Recent Advances in Copper-Catalyzed C(sp3)—H Bond Functionalization of N-Fluorosulfonamides via Hydrogen Atom Transfer

doi:10.6023/cjoc202602023

Chinese Journal of Organic Chemistry ›› 2026, Vol. 46 ›› Issue (7): 2529-2543.DOI: 10.6023/cjoc202602023 Previous Articles Next Articles

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基于氢原子转移策略的铜催化N-氟代磺酰胺C(sp³)—H键官能团化研究进展

张文钰^a, 刘星雨^a, 薛琦^a, 李杨^a^,^*(), 汪苇杭^b^,^*(), 李金恒^a^,^c^,^*()

^a 青岛科技大学化工学院山东青岛 266042
^b 中南大学湘雅二医院感染科湖南省病毒性肝炎临床医学研究中心长沙 410011
^c 河南师范大学化学化工学院河南新乡 453007

收稿日期:2026-02-28 修回日期:2026-05-01 发布日期:2026-06-03
基金资助:
国家自然科学基金(22001108); 国家自然科学基金(22271245); 江西省科技计划(20243BCE51084); 江西省科技计划(20242BAB25126); 山东省泰山学者建设(tsqn202408199); 及河南师范大学化学与化学工程学院开放研究基金(2021ZD01)

Recent Advances in Copper-Catalyzed C(sp³)—H Bond Functionalization of N-Fluorosulfonamides via Hydrogen Atom Transfer

Wenyu Zhang^a, Xingyu Liu^a, Qi Xue^a, Yang Li^a^,^*(), Weihang Wang^b^,^*(), Jinheng Li^a^,^c^,^*()

^a College of Chemical Engineering, Qingdao University of Science and Technology, Qingdao, Shandong 266042
^b Clinical Research Center for Viral Hepatitis in Hunan Province, Department of Infectious Diseases, The Second Xiangya Hospital of Central South University, Changsha 410011
^c School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007

Received:2026-02-28 Revised:2026-05-01 Published:2026-06-03
Contact: *E-mail: liyang1989@hnu.edu.cn;218202047@csu.edu.cn;jhli@hnu.edu.cn
Supported by:
National Natural Science Foundation of China(22001108); National Natural Science Foundation of China(22271245); Science and Technology Project of Jiangxi Province(20243BCE51084); Science and Technology Project of Jiangxi Province(20242BAB25126); Taishan Scholars Construction Projects of Shandong Province(tsqn202408199); Open Research Fund of School of Chemistry and Chemical Engineering, Henan Normal University(2021ZD01)

The selective functionalization of C—H bonds is one of the core research areas in modern synthetic chemistry. Among these, C(sp³)—H bonds are characterized by high bond dissociation energy and weak acidity, and they are widely present in diverse molecular structures with highly similar chemical environments. Therefore, achieving precise control over their site selectivity remains a significant challenge. The hydrogen atom transfer strategy offers new possibilities for the direct transformation of unactivated C(sp³)—H bonds. In recent years, copper-catalyzed C(sp³)—H bond functionalization reactions using N-fluorinated sulfonamides based on the hydrogen atom transfer strategy have developed rapidly. The research progress in this field is reviewed with focus on reaction mechanisms and substrate scope, and an outlook on future development direc- tions and application prospects is provided.

Key words: hydrogen atom transfer, copper catalysis, N-fluorosulfonamide, C—H bond

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Wenyu Zhang, Xingyu Liu, Qi Xue, Yang Li, Weihang Wang, Jinheng Li. Recent Advances in Copper-Catalyzed C(sp³)—H Bond Functionalization of N-Fluorosulfonamides via Hydrogen Atom Transfer[J]. Chinese Journal of Organic Chemistry, 2026, 46(7): 2529-2543.

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Fig. & Tab. 18

Scheme 1. Copper-catalyzed arylation of N-fluorosulfonamides

Scheme 2. Copper-catalyzed reaction of N-fluorosulfonamides with alkenes

Scheme 3. Copper-catalyzed reaction of N-fluorosulfonamides

Scheme 4. Copper-catalyzed reaction of N-fluorosulfonamides with heteroaromatic hydrocarbons

Scheme 5. Copper-catalyzed cyanation of N-fluorosulfonamides

Scheme 6. Copper-catalyzed reaction of N-fluorosulfonamides

Scheme 7. Copper-catalyzed reaction of N-fluorosulfonamides with alkynes

Scheme 8. Copper-catalyzed trifluoromethylation of N-fluorosulfonamides

Scheme 9. Copper-catalyzed single-component reaction of N-fluorosulfonamides

Scheme 10. Copper-catalyzed azidation of N-fluorosulfonamides

Scheme 11. Copper-catalyzed reaction of N-fluorosulfonamides with TMSNCO

Scheme 12. Copper-catalyzed S/Se-trifluoromethylation of N-fluorosulfonamide

Scheme 13. Copper-catalyzed sulfenylation of N-fluorosulfonamides

Scheme 14. Copper-catalyzed selenylation of N-fluorosulfonamides

Scheme 15. Copper-catalyzed sulfonylation of N-fluorosulfonamides

Scheme 16. Copper-catalyzed sulfidation of N-fluorosulfonamides

Scheme 17. Copper-catalyzed sulfidation of N-fluorosulfonamides

Scheme 18. Copper-catalyzed carbonylation of N-fluorosulfonamides

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基于氢原子转移策略的铜催化N-氟代磺酰胺C(sp³)—H键官能团化研究进展

Recent Advances in Copper-Catalyzed C(sp³)—H Bond Functionalization of N-Fluorosulfonamides via Hydrogen Atom Transfer

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基于氢原子转移策略的铜催化N-氟代磺酰胺C(sp3)—H键官能团化研究进展