Transition Metal-Catalyzed Reactions of C—H Bonds with Carbon Monoxide

doi:10.6023/cjoc202011008

Abstract

Carbon monoxide is a cheap and reactive gas, and its reactions are atom-economic and can effectively extend the carbon chain. Therefore, CO is an essential carbon source, in particular in the carbonylation reaction. The carbonylation reaction is one of the most effective methods for the synthesis of carbonyl-containing compounds, such as acid anhydrides, amides, esters, etc. On the other hand, carbon-hydrogen bonds widely exist in organic compounds. In recent decades, great progress has been made in the research of activation and functionalization of C—H bonds, and the reactions of C—H bonds with CO also gained considerable interests. The research progress of the reactions of carbon-hydrogen bonds with carbon monoxide catalyzed by transition metals, such as palladium, ruthenium, rhodium, cobalt and copper over the past decades is reviewed.

Key words: transition metal, carbon-hydrogen bonds activation, carbon monoxide, carbonylation

Cite this article

Zechen Wu, Cang Cheng, Yanghui Zhang. Transition Metal-Catalyzed Reactions of C—H Bonds with Carbon Monoxide[J]. Chinese Journal of Organic Chemistry, 2021, 41(6): 2155-2174.

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Fig. & Tab. 105

Scheme 1. Palladium-involved synthesis of aromatic acids from aromatic compounds

Scheme 2. Palladium-catalyzed indole compounds to indole carboxylic acid compounds

Scheme 3. Palladium-catalyzed carboxylation of pyrimidine and thiophene

Scheme 4. Palladium-catalyzed carboxylation of aromatic hydrocarbons

Scheme 5. Mechanism of palladium-catalyzed carboxylation of aromatic hydrocarbons

Scheme 6. Palladium-catalyzed carboxylation of anisole derivatives

Scheme 7. Palladium-catalyzed carboxylation or esterification of furan and thiophene

Scheme 8. Palladium-catalyzed esterification of heteroaromatics

Scheme 9. Mechanism of palladium-catalyzed esterification of indole

Scheme 10. Palladium-catalyzed carbonylation of diaryl ether derivatives

Scheme 11. Palladium-catalyzed synthesis of α-ketoamide from aldehydes

Scheme 12. Mechanism of palladium-catalyzed synthesis of α-ketoamide from aldehydes

Scheme 13. Palladium-catalyzed esterification of 2-phenylpy- ridine

Scheme 14. Palladium-catalyzed esterification of 2-phenoxy- pyridine

Scheme 15. Palladium-catalyzed carbonylation of N-aryl-2- aminopyridine compounds

Scheme 16. Palladium-catalyzed synthesis of amides from L- phenylalanine methyl ester

Scheme 17. Palladium-catalyzed synthesis of benzolactam

Scheme 18. Palladium-catalyzed carbonylation of o-arylanilines

Scheme 19. Palladium-catalyzed synthesis of benzolactam from N-alkyl-ω-arylalkylamine

Scheme 20. Palladium-catalyzed synthesis of benzolactam

Scheme 21. Palladium-catalyzed synthesis of acid anhydride from N-alkylaniline

Scheme 22. Mechanism of palladium-catalyzed synthesis of acid anhydride from N-alkylaniline

Scheme 23. Palladium-catalyzed synthesis of phenanthridinone derivatives

Scheme 24. Palladium-catalyzed carbonylation of N-alkylani- lines

Scheme 25. Palladium-catalyzed oxidative carbonylation of ani- lines

Scheme 26. Palladium-catalyzed carbonylation of N-alkylani- lines

Scheme 27. Palladium-catalyzed synthesis of benzolactam

Scheme 28. Palladium-catalyzed synthesis of isoquinoline derivatives

Scheme 29. Palladium-catalyzed carbonylation of N-arylamide

Scheme 30. Palladium-catalyzed synthesis of phthalimide derivatives

Scheme 31. Palladium-catalyzed ortho-carbonylation of N,N- dimethylbenzylamine

Scheme 32. Palladium-catalyzed carboxylation and amidation of sulfonamides

Scheme 33. Palladium-catalyzed carbonylation of β-arylethyl- amide derivatives

Scheme 34. Palladium-catalyzed carboxylation of o-methyl- benzoic acid

Scheme 35. Palladium-catalyzed carboxylation of anilines

Scheme 36. Palladium-catalyzed synthesis of 1,3-oxazin-6-ones

Scheme 37. Palladium-catalyzed carbonylation of aniline derivatives

Scheme 38. Palladium-catalyzed synthesis of 1-isochromone from phenethyl alcohol

Scheme 39. Palladium-catalyzed synthesis of dibenzopyranone from 2-arylphenol

Scheme 40. Palladium-catalyzed synthesis of benzopyranone from 2-arylphenol

Scheme 41. Palladium-catalyzed synthesis of fused heterocycle

Scheme 42. Palladium-catalyzed carbonylation of alkane

Scheme 43. Palladium-catalyzed oxidative carbonylation of benzyl group

Scheme 44. Palladium-catalyzed synthesis of arylacetamide from benzyl group

Scheme 45. Palladium-catalyzed esterification of 4,4-dimethyl- oxazoline derivatives

