光/镍协同催化C(sp2)—C(sp3)键构建研究进展

doi:10.6023/cjoc202504001

摘要/Abstract

光/过渡金属协同催化体系已成为现代有机合成的重要研究方向. 近年来, 以地球丰产金属镍为催化中心、结合光催化的协同催化体系取得了突破性进展. 通过光化学过程, 该体系可高效转化多种烷基自由基前体, 反应条件温和, 在选择性构建C(sp²)—C(sp³)键方面展现出了显著优势. 光催化产生烷基自由基物种与镍催化C(sp²)—C(sp³)键构建的协同作用机制, 不仅拓展了交叉偶联反应的底物适用范围, 还为将大宗化学品转化为高附加值精细化学品开辟了新途径. 本综述梳理了该领域的研究进展, 重点关注烷基自由基前体的多样性来源, 并简要阐释了相关催化机理.

关键词: 光催化, 镍催化, 协同催化, 烷基自由基, C(sp²)—C(sp³)键

The photoredox/transition metal dual catalysis system has emerged as a pivotal research direction in modern organic synthesis. Recent breakthroughs have been achieved in dual catalytic systems centered on earth-abundant nickel and integrated with photoredox catalysis. This system efficiently converts diverse alkyl radicals precursors through photochemical processes under mild reaction conditions and demonstrates remarkable advantages in the selective construction of C(sp²)—C(sp³) bonds. Notably, the synergistic mechanism between photocatalytic generation of alkyl radical species and nickel-catalyzed C(sp²)—C(sp³) cross-coupling not only expands the substrate scope of cross-coupling reactions, but also unlocks novel pathways for the conversion of bulk chemicals into high-value-added fine chemicals. This review summarizes the research progress in this field, highlighting the diverse sources of alkyl radical precursors and discussing key catalytic mechanisms.

Key words: photoredox catalysis, nickel catalysis, dual catalysis, alkyl radical, C(sp²)—C(sp³) bonds

引用此文

高根伟, 李震, 李炎, 陆熹. 光/镍协同催化C(sp²)—C(sp³)键构建研究进展[J]. 有机化学, 2025, 45(6): 1905-1919.

Genwei Gao, Zhen Li, Yan Li, Xi Lu. Recent Progress on the Construction of C(sp²)—C(sp³) Bonds via Photoredox/Nickel Dual Catalysis[J]. Chinese Journal of Organic Chemistry, 2025, 45(6): 1905-1919.

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图/表 29

图式1. 不同烷基自由基生成机制参与的光/镍协同催化反应

Scheme 1. Photoredox/nickel dual catalytic reactions involving different alkyl radical generation mechanisms

图式2. 光/镍协同催化烷基羧酸与芳基卤化物交叉偶联反应

Scheme 2. Dual catalysis of photoredox/nickel for the coupling reaction of alkyl carboxylic acids with aryl halides

图式3. α-氨基酸的对映选择性脱羧芳基化反应

Scheme 3. Enantioselective decarboxylative arylation of α-amino acids

图式4. 铁/镍金属光氧化还原催化的脱羧交叉偶联反应

Scheme 4. Decarboxylative cross-coupling enabled by Fe and Ni metallaphotoredox catalysis

图式5. 金属光氧化还原醇脱氧芳基化

Scheme 5. Metallaphotoredox-enabled deoxygenative arylation of alcohols

图式6. 光/镍协同催化有机硼试剂的交叉偶联反应

Scheme 6. Cross-coupling of organoboron enabled by photoredox/nickel dual catalysis

图式7. 可见光催化双儿茶酚硅化合物交叉偶联反应

Scheme 7. Visible-light photocatalytic cross-coupling of bis-catecholato silicon compounds

图式8. 光/镍协同催化烯基卤化物与烷基硅酸盐交叉偶联反应

Scheme 8. Cross-coupling reaction of alkenyl halides with alkylsilicates via photoredox/nickel dual catalysis

图式9. 光/镍协同催化烯烃对映选择性三组分碳芳基化反应

Scheme 9. Enantioselective three-component carboarylation of alkenes enabled by photoredox/nickel dual catalysis

