Research Progress in Catalytic Asymmetric Electrophilic Disulfuration Reactions

doi:10.6023/cjoc202607014

Chinese Journal of Organic Chemistry

REVIEW

催化不对称亲电二硫化反应的研究进展

李泽龙^a, 柯华^b,*, 陈志敏^a,c,*

^a上海交通大学化学化工学院上海市手性药物分子工程重点实验室上海 200240;
^b萍乡大学环保材料与装备工程技术研究中心, 萍乡 337055;
^c上海化工研究院有限公司聚烯烃催化技术与高性能材料全国重点实验室上海 200062

收稿日期:2026-07-15 修回日期:2026-08-11
基金资助:
国家自然科学基金(No. 22471158)、化学生物协同物质创制全国重点实验室自主课题(No. sklscbs202562)、聚烯烃催化技术与高性能材料全国重点实验室专项资金(No. SKLZX-2025-10)资助项目.

Research Progress in Catalytic Asymmetric Electrophilic Disulfuration Reactions

Li Ze-Long^a, Ke Hua^b,*, Chen Zhi-Min^a,c,*

^a Shanghai Key Laboratory of Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai, 200240;
^b Engineering Technology Research Center for Environmental Protection Materials, Pingxiang University, Pingxiang, 337055;
^c State Key Laboratory of Polyolefins and Catalysis, Shanghai Research Institute of Chemical Industry Co., Ltd., Shanghai, 200062

Received:2026-07-15 Revised:2026-08-11
Contact: *E-mail: kehua_pxu@163.com, chenzhimin221@sjtu.edu.cn
Supported by:
National Natural Science Foundation of China (No. 22471158), autonomous Project of State Key Laboratory of Synergistic Chem-Bio Synthesis (No. sklscbs202562), the project of State Key Laboratory of Polyolefins and Catalysis (No. SKLZX-2025-10).

Disulfides are widely used in life sciences, medicinal chemistry, and functional materials, and also serve as important intermediates in the synthesis of organosulfur compounds. Among them, chiral disulfides have shown significant potential in chiral pharmaceuticals and asymmetric catalysis, making their efficient construction an important yet challenging task in synthetic chemistry. Catalytic asymmetric electrophilic disulfuration provides a direct and efficient approach to chiral disulfides, featuring high catalytic efficiency and operational simplicity. In recent years, catalytic asymmetric electrophilic disulfuration strategies based on different electrophilic disulfurating reagents have begun to emerge, enabling the enantioselective synthesis of structurally diverse disulfides. This review classifies these reactions according to the types of electrophilic disulfurating reagents and summarizes the structural features of these reagents, their substrate compatibility, the origins of enantioselectivity, and the further transformations of the resulting chiral disulfides. Finally, the current challenges in this field are discussed, and future development prospects are outlined.

