钌催化C(sp²)—H键的不对称官能化研究进展

doi:10.6023/cjoc202511025

有机化学 ›› 2026, Vol. 46 ›› Issue (5): 1795-1812.DOI: 10.6023/cjoc202511025 下一篇

综述与进展

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)

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摘要/Abstract

C—H键活化具有无需预官能团化、简洁、高效和绿色等优点, 已成为有机合成中的一种常用策略. 相比于钯、铑和铱等贵金属, 钌催化剂具有催化剂成本低廉、合成容易及稳定好等优点, 使其在C—H活化方面极具前景, 钌催化的不对称C—H键官能团化研究为结构多样的手性化合物的合成提供了新选择. 以不对称C(sp²)—H官能团化中调控产物手性的策略为分类依据, 综述了近年来在钌催化C(sp²)—H键的不对称官能团化领域的进展, 对反应的适用性、官能团兼容性、反应机理和局限性进行了总结, 对该领域所面临的问题和挑战进行了探讨, 并对未来发展方向进行了展望.

关键词: 钌催化, 不对称催化, C—H键活化, C—H官能团化

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

引用此文

廖云, 唐丽娟, 宗映彤, 于道鸿. 钌催化C(sp²)—H键的不对称官能化研究进展[J]. 有机化学, 2026, 46(5): 1795-1812.

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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图/表 24

图式1. 第一例钌催化的不对称C—H官能团化

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

图式2. 瞬态导向基团辅助的不对称C—H烷基化构建吲哚啉衍生物

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

图式3. 钌催化O-链接烯基醛的不对称C—H活化构建四氢吡喃化合物

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

图式4. 钌催化立体选择性合成2,3-二氢苯并呋喃及其应用

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

图式5. 手性酰胺导向的广谱性不对称C—H官能团化及其应用

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

图式6. 手性亚砜亚胺导向钌催化不对称C—H官能团化反应

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

图式7. 钌催化两次不对称C—H活化构建四氢苯并二呋喃化合物

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

图式8. 钌/手性羧酸催化的N-吡啶吲哚不对称C—H官能团化

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

图式9. 钌/手性羧酸策略催化C—H键氢芳基化实现中心和轴向双手性诱导

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

图式10. 手性羧酸策略实现不对称C—H环化反应构筑硫手性中心

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

图式11. 钌/手性羧酸催化亚砜亚胺的不对称[4＋3]环化反应

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

图式12. 钌/手性羧酸催化硫盐叶立德与亚砜亚胺的[4＋3]环化反应

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

图式13. 手性苯配体的合成及其在不对称C—H键官能团化中的应用

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

图式14. 手性芳基钌催化剂的合成及其在不对称C—H环化反应中的应用

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

图式15. 手性苯配体的合成及其在不对称[3＋2]环化反应中的应用

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

图式16. 手性芳基钌催化剂催化的去对称化C—H键活化/环化反应

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

图式17. 手性芳基钌催化剂催化手性茚醇的合成

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

图式18. 模块化组合策略合成手性苯配体及其应用

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

图式19. 一锅法接力催化实现形式不对称C—H官能团化

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

图式20. 钌/辛可宁协同催化实现不对称C—H活化及官能团化

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

图式21. 手性导向基辅助不对称C—H活化的立体选择性控制

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

图式22. 两种手性羧酸辅助钌催化不对称C—H活化的立体选择性控制模式

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

图式23. 手性苯配体-钌催化的不对称C—H活化的立体选择性机制

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

图式24. 钌催化不对称C—H官能团化的控制策略及催化的反应类型概览

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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