钳形氮杂环卡宾金属络合物的研究进展

doi:10.6023/cjoc202211006

摘要/Abstract

氮杂环卡宾作为一类结构和性质特殊且便于调控的新型配体, 近年来备受研究者关注. 结构多样、性能各异的多种氮杂环卡宾金属络合物也被广泛合成, 并被应用于催化、合成、材料、医药等领域. 综述了近年来含N、P、S、O、Se等杂原子配位及不同杂化态C的钳形氮杂环卡宾金属络合物的合成及应用研究进展.

关键词: 氮杂环卡宾, 钳形金属络合物, 合成, 应用

As a type of novel ligands featuring special structure and properties that can be easily regulated, N-heterocyclic carbenes (NHCs) have attracted much research attention in recent years. Various NHC metal complexes with typical structure and properties have been synthesized and utilized widely in the fields of catalysis, synthesis, materials, pharmaceuticals, etc. Here, recent research progress on the synthesis and applications of pincer NHC metal complexes containing heteroatoms of N, P, S, O, Se, etc. and C featuring different hybrid state is summarized.

Key words: N-heterocyclic carbene, pincer metal complex, synthesis, application

引用此文

杨亮茹, 郭梦丽, 袁金伟, 王佳美, 夏宇婷, 肖咏梅, 毛璞. 钳形氮杂环卡宾金属络合物的研究进展[J]. 有机化学, 2023, 43(6): 2002-2025.

Liangru Yang, Mengli Guo, Jinwei Yuan, Jiamei Wangx, Yuting Xia, Yongmei Xiao, Pu Mao. Research Progress on Pincer N-Heterocyclic Carbene Metal Complexes[J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2002-2025.

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图/表 59

图式1. 络合物2~6的合成

Scheme 1. Synthesis of complexes 2~6

图式2. 络合物8~9的合成

Scheme 2. Synthesis of complexes 8~9

图式3. 络合物12~16的合成

Scheme 3. Synthesis of complexes 12~16

图式4. 络合物19~21的合成

Scheme 4. Synthesis of complexes 19~21

图式5. 络合物23~24的合成及催化Kumada反应

Scheme 5. Synthesis of complexes 23~24 and catalytic Kumada reaction

图式6. 络合物26的合成及其催化Kumada-Tamao-Corriu偶联反应

Scheme 6. Synthesis of complex 26 and catalytic KumadaTamao-Corriu coupling reaction

图式7. 络合物29~30的合成及其催化Suzuki-Miyaura偶联反应

Scheme 7. Synthesis of complexes 29~30 and catalytic Suzuki- Miyaura coupling reaction

图式8. 络合物32~33的合成及其催化Sonogashira偶联反应

Scheme 8. Synthesis of complexes 32~33 and catalytic Sonogashira coupling reaction

图式9. 络合物35~36的合成

Scheme 9. Synthesis of complexes 35~36

图式10. 络合物38的合成

Scheme 10. Synthesis of complexes 38

图式11. 络合物40~42的合成

Scheme 11. Synthesis of complexes 40~42

图式12. 络合物45~47的合成

Scheme 12. Synthesis of complexes 45~47

图式13. 络合物49~52的合成及其催化胺-醛-乙炔三组分一锅偶联反应

Scheme 13. Synthesis of complexes 49~52 and catalytic amine-aldol-acetylene three-component one-pot coupling reactions

图式14. 络合物53催化苄基铵盐与芳基硼酸的交叉偶联反应

Scheme 14. Cross-coupling reaction of benzylammonium salt with arylboronic acid catalyzed by complex 53

图式15. 络合物54~57的合成

Scheme 15. Synthesis of complexes 54~57

图式16. 络合物61~63的合成

Scheme 16. Synthesis of complexes 61~63

图式17. 络合物65~70的合成

Scheme 17. Synthesis of complexes 65~70

图式18. 络合物72~76, 78~80的合成

Scheme 18. Synthesis of complexes 72~76, 78~80

图式19. 络合物82~83的合成

Scheme 19. Synthesis of complexes 82~83

图式20. 络合物85的合成

Scheme 20. Synthesis of complexes 85

图式21. 络合物87的合成

Scheme 21. Synthesis of complexes 87

图式22. 络合物89~94的合成及其催化酮与异丙醇的氢转移氢化反应

Scheme 22. Synthesis of complexes 89~94 and catalytic hydrogen transfer hydrogenation of ketones with isopropyl alcohol

图式23. 络合物96的合成及催化Suzuki-Miyaura交叉偶联反应

Scheme 23. Synthesis of complex 96 and catalytic Suzuki- Miyaura cross-coupling reaction

图式24. 络合物98~99的合成及催化Suzuki-Miyaura交叉偶联反应

Scheme 24. Synthesis of complexes 98~99 and catalytic Suzuki-Miyaura cross-coupling reaction

