.; Zhang, C.; Sun, J.,J. Am. Chem. Soc. 2025, 147, 32110;(e) Peng, Q.-H.; Peng, J.; Cai, Y.-L.; Wang, Z.-L.; Yi, R.-N.; Shen, C.; He, W.-M., Acta Chim. Sinica 2025, 83, 1013;, 13862.
2. (a) Xu, Y.-Z.; Han, N.-N.; Diao, X.-Q.; Yuan, J.-W.; Xiao, Y.-M.; Yang, L.-R.; Qu, L.-B.,Acta Chim. Sinica 2026, 84, 521;(b) Liu, Y.-Q.; Chen, W.-J.; Zhao, Z.-Y.; Wang, S.-Q.; Tang, S.-S.; He, W.-M.; Peng, J.-M., Chin. J. Org. Chem. 2025, 45, 3546;(c) Sun, C.; Zhou, Q.; Li, C.-Y.; Wang, L.,Chin. J. Org. Chem. 2024, 44, 1957.
3. (a) Zhang, W.; Zhang, X.; Liu, Z.; Yin, G.; Shen, X.; Song, W.; Zhang, H.; Sivaguru, P.; Bi, X.,Angew. Chem. 2026, 138, e7690506;(b) Lv, J.; Liu, Y.; Liu, X.; Si, Z.; Li, X.; Chen, Y.; Liu, L., Chin. J. Org. Chem. 2026, 46, 2409;(c) Zhang, Q.; Shao, Y.-B.; Tian, H.; Wang, Y.-F.; Cai, Z.-X.; Jiang, J.-W.; Shi, C.-Y.; Meng, F.; Xue, X.-S.; Yin, L.,J. Am. Chem. Soc. 2026, 148, 6674;(d) Zhang, C.-G.; Shi, S.-L., J. Am. Chem. Soc. 2026, 148, 5892;, 2125.
4. (a) Phelps, R.; Orr-Ewing, A. J.,J. Am. Chem. Soc. 2022, 144, 9330;(b) Liu Z.; Sivaguru P.; Zanoni G.; Bi, X., Acc. Chem. Res. 2022, 55,1763; (c) Shan, C.; Zeng, Y.; Luo, X.; Yi, Y.; Bai, R.,ChemPhysChem 2025, 26, e202500566;(d) He, M.; Hu, C. P.; Wei, R.; Wang, X. F.; Liu, L. L., Chem. Soc. Rev. 2024, 53, 3896.
5. Jin Z.; Yu T.; Wang H.; Jia P.; Huang Y.,Org. Chem. Front. 2024, 11, 6573.
6. (a) Jiang, D.; Yang, C.; Man, X.; Li, X.; Wang, H.; Song, Y.; Qi, Z.,Org. Biomol. Chem. 2026, 24, 152;(b) Yang, W.; Zhang, Z.; Yang, Z.; Chen, X.; Qiao, L.; Chen, X.; Sun, K.; Qu, L.; Yu, B., J. Org. Chem. 2025, 90, 16403;, 6109;(d) Qiao L.; Zhang Z.; Wu Y.; Sun K.; Li X.; Chen X.; Qu L.; Yu, B., Org. Lett. 2026, 28,9077; (e) Li, T.; Ouyang, W.; Yi, R.-N.; Tang, Y.-C.; Yang, Z.; Wu, C.; He, W.-M.,Chin. J. Org. Chem. 2026, 46, 1668;(f) Zeng, Y.-Y.; Jiang, J.; Wen, Y.-C.; Zhuang, C.-L.; Ou, L.-J.; Yang, Z.; Zhu, H.-T.; Wang, Z.-L.; He, W.-M., Chin. Chem. Lett. 2025, 111776;2025, 111402.
7. Singh Davas, D.; Bhardwaj, S.; Kumar Vishwakarma, R.; Vaitla, J.,Eur. J. Org. Chem. 2024, 27, e202400712.
8. Chen X.-P.; Wang Q.-L.; Hou X.-H.; Wang C.-C.; Ma Z.-W.; Zhang J.-Y.,Chin. J. Org. Chem. 2025, 45, 2796.
9. Hu R.; Miao C.-B.; Guo W.; Sun J.,Synlett 2025, 36, 1338.
10. Ammara; Mansha, A.; Khan, S. G.; Zahoor, A. F.; Saif, M. J.; Parveen, B.; Saeed, M. A.; Chaudhry, A. R.; Irfan, A.; Abbas, M.,RSC Adv. 2025, 15, 37125.
