氮杂环卡宾钯络合物催化Buchwald-Hartwig胺化反应研究进展

doi:10.6023/A26010032

化学学报 ›› 2026, Vol. 84 ›› Issue (4): 521-571.DOI: 10.6023/A26010032 上一篇下一篇

综述

氮杂环卡宾钯络合物催化Buchwald-Hartwig胺化反应研究进展

徐衍泽^a, 韩南南^a, 刁小琼^a, 袁金伟^a, 肖咏梅^a, 杨亮茹^a^,^*(), 屈凌波^b^,^c

^a 河南工业大学化学化工学院郑州 450000
^b 河南省科学院化学研究所郑州 450002
^c 郑州大学化工学院郑州 450000

投稿日期:2026-01-28 发布日期:2026-03-18
通讯作者: 杨亮茹
作者简介:
徐衍泽, 河南工业大学化学化工学院2023级在读硕士研究生, 主要从事氮杂环卡宾金属化合物的合成及催化性能研究.
韩南南, 河南工业大学化学化工学院2023级在读硕士研究生, 主要从事氮杂环卡宾金属化合物的合成及催化性能研究.
刁小琼, 博士, 河南工业大学化学化工学院讲师, 主要从事有机合成方法学及药物合成等方面的研究.
袁金伟, 博士, 河南工业大学化学化工学院教授, 博士生导师. 主要从事绿色有机合成、有机光催化、药物合成等方面的研究工作.
肖咏梅, 博士, 河南工业大学化学化工学院教授, 硕士生导师. 主要从事天然产物的结构改造及酶催化合成等方面的研究工作.
杨亮茹, 博士, 河南工业大学化学化工学院教授, 博士生导师. 主要研究方向为金属有机化学, 聚焦于氮杂环卡宾金属化合物的合成及性能研究.
屈凌波, 博士, 郑州大学化工学院教授, 河南省科学院化学研究所所长, 博士生导师. 主要研究方向为计算化学、药物化学、药物分子设计和药物分析.
基金资助:
河南省自然科学基金项目(242300420186); 河南省自然科学基金项目(252300421284); 河南省科技攻关项目(262102310429); 河南工业大学拓新团队培育项目(2025TXTD05)

Research Progress on the Buchwald-Hartwig Amination Reactions Catalyzed by N-Heterocyclic Carbene Palladium Complexes

Yanze Xu^a, Nannan Han^a, Xiaoqiong Diao^a, Jinwei Yuan^a, Yongmei Xiao^a, Liangru Yang^a^,^*(), Lingbo Qu^b^,^c

^a School of Chemistry and Chemical Engineering, Henan University of Technology, Zhengzhou 450000, China
^b Institute of Chemistry, Henan Academy of Sciences, Zhengzhou 450002, China
^c School of Chemical Engineering, Zhengzhou University, Zhengzhou 450000, China

Received:2026-01-28 Published:2026-03-18
Contact: Liangru Yang
Supported by:
Natural Science Foundation of Henan Province(242300420186); Natural Science Foundation of Henan Province(252300421284); Key Science and Technology Project of Henan Province(262102310429); Innovative Funds Plan of Henan University of Technology(2025TXTD05)

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摘要/Abstract

碳-氮(C—N)键的高效构建是合成众多含氮生物活性分子的关键步骤. 在多种合成策略中, 钯催化的Buchwald-Hartwig胺化反应(BHA反应)因其条件温和、底物适用范围广, 已成为构建C—N键的重要方法, 其中配体的合理设计对反应性能具有决定性影响. 相较于对空气和水分敏感、稳定性较弱的传统膦配体, 氮杂环卡宾(N-Heterocyclic Carbene, NHC)配体凭借其强σ-给电子能力与弱π-吸电子特性, 所形成的NHC-Pd络合物催化剂表现出优异的稳定性、易于调控的结构以及良好的官能团耐受性, 显著拓展了Buchwald-Hartwig胺化反应的应用范围. 本文系统综述了近十年来NHC-Pd络合物在该反应中的研究进展, 重点围绕原位生成的NHC-Pd(0)型、结构明确的NHC-Pd(II)型以及NHC-Pd(I)型等不同催化剂体系, 阐述其设计理念、催化性能及其在复杂含氮分子合成中的应用实例, 并对该领域未来发展的挑战与前景进行了展望.

