光/镍协同催化实现C(sp3)—H键选择性官能团化

doi:10.6023/cjoc202406036

摘要/Abstract

通过C(sp³)—H官能化将易获取的碳氢化合物转化为高附加值化合物引起了学术界和工业界的极大兴趣. 这种转化无疑是一种革命性的方法, 因为它具有固有的原子和步骤经济性, 以及起始材料的丰富性. 经典的过渡金属催化下的C(sp³)—H活化通常需要贵金属催化剂、高温和配位导向基团. 近年来, 光催化领域的快速发展为惰性的C(sp³)—H键活化提供了新的手段. 光诱导的碳氢键断裂和过渡金属镍催化交叉偶联反应的结合已成为C(sp³)—H键选择性功能化的有力工具. 综述了光/镍协同催化下C(sp³)—H键选择性官能团化反应.

关键词: 光/镍协同催化, C(sp³)—H键, 氢原子转移, 交叉偶联反应

The conversion of readily available hydrocarbons into high value-added chiral compounds via C(sp³)—H functionalization has attracted a great deal of interest from both academia and industry. This transformation is undoubtedly a revolutionary approach due to its inherent atom and step economy, as well as the abundance of starting materials. Classical transition- metal-catalyzed C—H activation usually requires noble metal catalysts, high temperatures, and coordinated directing groups. In recent years, the rapid development of the field of photocatalysis has provided new methods for the activation of inert C(sp³)—H bonds. The combination of photoinduced C(sp³)—H bond cleavage and nickel-catalyzed cross-coupling reactions has emerged as a powerful tool for the selective functionalization of C(sp³)—H bonds. Herein, the recent progress in selective C(sp³)—H functionalization via photoredox/nickel dual catalysis is summarized.

Key words: photoredox/nickel dual catalysis, C(sp³)—H bonds, hydrogen atom transfer, cross-coupling reactions

引用此文

王晓琴, 许盛, 平媛媛, 孔望清. 光/镍协同催化实现C(sp³)—H键选择性官能团化[J]. 有机化学, 2025, 45(2): 383-422.

Xiaoqin Wang, Sheng Xu, Yuanyuan Ping, Wangqing Kong. Selective Functionalization of C(sp³)—H Bonds via Photoredox/ Nickel Dual Catalysis[J]. Chinese Journal of Organic Chemistry, 2025, 45(2): 383-422.

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图/表 53

图式1. 传统镍催化偶联反应与光/镍协同催化偶联反应的对比

Scheme 1. Classical Ni-catalyzed vs. Ni-photoredox catalyzed coupling reaction

图式2. 光/镍协同催化下四种反应机制

Scheme 2. Four models of nickel-photoredox catalysis

图式3. 二甲基芳胺C(sp3)—H键的芳基化

Scheme 3. C(sp3)—H arylation of dimethyl anilines

图式4. 芳胺C(sp3)—H键芳基/烯基化

Scheme 4. C(sp3)—H bond arylation/alkenylation of anilines

图式5. 芳胺C(sp3)—H键酰基化

Scheme 5. C(sp3)—H bond acylation of anilines

图式6. 吲哚苄位C(sp3)—H键的芳基化/酰基化

Scheme 6. C(sp3)—H arylation/acylation of indoles

图式7. 1,3-烯炔的1,4-双碳官能团化反应

Scheme 7. 1,4-Dicarbofunctionalization of 1,3-enynes

图式8. 烯丙位C(sp3)—H键芳基化

Scheme 8. Arylation of allylic C(sp3)—H bonds

图式9. 奎宁环作为HAT试剂实现C(sp3)—H键芳基化反应

Scheme 9. Arylation of C(sp3)—H bonds using quinuclidine as HAT reagent

图式10. 从酚类化合物出发实现酰胺的芳基化反应

Scheme 10. Arylation of amide using phenols as aryl sources

图式11. 胺/酰胺作为分子间HAT试剂实现C(sp3)—H键烷基化反应

Scheme 11. Alkylation of C(sp3)—H bonds using amine/sulfamate as HAT reagents

图式12. 苄位C(sp3)—H键的氧官能团化

Scheme 12. Oxy-functionalization of benzylic C(sp3)—H bonds

图式13. 酰胺作为分子内HAT试剂实现C(sp3)—H键官能团化

Scheme 13. C(sp3)—H bonds functionalizations using amide/sulfamate as intramolecular HAT reagent