11. Li X.; Zhang Z.-Q.; Lin Z.-Y.; Yao J.-C.; Li X.-Y.; Li Q.-Q.; Xuan J.,Chin. J. Org. Chem. 2026, 46, 1376.
12. Davas D. S.; Gopalakrishnan D. K.; Vaitla J.,Chem. Commun. 2026, 62, 4693.
13. Xing Y.; Fang Y.; Shiri F.; Lin Z.; Chen J.; Wang Z.; Huang Y.,Nat. Commun. 2025, 16, 8416.
14. Timmann S.; Wu T.-H.; Golz C.; Alcarazo M.,Chem. Sci. 2024, 15, 5938.
15. Yang F.; Fan X.-M.; Yao X.-J.; Mi R.-J.; Yu S.-J.; Li X.-W.; Xiao J.,Chin. J. Org. Chem. 2025, 45, 331.
16. (a) He, Y.; Huang, Z.; Wu, K.; Ma, J.; Zhou, Y.-G.; Yu, Z.,Chem. Soc. Rev. 2022, 51, 2759;(b) Kubiak, R. W., II; Tracy, W. F.; Alford, J. S.; Davies, H. M. L.,J. Org. Chem. 2022, 87, 13517.
17. Zhou G.; Guo Z.; Shen X.,Angew. Chem. 2023, 135, e202217189.
18. (a) Li, L.; Chen, B.; Chen, J.; Huang, Y.,Angew. Chem. Int. Ed. 2020, 59, 20904;(b) Chen, B.; Li, L.; Chen, J.; Huang, Y., Adv. Synth. Catal. 2022, 364, 30.
19. Li L.; Mi C.; Huang G.; Huang M.; Zhu Y.; Ni S. F.; Wang Z.; Huang Y.,Angew. Chem. Int. Ed. 2023, 62, e202312793.
20. (a) Yan, D.; He, W.-B.; Tang, Y.-C.; Xin, C.; Yang, Z.; Chen, X.,Chin. J. Org. Chem. 2026, 46, 2327;(b) Zeng Z.; Zhao F.; Zhong H.; Yang Z.; Wei H.; Ji S.; Yu M.; Cai, J., J. Org. Chem. 2025, 90, 15345; (c) Peng M.; Jiang J.; Wang Y.-H.; Li T.; Yang Z.; Zhu H.-T.; He, W.-M., J. Org. Chem. 2025, 90, 18255; (d) Lu J.-J.; Zhang Z.-T.; Ou L.-J.; Jiang D.-F.; Tang Y.; Peng J.-M.; He, W.-M., J. Org. Chem. 2026, 91,5577; (e) Tang, Y.; Huang, J.; Liang, J.; Long, N.; Liu, J.; Yin, Q.; Jiang, D.-F.; Zhu, H.-T.; He, W.-M.,J. Org. Chem. 2026, 91, 6440;(f) Song, H.-K.; Yang, H.-B.; Jing, J.; Li, H.-C.; Sun, K.; Yang, Z.; Li, H.-J.; Chen, X.; Qu, L.; Yu, B., J. Org. Chem. 2026, 91, 6840.
21. Wei J.; Zou W.-X.; Hu Q.; Bao M.-Z.; Shen D.-T.; Xiao L.; Song J.-L.; Liu X.; Zhang S.-S.,Org. Chem. Front. 2024, 11, 3234.
22. Zou W.-X.; Hu Q.; Shen D.-T.; Wu W.-R.; Wei J.; Yang Z.-F.; Bao M.-Z.; Liu X.; Zhang S.-S.,Org. Lett. 2024, 26, 5811.