关键词: 氮杂环卡宾, 钯催化, Buchwald-Hartwig胺化反应, 配体设计, C—N键构建

Efficient construction of carbon-nitrogen (C—N) bonds is a pivotal step in the synthesis of numerous nitrogen-containing bioactive molecules. Among various synthetic strategies, the palladium-catalyzed Buchwald-Hartwig amination (BHA) reaction has emerged as a crucial method for building C—N bonds due to its mild conditions and broad substrate compatibility. Within this transformation, rational design of ligands plays a decisive role in reaction performance. Compared to traditional phosphine ligands, which are often sensitive to air and moisture and exhibit limited stability, N-heterocyclic carbene (NHC) ligands possess strong σ-donating and weak π-accepting properties. The resulting NHC-Pd catalysts demonstrate excellent stability, tunable structures, and good functional group tolerance, significantly expanding the applicability of the BHA reaction. This review systematically summarizes the research progress of NHC-Pd complexes in this reaction over the past decade, including in situ generated NHC-Pd(0) types, well-defined NHC-Pd(II) types, and NHC-Pd(I) types. The design concepts, catalytic performance, and application examples in the synthesis of complex nitrogen-containing molecules are elaborated. Finally, challenges and future prospects in this field are discussed.

Key words: N-heterocyclic carbine, palladium catalysis, Buchwald-Hartwig amination reaction, ligand design, C—N bond construction

引用此文

徐衍泽, 韩南南, 刁小琼, 袁金伟, 肖咏梅, 杨亮茹, 屈凌波. 氮杂环卡宾钯络合物催化Buchwald-Hartwig胺化反应研究进展[J]. 化学学报, 2026, 84(4): 521-571.

Yanze Xu, Nannan Han, Xiaoqiong Diao, Jinwei Yuan, Yongmei Xiao, Liangru Yang, Lingbo Qu. Research Progress on the Buchwald-Hartwig Amination Reactions Catalyzed by N-Heterocyclic Carbene Palladium Complexes[J]. Acta Chimica Sinica, 2026, 84(4): 521-571.

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图/表 98

图1. C—N交叉偶联反应的代表性应用和Nolan等[48]的开创性工作

Figure 1. Selected applications of C—N cross-coupling reactions and the pioneering progress of Nolan et al.[48]

