Recent Progress in Ruthenium-Catalyzed Asymmetric Functionalization of C(sp²)—H Bonds

doi:10.6023/cjoc202511025

Chinese Journal of Organic Chemistry ›› 2026, Vol. 46 ›› Issue (5): 1795-1812.DOI: 10.6023/cjoc202511025 Previous Articles Next Articles

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钌催化C(sp²)—H键的不对称官能化研究进展

廖云, 唐丽娟, 宗映彤^*(), 于道鸿^*()

赣南师范大学化学与材料学院合成药物化学江西省重点实验室江西赣州 341000

收稿日期:2025-11-27 修回日期:2026-01-12 发布日期:2026-02-11
基金资助:
国家自然科学基金(22461002); 国家自然科学基金(22305046); 江西省自然科学基金(20224BAB213011); 江西省自然科学基金(20232BCJ25050); 江西省自然科学基金(20224BAB213012); 江西省研究生创新专项资金(YC2024-S791); 江西省研究生创新专项资金(YCX23A033); 赣南师范大学大学生创新训练计划(CX240074); 赣南师范大学大学生创新训练计划(CX25051)

Recent Progress in Ruthenium-Catalyzed Asymmetric Functionalization of C(sp²)—H Bonds

Yun Liao, Lijuan Tang, Yingtong Zong^*(), Daohong Yu^*()

Jiangxi Province Key Laboratory of Synthetic Pharmaceutical Chemistry, College of Chemistry and Materials Science, Gannan Normal University, Ganzhou, Jiangxi 341000

Received:2025-11-27 Revised:2026-01-12 Published:2026-02-11
Contact: * E-mail: yudh@gnnu.edu.cn; zongyingtong@gnnu.edu.cn
Supported by:
National Natural Science Foundation of China(22461002); National Natural Science Foundation of China(22305046); Natural Science Foundation of Jiangxi Province(20224BAB213011); Natural Science Foundation of Jiangxi Province(20232BCJ25050); Natural Science Foundation of Jiangxi Province(20224BAB213012); Innovation Special Fund Program of Jiangxi Province for Graduate Students(YC2024-S791); Innovation Special Fund Program of Jiangxi Province for Graduate Students(YCX23A033); Innovation Training Program of Gannan Normal University for College Students(CX240074); Innovation Training Program of Gannan Normal University for College Students(CX25051)

C—H bond activation has emerged as a powerful and sustainable strategy for organic synthesis, as it avoids substrate pre-functionalization and offers simplicity, efficiency, and environmental friendliness. Compared with noble metals such as palladium, rhodium and iridium, ruthenium catalysts are more cost-effective, stable, and readily accessible, thus holding great potential for C—H activation reactions. Ruthenium-catalyzed asymmetric C—H functionalization provides a versatile route to structurally diverse chiral molecules. The progress of asymmetric C(sp²)—H bond functionalization in recent years is dicussed by categorizing asymmetric induction approaches. The reaction scope, functional group tolerance, reaction mechanisms, and limitations of these methods are summarized. The future outlook and existing challenges are also provided.

Key words: ruthenium catalysis, asymmetric catalysis, C—H bond activation, C—H bond functionalization

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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.

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Fig. & Tab. 24

Scheme 1. The first ruthenium-catalyzed asymmetric C—H functionalization

Scheme 2. Transient directing group-assisted asymmetric C—H alkylation reaction for synthesis of indoline derivatives

Scheme 3. Ru catalyzed enatioselective C—H activation of O-linker alkenyl aldehyde toward tetrahydrofurans

Scheme 4. Ru catalyzed enantioselective synthesis 2,3-dihyrobenzofuran and its application

Scheme 5. Versatile chiral amide directed asymmetric C—H functionalization and its application

Scheme 6. Chiral sulfoximine directed ruthenium catalyzed asymmetric C—H functionalization

Scheme 7. Ru catalyzed dual asymmetric C—H activation for synthesis of tetrahydrobenzodifurans

Scheme 8. Ru/chiral acid catalyzed asymmetric C—H functionalization of N-pyridinylindole

Scheme 9. Ru/chiral acid strategy catalyzed C—H hydroarylation for central and axial double enantioinduction

Scheme 10. Chiral acid strategy for construction of sulfur-stereogenic center via asymmetric C—H cyclization

Scheme 11. Ru/chiral acid catalyzed asymmetric [4＋3] annulation of sulfoximines

Scheme 12. Ru/chiral acid catalyzed asymmetric [4＋3] annulation of sulfoximines with sulfoxonium ylide

Scheme 13. Synthesis of chiral benzene ligand and its application in asymmetric C—H functionalization

Scheme 14. Synthesis of chiral arene-Ru catalyst and its application in asymmetric C—H cyclization

Scheme 15. Synthesis of chiral benzene ligand and its application in asymmetric [3＋2] cyclization

Scheme 16. Chiral arene-Ru catalyst catalyzed C—H activation/cyclization via desymmetrization strategy

Scheme 17. Synthesis of chiral indenols catalyzed by chiral arene Ru catalyst

Scheme 18. Modular assembling strategy for synthesis of chiral arene ligand and its application

Scheme 19. One-pot relay catalysis toward formal asymmetric C—H functionalization

Scheme 20. Ru/cinchonine dual catalysis for asymmetric C—H activation and functionalization

Scheme 21. Enantioselective mode of C—H bond activation assisted by chiral induced group

Scheme 22. Two modes of chiral carboxylic-acid-assisted ruthenium catalyzed enantioselective C—H activation

Scheme 23. Enantioselective mechanism of chiral arene ligand-Ru catalyzed asymmetric C—H activation

Scheme 24. Asymmetric C—H functionalization via ruthenium catalysis: a survey of control strategies and reaction types

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钌催化C(sp²)—H键的不对称官能化研究进展

Recent Progress in Ruthenium-Catalyzed Asymmetric Functionalization of C(sp²)—H Bonds

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