Key words: disulfuration, electrophilic reaction, asymmetric catalysis

Cite this article

Li Ze-Long, Ke Hua, Chen Zhi-Min. Research Progress in Catalytic Asymmetric Electrophilic Disulfuration Reactions[J]. Chinese Journal of Organic Chemistry, doi: 10.6023/cjoc202607014.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Wollaston, W. H. Phil. Trans. R. Soc.1810, 100, 223-230.
[2] Wedemeyer W. J.; Welker E.; Narayan M.; Scheraga H. A. Biochemistry2000, 39, 4207-4216.
[3] Bechtel T. J.; Weerapana E. Proteomics2017, 17, 1600391.
[4] Góngora-Benítez M.; Tulla-Puche J.; Albericio F. Chem. Rev.2014, 114, 901-926.
[5] Chang S.-G.; Choi K.-D.; Jang S.-H.; Shin H.-C. Mol. Cells2003, 16, 323-330.
[6] Fass D.; Thorpe C. Chem. Rev.2018, 118, 1169-1198.
[7] Brülisauer L.; Gauthier M. A.; Leroux, J.-C. J. Control. Release2014, 195, 147-154.
[8] Zhang Q.; Deng Y.-X.; Luo H.-X.; Shi C.-Y.; Geise G. M.; Feringa B. L.; Tian H.; Qu, D.-H. J. Am. Chem. Soc.2019, 141, 12804-12814.
[9] Tu, J.-L. Org. Biomol. Chem.2024, 22, 9165-9178.
[10] Mukaiyama T.; Takahashi K. Tetrahedron Lett.1968, 9, 5907-5908.
[11] Huang P.; Wang P.; Tang S.; Fu Z.; Lei, A. Angew. Chem. Int. Ed.2018, 57, 8115-8119.
[12] Li H.; Peng M.; Li J.; Wang L.; Do H.; Ni K.; Wang M.; Yuan Z.; Zhao T.; Zhang X.; Zhang X.; Hu Z.; Ren F.; An J. Nat. Commun.2024, 15, 8325.
[13] Harpp D. N.; Ash D. K.; Back T. G.; Gleason J. G.; Orwig B. A.; VanHorn W. F.; Snyder, J. P. Tetrahedron Lett.1970, 11, 3551-3554.
[14] Harpp D.; Back, T. J. Org. Chem.1971, 36, 3828-3829.
[15] Gao W.-C.; Feng K.; Tian J.; Zhang J.; Chang H.-H.; Jiang, X. Chin. Chem. Lett.2023, 34, 107587.
[16] Yu Q.; Bai L.; Jiang, X. Angew. Chem. Int. Ed.2023, 62, e202314379.
[17] Yuan T.; Chen X.-Y.; Ji T.; Yue H.; Murugesan K.; Rueping M. Chem. Sci.2024, 15, 15474-15479.
[18] Arisawa M.; Yamaguchi, M. J. Am. Chem. Soc.2003, 125, 6624-6625.
[19] Ong C. L.; Titinchi S.; Juan J. C.; Khaligh, N. G. Helv. Chim. Acta2021, 104, e2100053.
[20] Xiao X.; Feng M.; Jiang, X. Angew. Chem. Int. Ed.2016, 55, 14121-14125.
[21] Zou J.; Chen J.; Shi T.; Hou Y.; Cao F.; Wang Y.; Wang X.; Jia Z.; Zhao Q.; Wang Z. ACS Catal.2019, 9, 11426-11430.
[22] Wang F.; Chen Y.; Rao W.; Ackermann L.; Wang S.-Y. Nat. Commun.2022, 13, 2588.
[23] Chen X.; Shao W.; Deng G.-J. ACS Catal.2024, 14, 6451-6461.
[24] Li W.; Wei H.; Wang B.; He X.; Jiang Y.; Nie M.; Yan H.; Hu Z.; Gao Q.; Qu S.; Wang, X. Angew. Chem. Int. Ed.2025, 64, e202424209.
[25] Tian Q.; Li, Y. Angew. Chem. Int. Ed.2023, 62, e202302861.
[26] Dong Q.-R.; Wang Y.-S.; Zhang J.; Chang H.-H.; Tian J.; Gao W.-C. ACS Catal.2024, 14, 18237-18246.
[27] Wu Z.; Pratt, D. A. J. Am. Chem. Soc.2020, 142, 10284-10290.
[28] Zhang J.; Studer A. Nat. Commun.2022, 13, 3886.
[29] Brooker L. G. S.; Child R.; Smiles, S. J. Chem. Soc.1927, 130, 1384-1388.