图式1. Pd/NHC-salt 2催化的BHA反应

Scheme 1. BHA Reaction catalyzed by Pd/NHC-salt 2

图式2. Pd/NHC-salt 3催化的BHA反应

Scheme 2. BHA Reaction catalyzed by Pd/NHC-salt 3

图式3. Pd/NHC-salt 4催化的BHA反应

Scheme 3. BHA Reaction catalyzed by Pd/NHC-salt 4

图式4. Pd/NHC-salt 5催化的BHA反应

Scheme 4. BHA Reaction catalyzed by Pd/NHC-salt 5

图式5. NHC-Pd络合物6催化的BHA反应

Scheme 5. BHA Reaction catalyzed by NHC-Pd complex 6

图式6. NHC-Pd络合物7催化的BHA反应

Scheme 6. BHA Reaction catalyzed by NHC-Pd complexes 7

图式7. NHC-Pd络合物8催化的BHA反应

Scheme 7. BHA Reaction catalyzed by NHC-Pd complexes 8

图式8. NHC-Pd络合物9催化的BHA反应

Scheme 8. BHA Reaction catalyzed by NHC-Pd complexes 9

图式9. NHC-Pd络合物9a催化酰胺BHA反应

Scheme 9. BHA Reaction of amide catalyzed by NHC-Pd complex 9a

图式10. 环扩张型NHC-Pd络合物10催化的BHA反应

Scheme 10. BHA Reaction catalyzed by expanded-ring NHC-Pd complexes 10

图式11. NHC-Pd络合物10a催化的BHA反应

Scheme 11. BHA Reaction catalyzed by NHC-Pd complex 10a

图式12. NHC-Pd络合物11催化的BHA反应

Scheme 12. BHA Reaction catalyzed by NHC-Pd complexes 11

图式13. NHC-Pd络合物12催化的BHA反应

Scheme 13. BHA Reaction catalyzed by NHC-Pd complexes 12

图式14. NHC-Pd络合物13催化的BHA反应

Scheme 14. BHA Reaction catalyzed by NHC-Pd complex 13

图式15. NHC-Pd络合物14催化的BHA反应

Scheme 15. BHA Reaction catalyzed by NHC-Pd complex 14

图式16. NHC-Pd络合物15催化的BHA反应

Scheme 16. BHA Reaction catalyzed by NHC-Pd complexes 15

图式17. NHC-Pd络合物16催化的BHA反应

Scheme 17. BHA Reaction catalyzed by NHC-Pd complexes 16

图式18. NHC-Pd络合物17催化的BHA反应

Scheme 18. BHA Reaction catalyzed by NHC-Pd complexes 17

图式19. NHC-Pd络合物18催化的连续流BHA反应

Scheme 19. Continuous flow BHA reaction catalyzed by NHC-Pd complex 18

图式20. NHC-Pd络合物19催化的BHA反应

Scheme 20. BHA Reaction catalyzed by NHC-Pd complexes 19

图式21. NHC-Pd络合物20催化的BHA反应

Scheme 21. BHA Reaction of aryl chlorides catalyzed by NHC-Pd complex 20

图式22. NHC-Pd络合物21催化的BHA反应

Scheme 22. BHA Reaction catalyzed by NHC-Pd complex 21

图式23. NHC-Pd络合物22和23催化的BHA反应

Scheme 23. BHA Reaction catalyzed by NHC-Pd complexes 22 and 23

图式24. NHC-Pd络合物24催化的BHA反应

Scheme 24. BHA Reaction catalyzed by NHC-Pd complex 24

图式25. NHC-Pd络合物25催化的 BHA 反应

Scheme 25. BHA Reaction catalyzed by NHC-Pd complex 25

图式26. NHC-Pd络合物26催化的BHA反应

Scheme 26. BHA Reaction catalyzed by NHC-Pd complex 26

图式27. NHC-Pd络合物27催化的BHA反应

Scheme 27. BHA Reaction catalyzed by NHC-Pd complex 27

图式28. NHC-Pd络合物28催化的BHA反应

Scheme 28. BHA Reaction catalyzed by NHC-Pd complexes 28

图式29. NHC-Pd络合物29催化的BHA反应

Scheme 29. BHA Reaction catalyzed by NHC-Pd complex 29

图式30. NHC-Pd络合物30催化的BHA反应

Scheme 30. BHA Reaction catalyzed by NHC-Pd complexes 30

图式31. NHC-Pd络合物31催化的BHA反应

Scheme 31. BHA Reaction catalyzed by NHC-Pd complex 31

图式32. Pd-PEPPSI络合物32的合成

Scheme 32. Synthesis of Pd-PEPPSI complexes 32