23. Zhang S.-S.; Wei J.; Hu Q.; Yang Z.-F.; Zou W.-X.; Shen D.-T.; Bao M.-Z.; Liu X.,Org. Lett. 2025, 27, 3709.
24. Wu H.; Xu Y.; Lin A.; Wang Z.; Chen H.; Zhu X.; Gao Y.; Su L.,Nat. Commun. 2024, 15, 10207.
25. Su J.; Huang M.; Yan Z.; Tang S.; Zhang X.; Sun J.,Org. Lett. 2024, 26, 9592.
26. Liu X.; Liu L.-G.; Chen C.-M.; Li X.; Xu Z.; Lu X.; Zhou B.; Ye L.-W.,Angew. Chem. Int. Ed. 2023, 62, e202216923.
27. Hao Y.-D.; Lin Z.-Q.; Guo X.-Y.; Liang J.; Luo C.-K.; Wang Q.-T.; Guo L.; Wu Y.,Chin. Chem. Lett. 2024, 35, 108834.
28. Cribbs C.; Combs J. R.; Gevirtzman V.; O’Malley, C.; Van Vranken, D. L.,Org. Lett. 2025, 27, 3964.
29. Luo C.; Lin Z.; Hao Y.; Jia P.; Lai R.; Guo L.; Yao Y.; Wu Y.,Eur. J. Org. Chem. 2023, 26, e202300690.
30. Meher K. B.; Bankar O. S.; Mukherjee H.; Bhat R. G.,Chem. Asian J. 2025, 20, e00702.
31. Wang J.; Li Q.-Y.; Wang S.-S.; Wu X.-Y.; Li X.; Liu P.-N.,Org. Lett. 2023, 25, 703.
32. Ma J.; Liu X.-S.; Huang X.; Si Z.-Y.; Liu L.,J. Org. Chem. 2024, 89, 11003.
33. Pan S.; Sk M. S.; Sanyal B.; Roy L.; Samanta R.,ACS Catal. 2024, 14, 18419.
34. Gopalakrishnan D. K.; Bhardwaj S.; Kumar S.; Karmakar T.; Vaitla J.,Chem. Commun. 2024, 60, 3846.
35. (a) Hou, J.-C.; Cai, W.; Ji, H.-T.; Ou, L.-J.; He, W.-M.,Chin. Chem. Lett. 2025, 36, 110469;(b) Song, H.-Y.; Jiang, J.; Song, Y.-H.; Zhou, M.-H.; Wu, C.; Chen, X.; He, W.-M., Chin. Chem. Lett. 2024, 35, 109246;, 5862;(d) Cui H.; Qiao X.; Shi T.; Wei W.; Yue H.; Wang Z.; Ma Z.; Yang, Z., Chem. Commun. 2025, 61, 17890; (e) Cui H.; Ma Z.; Yue H.; Xia H.; Wei W.; Yang Z.; Wang Z.; Yi, D., J. Org. Chem. 2025, 90, 18092; (f) Peng Q.-H.; Cai Y.-L.; Dai H.; Zhuang C.-L.; Wang S.-H.; Yang Z.; Wang Z.-L.; Jiang J.; He, W.-M., J. Org. Chem. 2025, 90, 14786; (g) Huang J.; Li R.; Lv Y.; Jia F.; Yue H.; Yang Z.; Wang Z.; Wei W.; Yi, D., J. Org. Chem. 2025, 90, 14805; (h) Yang Z.; Yue H.; Ma C.; Jian Y.; Wei W.; Yi, D., J. Org. Chem. 2026, 91,4460; (i) Zhong, H.; Xing, Z.; Huang, H.; Yang, Z.; Wei, H.; Yu, M.; Cai, J.,J. Org. Chem. 2026, 91, 5651;(j) Wang, Q. L.; He, C. D.; Huang, H.; Yin, L.; Jiang, D. F.; Wei, H.; Hu, X. M.; Yu, M.; Cai, J., Adv. Synth. Catal. 2026, 368, e70579.
36. Sha H.; Qian Y.; Yang X.; Dong K.; Xu X.; Hu W.,Org. Biomol. Chem. 2022, 20, 8223.
37. Bao W.; Wang X. J.; Wang S. H.; Chen S. W.; Liu H. H.; Xiang S. H.; Tan B.,Angew. Chem. Int. Ed. 2024, 63, e202412508.
38. (a) Ishida, S.; Toyooka, T.; Tamura, T.; Abe, T.; Akasaka, N.; Iwamoto, T.,Chem. Eur. J. 2024, 31, e202403847;(b) Shorokhov, V. V.; Chabuka, B. K.; Nikolaeva, A. A.; Zhokhov, S. S.; Andreev, I. A.; Ratmanova, N. K.; Trushkov, I. V.; Ivanova, O. A.; Alabugin, I. V., Org. Chem. Front. 2025, 12, 6852;(c) Zhang, J. W.; Zhang, Y.-C.; Huang, Y.,Angew. Chem. Int. Ed. 2025, 64, e202413102.
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