图式14. 苯甲酰胺氮α位C(sp3)—H的芳基化和烷基化反应

Scheme 14. C(sp3)—H bond arylation and alkylation of amides

图式15. 醛和苄位C(sp3)—H键的交叉脱氢偶联反应

Scheme 15. Cross-dehydrogenative coupling of aldehyde with benzylic C(sp3)—H bonds

图式16. 一级醇参与的脱氢偶联反应

Scheme 16. Dehydrogenative coupling with primary alcohols

图式17. 酰氯和苄位C(sp3)—H键的交叉偶联反应

Scheme 17. Cross coupling of benzylic C(sp3)—H with acyl chlorides

图式18. 异氰酸酯参与下苄位C(sp3)—H键的氨甲酰化反应

Scheme 18. Carbamoylation of benzylic C(sp3)—H bonds with isocyanates

图式19. 光/镍协同催化下立体发散性烯丙基C(sp3)—H键芳基化反应

Scheme 19. Photoredox/nickel dual-catalyzed stereoselective arylation of allylic C(sp3)—H bonds

图式20. 使用过氧化物实现光/镍协同催化下C(sp3)—H键的甲基化

Scheme 20. Photoredox/nickel dual-catalyzed methylation of C(sp3)—H bonds using peroxides

图式21. 硫代磷酰亚胺作为光促HAT试剂实现烯丙基C(sp3)—H键的芳基化

Scheme 21. Arylation of allylic C(sp3)—H bonds using thiophosphoric imide as HAT reagent

图式22. TBADT作为光促HAT试剂实现C(sp3)—H键芳基化

Scheme 22. Arylation of C(sp3)—H bonds using TBADT as photoinduced HAT reagent

图式23. TBADT作为光促HAT试剂实现C(sp3)—H键的酰基化/炔基化

Scheme 23. Acylation/alkynylation of C(sp3)—H bonds using TBADT as photoinduced HAT reagent

图式24. TBADT作为光促HAT试剂实现苄位C(sp3)—H键烯丙基化反应

Scheme 24. Alkylation of allylic C(sp3)—H bonds using TBADT

图式25. TBADT作为光促HAT试剂实现C(sp3)—H键的烷基化

Scheme 25. Alkylation of C(sp3)—H bonds using TBADT as photoinduced HAT reagent

图式26. TBADT作为光促HAT试剂实现C(sp3)—H键甲基化反应

Scheme 26. Methylation of C(sp3)—H bonds using TBADT as photoinduced HAT reagent

图式27. TBADT作为光促HAT试剂实现C(sp3)—H键的胺化/酰胺化

Scheme 27. Amination/amidation of C(sp3)—H bonds using TBADT as photoinduced HAT reagent

图式28. 烯烃的双碳官能团化反应

Scheme 28. Dicarbofunctionalization of olefins

图式29. TBADT参与1,3-烯炔的1,4-双碳官能团化

Scheme 29. 1,4-DCF of 1,3-enynes using TBADT as photoinduced HAT reagent

图式30. 二芳基酮类化合物作为光促HAT试剂的作用机制

Scheme 30. Mechanism of diaryl ketones as photoinduced HAT reagent

图式31. 二芳基酮作为光促HAT试剂实现C(sp3)—H键芳基化/烷基化反应

Scheme 31. Arylation/alkylation of C(sp3)—H bonds using diaryl ketone as photoinduced HAT reagent