图式33. NHC-Pd络合物33催化的BHA反应

Scheme 33. BHA Reaction catalyzed by NHC-Pd complexes 33

图式34. NHC-Pd络合物34催化的BHA反应

Scheme 34. BHA Reaction catalyzed by NHC-Pd complexes 34

图式35. NHC-Pd络合物35a催化的BHA反应

Scheme 35. BHA Reaction catalyzed by NHC-Pd complex 35a

图式36. NHC-Pd络合物36催化的BHA反应

Scheme 36. BHA Reaction catalyzed by NHC-Pd complex 36

图式37. NHC-Pd络合物35催化的BHA反应

Scheme 37. BHA Reaction catalyzed by NHC-Pd complexes 35

图式38. NHC-Pd络合物37催化的BHA反应

Scheme 38. BHA Reaction catalyzed by NHC-Pd complexes 37

图式39. NHC-Pd络合物38催化的BHA反应

Scheme 39. BHA Reaction catalyzed by NHC-Pd complexes 38

图式40. NHC-Pd络合物39催化的BHA反应

Scheme 40. BHA Reaction catalyzed by NHC-Pd complex 39

图式41. NHC-Pd络合物40催化的BHA反应

Scheme 41. BHA Reaction catalyzed by NHC-Pd complexes 40

图式42. NHC-Pd络合物41催化的BHA反应

Scheme 42. BHA Reaction catalyzed by NHC-Pd complexes 41

图式43. NHC-Pd络合物42催化的BHA反应

Scheme 43. BHA Reaction catalyzed by NHC-Pd complex 42

图式44. NHC-Pd络合物43催化的BHA反应

Scheme 44. BHA Reaction catalyzed by NHC-Pd complexes 43

图式45. NHC-Pd络合物44催化的BHA反应

Scheme 45. BHA Reaction catalyzed by NHC-Pd complexes 44

图式46. NHC-Pd络合物45催化的BHA反应

Scheme 46. BHA Reaction catalyzed by NHC-Pd complex 45

图式47. NHC-Pd络合物46催化的BHA反应

Scheme 47. BHA Reaction catalyzed by NHC-Pd complex 46

图式48. NHC-Pd络合物47催化的BHA反应

Scheme 48. BHA Reaction catalyzed by NHC-Pd complex 47

图式49. NHC-Pd络合物48催化的BHA反应

Scheme 49. BHA Reaction catalyzed by NHC-Pd complex 48

图式50. NHC-Pd络合物49和50催化的BHA反应

Scheme 50. BHA Reaction catalyzed by NHC-Pd complexes 49 and 50

图式51. NHC-Pd络合物51催化的BHA反应

Scheme 51. BHA Reaction catalyzed by NHC-Pd complexes 51

图式52. NHC-Pd络合物催化机械化学的BHA反应

Scheme 52. BHA Reaction catalyzed by the mechanical of NHC-Pd complexes

图式53. NHC-Pd络合物催化合成PROTAC的BHA反应

Scheme 53. BHA Reaction catalyzed by [Pd-PEPPSI-IHeptCl] for the synthesis of PROTAC

图式54. NHC-Pd络合物在BHA反应中的选择性

Scheme 54. Selectivity in BHA reaction using NHC-Pd complexes

图式55. NHC-Pd络合物52催化BHA反应

Scheme 55. BHA Reaction catalyzed by NHC-Pd complexes 52

图式56. NHC-Pd络合物催化的选择性BHA反应

Scheme 56. Chemoselective BHA reaction catalyzed by NHC-Pd

图式57. NHC-Pd/RuPhos催化的BHA反应

Scheme 57. BHA Reaction catalyzed by NHC-Pd/RuPhos

图式58. NHC-Pd络合物催化BHA反应的研究

Scheme 58. BHA Reaction catalyzed by NHC-Pd complexes

课题组	配体	%Vbur^a	催化底物	反应条件	产率范围
Nolan	IPent	38.2%	未活化氯代芳烃	庚烷, 75 ℃	85%~98%^[77]
Organ	DiMeIHept^Cl	41.5%	位阻胺, 芳基氯	无溶剂, BCF活化	77%~98%^[80]
刘丰收	BIAN-IPent	40.3%	杂芳基氯/胺	空气, CPME	82%~99%^[128]
Szostak	ItOct	44.7%	芳基氯	KO^tBu, 120 ℃	86%^[136]
Szostak	IPr^#	44.7%	芳基氯, 酰胺	LiHDMS, 80 ℃	98%^[147]
Ananikov	IPr*^OMe	36.5%	杂芳基氯/胺	TPEDO, 105 ℃	80%~96%^[137]

表1. 大位阻NHC配体及其Pd络合物的催化性能对比

Table 1. Comparison of catalytic performance of large steric hindrance NHC ligands and NHC-Pd complexes