[30] Wang W.; Lin Y.; Ma Y.; Tung C.-H.; Xu Z. Org. Lett.2018, 20, 3829-3832.
[31] Zhang Z.; Lao T.; Deng L.; Zhang C.; Liu J.; Fu M.; Su Z.; Yu Y.; Cao H. Org. Lett.2022, 24, 7222-7226.
[32] Yu Y.; Chen J.; Huang M.; Jiang Y.; Zhou X.; Wang J.; Li J.; Cao, H. J. Org. Chem.2024, 89, 3590-3596.
[33] Wang D.; Li W.; Shi K.; Pan, Y. J. Org. Chem.2023, 88, 2550-2556.
[34] Asanuma H.; Kanemoto K. Org. Lett.2024, 26, 438-443.
[35] Xiao X.; Xue J.; Jiang X.Nat. Commun. 2018, 9, 2191.
[36] Zhang S.-S.; Xue J.; Gu Q.; Jiang X.; You, S.-L. Org. Biomol. Chem.2021, 19, 8761-8771.
[37] Kanemoto K.; Furuhashi K.; Morita Y.; Komatsu T.; Fukuzawa S.-I. Org. Lett.2021, 23, 1582-1587.
[38] Asanuma H.; Kanemoto K.; Watanabe T.; Fukuzawa, S.-I. Angew. Chem. Int. Ed.2023, 62, e202219156.
[39] Xue J.; Jiang X. Nat. Commun.2020, 11, 4170.
[40] Yu Q.; Zhang X.; Jiang, X. Angew. Chem. Int. Ed.2024, 63, e202408158.
[41] Yu Q.; Jiang, X. Chem. Eur. J.2025, 31, e202404029.
[42] Gong K.; Zhou Y.; Jiang X. Green Chem.2021, 23, 9865-9869.
[43] Denmark S. E.; Rossi S.; Webster M. P.; Wang, H. J. Am. Chem. Soc.2014, 136, 13016-13028.
[44] Denmark S. E.; Hartmann E.; Kornfilt D. J. P.; Wang H. Nat. Chem.2014, 6, 1056-1064.
[45] Matviitsuk A.; Panger J. L.; Denmark, S. E. Angew. Chem. Int. Ed.2020, 59, 19796-19819.
[46] Doraghi F.; Aledavoud S. P.; Ghanbarlou M.; Larijani B.; Mahdavi, M. Beilstein J. Org. Chem.2023, 19, 1471-1502.
[47] Li Z.-L.; Huo Y.-X.; Gao Q.-S.; Ding T.-M.; Chen, Z.-M. Angew. Chem. Int. Ed.2025, 64, e202515017.
[48] Zhang X.-Y.; Zhu D.; Cao R.-F.; Huo Y.-X.; Ding T.-M.; Chen Z.-M. Nat. Commun.2024, 15, 9929.
[49] Zhu D.; Mu T.; Li Z.-L.; Luo H.-Y.; Cao R.-F.; Xue X.-S.; Chen, Z.-M. Angew. Chem. Int. Ed.2024, 63, e202318625.
[50] Luo H.-Y.; Li Z.-H.; Zhu D.; Yang Q.; Cao R.-F.; Ding T.-M.; Chen, Z.-M. J. Am. Chem. Soc.2022, 144, 2943-2952.
[51] Xie Y.-Y.; Chen Z.-M.; Luo H.-Y.; Shao H.; Tu Y.-Q.; Bao X.; Cao R.-F.; Zhang S.-Y.; Tian, J.-M. Angew. Chem. Int. Ed.2019, 58, 12491-12496.
[52] Gao W.-C.; Tian J.; Shang Y.-Z.; Jiang X. Chem. Sci.2020, 11, 3903-3908.
[53] Yu Q.; Bai L.; Jiang, X. Angew. Chem. Int. Ed.2023, 62, e202314379.
[54] Miao K.; Fu B.; Bai L.; Li C.; Jiang, X. Natl. Sci. Rev.2025, 12, nwaf406.
[55] Gao W.-C.; Liu J.; Jiang, X. Org. Chem. Front.2021, 8, 1275-1279.
[56] Zhang Q.; Li Y.; Zhang L.; Luo, S. Angew. Chem. Int. Ed.2021, 60, 10971-10976.
[57] Huo Y.-X.; Cao R.-F.; Huang J.; Li Z.-L.; Wei Z.-W.; Zhu D.; Chen, Z.-M. Angew. Chem. Int. Ed.2025, 64, e202503815.
[58] Zhou J.; Chen Z.; Nie M.; Li W.; Tong W.-Y.; Wei H.; Yan H.; Gao Q.; Qu S.; Wang X. Chem. Commun.2025, 61, 7329-7332.
[59] Zhang X.; Jiang, X. Chin. J. Org. Chem.2026, 46, DOI: 10.6023/cjoc202604034 (in Chinese).
(张象金,姜雪峰,有机化学,2026, 46, DOI: 10.6023/cjoc202604034.)
[60] Zhang X.; Bai L.; Li C.; Jiang, X. J. Am. Chem. Soc.2026, 148, 12793-12804.