图式32. 苄位C(sp3)—H键的碳官能团化反应

Scheme 32. Carbofunctionalization of benzylic C(sp3)—H bonds

图式33. C(sp3)—H键、烯烃及芳基卤化物的三组分偶联反应

Scheme 33. Three-component cross-coupling reaction of C(sp3)—H, alkene and aryl bromide

图式34. 苯甲醛作为光促HAT试剂实现C(sp3)—H键的芳基化/烷基化反应

Scheme 34. Arylation/alkylation of C(sp3)—H bonds using benzaldehyde as photoinduced HAT reagent

X	E⁰(X·/X^—)^a/V	BDE (H—X)/(kJ/mol)
Cl	＋2.03	432
Br	＋1.60	369

表1. X·/X—的氧化还原势能及H—X键的BDE值

Table 1. Redox potential of X·/X— and the BDE of H—X bond

图式35. Molander课题组: α-烷氧基C(sp3)—H键的芳基化反应

Scheme 35. Molander group: arylation of α-alkoxy C(sp3)—H bonds

图式36. 光介导的能量转移过程促进溴自由基的生成以实现C(sp3)—H键的官能团化

Scheme 36. Bromine radical mediate functionalization of C(sp3)—H bonds

图式37. 醚C(sp3)—H键的芳基化反应

Scheme 37. C(sp3)—H arylation of ethers

图式38. 酰胺C(sp3)—H键的芳基化

Scheme 38. C(sp3)—H arylation of amides

图式39. 炔烃的氢烷基化反应

Scheme 39. Hydroalkylation of alkynes

图式40. C(sp3)—H键的酰基化反应

Scheme 40. Acylation of C(sp3)—H bonds

图式41. 其他的C(sp3)—H键酰基化反应实例

Scheme 41. Other C(sp3)—H acylation reactions

图式42. 光/镍协同催化C(sp3)—H键不对称芳基化反应

Scheme 42. Photoredox/nickel dual-catalyzed asymmetric C(sp3)—H arylation

图式43. 光/镍协同催化苄位C(sp3)—H键的不对称芳基化反应

Scheme 43. Photoredox/nickel dual-catalyzed asymmetric arylation of benzylic C(sp3)—H bonds

图式44. 光/镍协同催化苄位C(sp3)—H键的不对称烯基化反应

Scheme 44. Photoredox/nickel dual-catalyzed asymmetric alkenylation of benzylic C(sp3)—H bonds

图式45. 光/镍协同催化α-氨基C(sp3)—H键的不对称芳基化反应

Scheme 45. Photoredox/nickel dual-catalyzed asymmetric arylation of α-amino C(sp3)—H bonds

图式46. 烷基醚C(sp3)—H键的不对称芳基化/烯基化

Scheme 46. Asymmetric arylation/alkenylation of oxacycles C(sp3)—H bonds

图式47. 苯甲酰胺C(sp3)—H键的不对称酰基化反应

Scheme 47. Asymmetric acylation of benzamides C(sp3)—H bonds

图式48. 苄位C(sp3)—H键的不对称酰基化反应

Scheme 48. Asymmetric acylation of benzylic C(sp3)—H bonds

图式49. 饱和氮杂环C(sp3)—H键的不对称酰基化反应

Scheme 49. Asymmetric acylation of saturated N-heterocycles C(sp3)—H bonds

图式50. 使用异氰酸酯实现苄位C(sp3)—H键的不对称氨甲酰化反应

Scheme 50. Asymmetric carbamoylation of benzylic C(sp3)—H bonds with isocyanates

图式51. 酰胺C(sp3)—H键的不对称烷基化反应

Scheme 51. Asymmetric alkylation of amide C(sp3)—H bonds

图式52. C(sp3)—H键、烯烃及芳基溴化物的三组分不对称偶联反应

Scheme 52. Three-component asymmetric coupling of C(sp3)—H, olefin, and Ar-Br

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光/镍协同催化实现C(sp³)—H键选择性官能团化

Selective Functionalization of C(sp³)—H Bonds via Photoredox/ Nickel Dual Catalysis

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