图式10. 光/镍协同催化芳基卤化物与4-烷基-1,4-二氢吡啶的交叉偶联反应

Scheme 10. Cross-coupling reaction of aryl halides with 4-alk-yl-1,4-dihydropyridines via photoredox/nickel dual catalysis

图式11. 芳基溴化物与醛衍生的1,4-二氢吡啶的交叉偶联反应

Scheme 11. Cross-coupling of 1,4-dihydropyridine derived from aldehyde with aryl bromides

图式12. 单电子还原产生烷基自由基参与的光/镍协同催化体系

Scheme 12. Photoredox/nickel dual catalysis containing single electron reduction to generate alkyl radicals

图式13. NEt3驱动光/镍协同催化芳基溴化物与烷基溴化物的亲电交叉偶联反应

Scheme 13. NEt3 driven photoredox/nickel dual catalysis for cross-electrophile coupling of aryl bromide and alkyl bromide

图式14. 光/镍协同催化芳基卤化物与二氯甲烷的还原交叉偶联

Scheme 14. Reductive cross-coupling of aryl halides with dichloromethane via photoredox/nickel dual catalysis

图式15. 光/镍协同催化的还原交叉偶联反应制备手性α-芳基磷酸酯

Scheme 15. Access to chiral α-aryl phosphates via dual nickel-and photoredox-catalyzed reductive cross-coupling

图式16. 可见光诱导镍催化糖基氯和芳基溴还原交叉偶联制备C-芳基糖苷

Scheme 16. Preparation of C-aryl glycosides via visible-light induced nickel-catalyzed reductive cross-coupling of glycosyl chlorides and aryl bromides

图式17. 醇为还原剂的金属光氧化还原催化对映选择性交叉亲电偶联

Scheme 17. Metallaphotoredox-catalyzed enantioselective cross-electrophile coupling using alcohols as reducing agents

图式18. 硅基自由基活化的金属光氧化还原催化的亲电交叉偶联反应

Scheme 18. Cross-electrophile coupling of metal photocatalytic oxidation-reduction activated by silicon-based radicals

图式19. 非活性烷基氯化物的亲电交叉偶联反应

Scheme 19. Cross-electrophile coupling of unactivated alkyl chlorides

图式20. 光/镍协同催化二甲基苯胺与芳基卤化物交叉偶联生成α-芳基苯胺

Scheme 20. Cross-coupling of dimethylaniline with aryl halides to generate α-arylaniline via photoredox/nickel dual catalysis

图式21. 光/镍协同催化芳基卤化物与胺的C(sp3)—H官能化反应

Scheme 21. C(sp3)—H functionalization of amines with aryl halides by photoredox/nickel dual catalysis

图式22. 光/镍协同催化C(sp3)—H键直接酰基化反应

Scheme 22. Direct acylation of C(sp3)—H bonds enabled by nickel/photoredox dual catalysis

图式23. 脂肪族强C(sp3)—H键的直接芳基化

Scheme 23. Direct arylation of strong aliphatic C(sp3)—H bonds

图式24. C-糖苷的立体选择性和位点发散性合成

Scheme 24. Stereoselective and site-divergent synthesis of C-glycosides

图式25. C(sp3)—H键的三重催化烷基化交叉偶联

Scheme 25. Triple catalytic alkylative cross-coupling of C(sp3)—H bonds

图式26. 催化生成卤素自由基实现C(sp3)—H键直接交叉偶联反应

Scheme 26. Direct C(sp3)—H cross coupling enabled by catalytic generation of halogen radicals

图式27. 镍催化光化学卤素原子介导的C(sp3)—H芳基化反应机理研究

Scheme 27. Mechanism investigation of nickel-catalyzed photochemical halogen atom-mediated C(sp3)—H arylation

图式28. C(sp3)—H键直接对映选择性酰基化合成α-氨基酮

Scheme 28. Direct enantioselective C(sp3)—H acylation for the synthesis of α-amino ketones

图式29. 三重激发态酮与镍催化剂协同催化的C(sp3)—H键芳基化反应

Scheme 29. C(sp3)—H arylation enabled by the synergy of triplet excited ketones and nickel catalysts

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光/镍协同催化C(sp²)—C(sp³)键构建研究进展

Recent Progress on the Construction of C(sp²)—C(sp³) Bonds via Photoredox/Nickel Dual Catalysis

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