图式59. NHC-Pd络合物53催化的BHA反应

Scheme 59. BHA Reaction catalyzed by NHC-Pd complexes 53

图式60. NHC-Pd络合物54催化的BHA反应

Scheme 60. BHA Reaction catalyzed by NHC-Pd complex 54

图式61. NHC-Pd络合物55催化的BHA反应

Scheme 61. BHA Reaction catalyzed by NHC-Pd complex 55

图式62. NHC-Pd络合物56催化的BHA反应

Scheme 62. BHA Reaction catalyzed by NHC-Pd complexes 56

图式63. NHC-Pd络合物57催化的BHA反应

Scheme 63. BHA Reaction catalyzed by NHC-Pd complexes 57

图式64. NHC-Pd络合物58催化的BHA反应

Scheme 64. BHA Reaction catalyzed by NHC-Pd complexes 58

图式65. NHC-Pd络合物59催化的BHA反应

Scheme 65. BHA Reaction catalyzed by NHC-Pd complexes 59

图式66. NHC-Pd络合物60催化的BHA反应

Scheme 66. BHA Reaction catalyzed by NHC-Pd complexes 60

图式67. NHC-Pd络合物61催化的BHA反应

Scheme 67. BHA Reaction catalyzed by NHC-Pd complexes 61

图式68. NHC-Pd络合物62催化的BHA反应

Scheme 68. BHA Reaction catalyzed by NHC-Pd complex 62

图式69. NHC-Pd络合物63催化的BHA反应

Scheme 69. BHA Reaction catalyzed by NHC-Pd complex 63

图式70. NHC-Pd络合物64催化的BHA反应

Scheme 70. BHA Reaction catalyzed by NHC-Pd complexes 64

图式71. NHC-Pd络合物65催化的BHA反应

Scheme 71. BHA Reaction catalyzed by NHC-Pd complexes 65

图式72. NHC-Pd络合物66催化的BHA反应

Scheme 72. BHA Reaction catalyzed by NHC-Pd complexes 66

图式73. NCS-钳形NHC-Pd络合物67催化的BHA反应

Scheme 73. BHA Reaction catalyzed by NCS-Pincer NHC-Pd complex 67

图式74. NHC-Pd络合物68催化的BHA反应

Scheme 74. BHA Reaction catalyzed by NHC-Pd complexes 68

图式75. NHC-Pd络合物69催化的BHA反应

Scheme 75. BHA Reaction catalyzed by NHC-Pd complexes 69

图式76. NHC-Pd(I)络合物70催化的BHA反应

Scheme 76. BHA Reaction catalyzed by NHC-Pd(Ⅰ) complex 70

图式77. NHC-Pd络合物催化甲苯磺酸酯BHA反应

Scheme 77. BHA Reaction of tosylates catalyzed by NHC-Pd complex

图式78. NHC-Pd络合物71催化三氟甲磺酸酯BHA反应

Scheme 78. BHA Reaction of triflate catalyzed by NHC-Pd complex 71

图式79. NHC-Pd络合物催化芳基硫醚BHA反应

Scheme 79. BHA Reaction of aryl sulfides catalyzed by NHC-Pd complex

图式80. NHC-Pd络合物催化二芳基亚砜BHA反应

Scheme 80. BHA Reaction of diarylsulfoxides catalyzed by NHC-Pd complexes

图式81. NHC-Pd络合物72催化芳基硫醚BHA反应

Scheme 81. BHA Reaction of aryl sulfides catalyzed by NHC-Pd complex 72

图式82. Pd/NHC鎓盐73体系催化硝基(杂)芳烃BHA反应

Scheme 82. BHA Reaction of nitroarenes catalyzed by Pd/NHC-salt 73

图式83. NHC-Pd络合物11e催化酰胺BHA反应

Scheme 83. BHA Reaction of amide catalyzed by NHC-Pd complex 11e

图式84. NHC-Pd络合物催化酰胺BHA反应

Scheme 84. BHA Reaction of amide catalyzed by NHC-Pd complexes

图式85. NHC-Pd络合物74催化酰胺BHA反应

Scheme 85. BHA Reaction of amide catalyzed by NHC-Pd complex 74

图式86. NHC-Pd络合物49a催化酰胺BHA反应

Scheme 86. BHA Reaction of amide catalyzed by NHC-Pd complex 49a

图式87. NHC-Pd络合物75催化酰胺BHA反应

Scheme 87. BHA Reaction of amide catalyzed by NHC-Pd complex 75

图式88. NHC-Pd络合物32a催化酰胺BHA反应

Scheme 88. BHA Reaction of amide catalyzed by NHC-Pd complex 32a

图式89. NHC-Pd络合物76催化酰胺BHA反应

Scheme 89. BHA Reaction of amide catalyzed by NHC-Pd complex 76

图式90. NHC-Pd络合物在绿色溶剂中催化的酰胺BHA反应

Scheme 90. BHA Reaction of amide catalyzed by NHC-Pd complex in green solvent

图式91. NHC-Pd络合物催化酯类BHA反应

Scheme 91. BHA reaction of esters catalyzed by NHC-Pd complex

图式92. NHC-Pd络合物16c催化酯类BHA反应

Scheme 92. BHA Reaction of esters catalyzed by NHC-Pd complex 16c

图式93. aNHC-Pd络合物77催化的酯类BHA反应

Scheme 93. BHA Reaction of esters catalyzed by aNHC-Pd complexes 77

图式94. NHC-Pd络合物74催化酯类BHA反应

Scheme 94. BHA Reaction of esters catalyzed by NHC-Pd complex 74

图式95. NHC-Pd络合物43c催化酯类BHA反应

Scheme 95. BHA Reaction of esters catalyzed by NHC-Pd complex 43c

图式96. NHC-Pd络合物42催化酯类BHA反应

Scheme 96. BHA Reaction of esters catalyzed by NHC-Pd complex 42

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氮杂环卡宾钯络合物催化Buchwald-Hartwig胺化反应研究进展

Research Progress on the Buchwald-Hartwig Amination Reactions Catalyzed by N-Heterocyclic Carbene Palladium Complexes

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