Scheme 46. Palladium-catalyzed synthesis of Teleocidin B-4 core

Scheme 47. Palladium-catalyzed carbonylation of β-C(sp 3)—H bond of N-arylamide

Scheme 48. Palladium-catalyzed carbonylation of N-alkylpico- linamides

Scheme 49. Palladium-catalyzed synthesis of pyrrolidone from aliphatic amine

Scheme 50. Palladium-catalyzed synthesis of nitrogen-contai- ning heterocycles from aliphatic amines

Scheme 51. Palladium-catalyzed synthesis of pyrrolidinones from amino alcohol derivatives

Scheme 52. Palladium-catalyzed synthesis of β-lactam from ali- phatic amines

Scheme 53. Mechanism of palladium-catalyzed synthesis of β-lactam from aliphatic amines

Scheme 54. Palladium-catalyzed synthesis of β-lactam

Scheme 55. Palladium-catalyzed synthesis of β-lactams

Scheme 56. Palladium-catalyzed synthesis of γ-lactam from aliphatic amines

Scheme 57. Palladium-catalyzed synthesis of indanone cores

Scheme 58. Mechanism of palladium-catalyzed synthesis of indanone cores

Scheme 59. Palladium-catalyzed amidation and esterification of tert-butylbromobenzene

Scheme 60. Palladium-catalyzed synthesis of β-enoic acid esters

Scheme 61. Palladium-catalyzed carbonylation and esterification of γ-C—H bond

Scheme 62. Ruthenium-catalyzed ortho-acylation of nitrogen-containing aromatic compounds

Scheme 63. Ruthenium-catalyzed carbonylation of phenylpyridine

Scheme 64. Ru/C-catalyzed carbonylation of 2-phenylpyridine

Scheme 65. Ruthenium-catalyzed carbonylation of N-pyridylin- dolines

Scheme 66. Ruthenium-catalyzed carbonylation of 2-phenyl- pyridine with iodobenzene

Scheme 67. Ruthenium-catalyzed carbonylation of 2-phenyl- pyridine with styrene

Scheme 68. Ruthenium-catalyzed acylation of pyridylolefins

Scheme 69. Ruthenium-catalyzed acylation of N-(2-pyridyl)- enamine

Scheme 70. Ruthenium-catalyzed synthesis of indan from aromatic imine

Scheme 71. Ruthenium-catalyzed synthesis of amides from α,β- unsaturated imines

Scheme 72. Ruthenium-catalyzed acylation of imidazole

Scheme 73. Ruthenium-catalyzed acylation of benzimidazoles

Scheme 74. Ruthenium-catalyzed carbonylation of 2-phenyloxazoline

Scheme 75. Ruthenium-catalyzed carbonylation of N-arylpy- razole

Scheme 76. Ruthenium-catalyzed carbonylation with triazole ring as guiding group

Scheme 77. Ruthenium-catalyzed synthesis of phthalimide from aromatic amide

Scheme 78. Ruthenium-catalyzed carbonylation of arylacetamide

Scheme 79. Ruthenium-catalyzed carbonylation of aliphatic amides

Scheme 80. Iridium(I) and rhodium(I)-catalyzed carbonylation of benzene

Scheme 81. Rhodium-catalyzed carbonylation of benzene

Scheme 82. Rhodium-catalyzed carbonylation of azobenzene

Scheme 83. Rhodium-catalyzed carbonylation of N-arylpyrazole

Scheme 84. Rhodium-catalyzed carbonylation of 2-arylpyridine

Scheme 85. Rhodium-catalyzed carbonylation of aromatic compounds

Scheme 86. Rhodium-catalyzed oxidative carbonylation of benzamide

Scheme 87. Rhodium-catalyzed carbonylation of ketimine

Scheme 88. Rhodium-catalyzed synthesis of 6H-isoindolo[2,1- a]indol-6-ones

Scheme 89. Rhodium-catalyzed carbonylation of 2-alkenyl- phenol

Scheme 90. Rhodium-catalyzed carbonylation of indoline

Scheme 91. Rhodium-catalyzed synthesis of aldehydes from propane

Scheme 92. Rhodium-catalyzed synthesis of acetaldehyde from methane

Scheme 93. Rhodium-catalyzed carbonylation of N-(2-pyridyl)- piperazine

Scheme 94. Mechanism of rhodium-catalyzed carbonylation of N-(2-pyridyl)piperazine

Scheme 95. Rhodium-catalyzed carbonylation of N-acylpipe- razine

Scheme 96. Rhodium-catalyzed carbonylation of alkylamine

Scheme 97. Cobalt-catalyzed synthesis of 2-phenylphthalimi- dine from schiff base

Scheme 98. Cobalt-catalyzed carbonylation of aminoquinoline benzamide

Scheme 99. Cobalt-catalyzed esterification of 2-alkenylphenol

Scheme 100. Cobalt-catalyzed electrochemical carbonylation of alkylamine

Scheme 101. Mechanism of cobalt-catalyzed electrochemical carbonylation of alkylamine

Scheme 102. Cobalt-catalyzed carbonylation of benzoyl hydrazide

Scheme 103. Cobalt-catalyzed oxidative carbonylation of aliphatic amides

Scheme 104. Copper-catalyzed carbonylation of alkanes

Scheme 105. Mechanism of copper-catalyzed alkane carbonylation in reaction a of Scheme 104

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过渡金属催化的碳氢键与一氧化碳的反应