催化不对称亲电二硫化反应的研究进展

Research Progress in Catalytic Asymmetric Electrophilic Disulfuration Reactions

PDF

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Haoyu Zheng, Chuan-Ying Li, You-Yun Zhou. Progress on Transition-Metal-Catalyzed Asymmetric Synthesis of Chiral Tertiary Alkyl Ethers via C—O Bond Formation [J]. Chinese Journal of Organic Chemistry, 2026, 46(8): 2892-2925.
[2]	Song-Yao Chen, Xue Feng, Man-Su Tu, Wen-Juan Hao, Bo Jiang. Ni(II)/Bisimidazoline-Catalyzed Asymmetric Higher-Order (5+3) Annulation for the Construction of Saddle-Shaped Eight-Membered Bridged Biaryls with Concurrent Central and Axial Chirality [J]. Chinese Journal of Organic Chemistry, 2026, 46(7): 2796-2807.
[3]	Kangyu Xiong, Zhan Lu. Research Progress in Transition Metal-Catalyzed Asymmetric Hydroboration of 1,1-Disubstituted Alkenes [J]. Chinese Journal of Organic Chemistry, 2026, 46(7): 2493-2510.
[4]	Kai-Kai Zhao, Run-Qi Fan, Guo-Qiang Lin, Chen-Guo Feng. Synthesis of tert-Butyl Sulfoxide-Oxazoline Ligands and Their Application in Palladium-Catalyzed Asymmetric Allylic Alkylation [J]. Chinese Journal of Organic Chemistry, 2026, 46(6): 2458-2463.
[5]	Chao Zhang, Zhou Luo, Shen Zhao, An Shen, Guoqiang Yang, Yuanyuan Liu. Constructing Chiral Indanes by a Ligand Relay-Enabled Pd-Catalyzed Asymmetric [4+1] Annulation via Carbene Insertion/Tsuji-Trost Cascade [J]. Chinese Journal of Organic Chemistry, 2026, 46(6): 2431-2441.
[6]	Yun Liao, Lijuan Tang, Yingtong Zong, Daohong Yu. Recent Progress in Ruthenium-Catalyzed Asymmetric Functionalization of C(sp²)—H Bonds [J]. Chinese Journal of Organic Chemistry, 2026, 46(5): 1795-1812.
[7]	Jian Shen, Yanbo Wang, Zhengxing Wu, Defeng Xu, Wanbin Zhang. Asymmetric Catalytic Synthesis of α,β-Unsaturated γ-Lactone and γ-Lactam [J]. Chinese Journal of Organic Chemistry, 2025, 45(8): 2637-2659.
[8]	Yiming Du, Junsong Jia, Yulong Li, Wei Shu. Recent Progress on Catalytic Synthesis of Enantioenriched α-Arylated Ketones [J]. Chinese Journal of Organic Chemistry, 2025, 45(6): 1838-1870.
[9]	Lei Su, Xi Yang, Jie Yan, Yuanli Jiang, Lijuan Chen, Qingshu Zheng, Jiawang Liu. Recent Advances in Asymmetric Carbonylative Cross-Coupling Reactions [J]. Chinese Journal of Organic Chemistry, 2025, 45(6): 2007-2047.
[10]	Shuang Wang, Yangjie Mao, Shaojie Lou, Danqian Xu. Recent Advances in Asymmetric C—H Bond Functionalization Using Oxidizing Directing Groups [J]. Chinese Journal of Organic Chemistry, 2025, 45(6): 1961-1994.
[11]	Mengyao Tang, Xiaoyu Yang. Advances on Chiral Phosphoric Acid Catalyzed Asymmetric Electrophilic Amination Reactions [J]. Chinese Journal of Organic Chemistry, 2025, 45(6): 1785-1818.
[12]	Chenyang Jiang, Yanli Yin, Zhiyong Jiang. Advances in Photoenzyme-Catalyzed Asymmetric Radical Addition Reactions [J]. Chinese Journal of Organic Chemistry, 2025, 45(5): 1614-1633.
[13]	Xiu-Xiu Qiao, Qian Li, Shi'na Zhao, Ruiqi Wei, Tao Ma, Yong-Hui He, Xiao-Jing Zhao. Research Progress in Asymmetric Synthesis of C2 Chiral Indolin-3-ones Involving 2-Substituted-3H-indol-3-ones [J]. Chinese Journal of Organic Chemistry, 2025, 45(4): 1166-1177.
[14]	Zhitong Yang, Hengqian Song, Pan Lei, Jiahang Yan, Weiqing Xie. Efficient Construction of the Core Pentacyclic Skeleton of Communesin Alkaloids [J]. Chinese Journal of Organic Chemistry, 2025, 45(3): 1003-1008.
[15]	Enze Lin, Bijie Li. Recent Progress in Metal-Catalyzed Asymmetric Hydroarylation of Internal Alkenes Through C—H Cleavage [J]. Chinese Journal of Organic Chemistry, 2025, 45(2): 546-558.