图式25. 络合物101~102的合成

Scheme 25. Synthesis of complexes 101~102

图式26. 络合物103的合成及催化酮的加氢反应

Scheme 26. Synthesis of complexes 103 and catalytic hydrogenation of ketones

图式27. 络合物105~106的合成及催化烯烃的加氢反应

Scheme 27. Synthesis of complexes 105~106 and catalytic hydrogenation of olefins

图式28. 络合物108~110的合成及催化环氧乙烷的异构化

Scheme 28. Synthesis of complexes 108~110 and catalytic isomerization of ethylene oxide

图式29. 络合物113~114的合成及催化二氧化碳和氧化环己烯生成环状碳酸酯的反应

Scheme 29. Synthesis of complexes 113~114 and catalytic reactions of CO2 and cyclohexene oxide to form cyclic carbonates

图式30. 络合物117~118的合成

Scheme 30. Synthesis of complexes 117~118

图式31. 络合物120~121的合成及催化不对称aza-Friedel- Crafts反应

Scheme 31. Synthesis of complexes 120~121 and catalytic asymmetric aza-Friedel-Crafts reaction

图式32. 络合物123~124的合成及催化烯烃硅氢化加成反应

Scheme 32. Synthesis of complexes 123~124 and catalytic olefin silica-hydrogenation addition reactions

图式33. 络合物126的合成及催化酯氢化反应

Scheme 33. Synthesis of complex 126 and catalytic ester hydrogenation reaction

图式34. 络合物127~128的合成及催化Sonogashira交叉偶联反应

Scheme 34. Synthesis of complexes 127~128 and catalytic Sonogashira cross-coupling reaction

图式35. 络合物131~132的合成及催化酮的氢转移反应

Scheme 35. Synthesis of complexes 131~132 and catalytic hydrogen transfer reactions of ketones

图式36. 络合物134~137的合成

Scheme 36. Synthesis of complexes 134~137

图式37. 络合物139~140的合成及催化C—N交叉偶联反应

Scheme 37. Synthesis of complexes 139~140 and catalytic C—N cross-coupling reaction

图式38. 络合物142的合成及催化甲酰化反应及N-甲基化反应

Scheme 38. Synthesis of complex 142 and catalytic formylation reaction and N-methylation reaction

图式39. 络合物144~146的合成

Scheme 39. Synthesis of complexes 144~146

图式40. 络合物148和150的合成及催化苯乙酮加氢反应

Scheme 40. Synthesis of complexes 148 and 150 and catalytic acetophenone hydrogenation reaction

图式41. 络合物152~153的合成及催化酮的氢转移氢化反应

Scheme 41. Synthesis of complexes 152~153 and catalytic hydrogen transfer hydrogenation of ketones

图式42. 络合物155的合成及催化羰基还原反应

Scheme 42. Synthesis of complex 155 and catalytic carbonyl reduction reaction

图式43. 络合物157~161的合成

Scheme 43. Synthesis of complexes 157~161

图式44. 络合物163~165的合成

Scheme 44. Synthesis of complexes 163~165

图式45. 络合物166~169的合成及其催化CO2和氧化环己烯的共聚反应

Scheme 45. Synthesis of complexes 166~169 and catalytic copolymerization reaction of CO2 and cyclohexene oxide

图式46. 络合物171~172的合成

Scheme 46. Synthesis of complexes 171~172

图式47. 络合物175~176的合成及其催化咪唑的C—H键直接芳基化反应

Scheme 47. Synthesis of complexes 175~176 and catalytic direct C—H arylation of imidazoles

图式48. 络合物178的合成及催化Mizoroki-Heck和Suzuki-Miyaura偶联反应

Scheme 48. Synthesis of complex 178 and catalytic Mizoroki-Heck and Suzuki-Miyaura coupling reaction

图式49. 络合物181~186的合成

Scheme 49. Synthesis of complexes 181~186

图式50. 络合物188~191的合成

Scheme 50. Synthesis of complexes 188~191

图式51. 络合物192~199的合成和催化醛类的烯丙基化反应

Scheme 51. Synthesis of complexes 192~199 and catalytic the allylation of aldehydes

图式52. 络合物201~205的合成

Scheme 52. Synthesis of complexes 201~205

图式53. 络合物207的合成

Scheme 53. Synthesis of complex 207

图式54. 络合物209~210的合成及催化Suzuki-Miyaura偶联反应和酯类与取代苯胺交叉偶联反应

Scheme 54. Synthesis of complexes 209~210 and catalytic Suzuki-Miyaura coupling reaction and cross-coupling reaction of esters with substituted anilines

图式55. 络合物212~213的合成及催化苯乙烯衍生物的加成反应

Scheme 55. Synthesis of complexes 212~213 and catalytic addition reactions of styrene derivatives

图式56. 络合物215~218的合成

Scheme 56. Synthesis of complexes 215~218

图式57. 络合物220~221的合成

Scheme 57. Synthesis of complexes 220~221

图式58. 络合物224的合成

Scheme 58. Synthesis of complex 224

图式59. 络合物227的合成及其催化酮和伯醇的借氢偶联反应

Scheme 59. Synthesis of complex 227 and catalytic borrowing hydrogen coupling of ketones with primary alcohols

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