Research Progress on Pincer N-Heterocyclic Carbene Metal Complexes

doi:10.6023/cjoc202211006

Abstract

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

Cite this article

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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Fig. & Tab. 59

Scheme 1. Synthesis of complexes 2~6

Scheme 2. Synthesis of complexes 8~9

Scheme 3. Synthesis of complexes 12~16

Scheme 4. Synthesis of complexes 19~21

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

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

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

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

Scheme 9. Synthesis of complexes 35~36

Scheme 10. Synthesis of complexes 38

Scheme 11. Synthesis of complexes 40~42

Scheme 12. Synthesis of complexes 45~47

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

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

Scheme 15. Synthesis of complexes 54~57

Scheme 16. Synthesis of complexes 61~63

Scheme 17. Synthesis of complexes 65~70

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

Scheme 19. Synthesis of complexes 82~83

Scheme 20. Synthesis of complexes 85

Scheme 21. Synthesis of complexes 87

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

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

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

Scheme 25. Synthesis of complexes 101~102

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

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

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

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

Scheme 30. Synthesis of complexes 117~118

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

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

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

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

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

Scheme 36. Synthesis of complexes 134~137

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

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

Scheme 39. Synthesis of complexes 144~146

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

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

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

Scheme 43. Synthesis of complexes 157~161

Scheme 44. Synthesis of complexes 163~165

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

Scheme 46. Synthesis of complexes 171~172

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

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

Scheme 49. Synthesis of complexes 181~186

Scheme 50. Synthesis of complexes 188~191

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

Scheme 52. Synthesis of complexes 201~205

Scheme 53. Synthesis of complex 207

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

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

Scheme 56. Synthesis of complexes 215~218

Scheme 57. Synthesis of complexes 220~221

Scheme 58. Synthesis of complex 224

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

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钳形氮杂环卡宾金属络合物的研究进展