Research Progress in Cyanidation of Aromatic Compounds

doi:10.6023/cjoc202602015

Abstract

Aromatic nitrile compounds are not only important components of dyes, industrial and agricultural chemicals, and drug molecules, but also significant intermediates in organic synthesis chemistry. This is due to the fact that the cyano group can be easily converted into other organic functional groups, making the development of new reagents and methods for synthesizing aromatic nitriles of great importance. This paper reviews the major literature on the synthesis of aryl nitriles published from 1884 to 2025, with some from 2026, organized and categorized from the perspective of cyano sources. Initially, chemists used highly toxic NaCN and KCN as cyanide sources; later, methods using potassium ferrocyanide and potassium ferricyanide as non-toxic cyanide sources were developed; in recent years, methods using non-metal cyanides (such as cyanogen iodide) and cyanide-free compounds (such as formamide) as cyanide sources have also emerged. This paper categorizes relevant major literature according to different cyanide sources, and provides the reaction characteristics and scope of application for each cyanide source reagent. Another approach of this review summarizes related literature according to the order of C—H, C—B, C—C, C—N, C—X, C—O, C—S, and C—Si bond transformations into C—CN bonds under the same cyanide source conditions. Notably, this paper also briefly summarizes nearly all 23 references on the latest progress in the synthesis of aromatic nitriles published during 2023~2025. In addition, the review briefly describes the mechanisms of certain reactions.

Key words: arylnitrile, metal cyanide source, non-metallic cyanide source

Cite this article

Mengna Liu, Qiong Wu, Yanhui Shi, Changsheng Cao. Research Progress in Cyanidation of Aromatic Compounds[J]. Chinese Journal of Organic Chemistry, 2026, 46(10): 3838-3864.

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Fig. & Tab. 105

Scheme 1. Pa/Cu-catalyzed cyanation of 2-arylpyridine using CuCN

Scheme 2. Palladium-catalyzed dual ligand-enabled cyanation of arenes

Scheme 3. Copper-catalyzed cyanation of aryldiazonium salts with KCN

Scheme 4. ORT strategy-enabled reduction of nitrate to NO2 for deaminative cyanation of aryl amines

Scheme 5. Copper-catalyzed cyanation of bromobenzene with NaCN

Scheme 6. Palladium-catalyzed cyanation of bromobenzene with NaCN

Scheme 7. Palladium-catalyzed cyanation of aryl sulfonyl chlorides and sodium sulfinates with CuCN

Scheme 8. Cyanation of arenes via iridium-catalyzed borylation

Scheme 9. Decarbonylative cyanation of amides with Zn(CN)2 by palladium catalysis

Scheme 10. Nickel-catalyzed decarbonylative cyanation of esters, amides and acyl cyanides with Zn(CN)2

Scheme 11. Pd/C-catalyzed cyanation of aryl halides with Zn(CN)2

Scheme 12. Palladium-catalyzed cyanation of (hetero)aryl halides, triflates with Zn(CN)2

Scheme 13. Nickel-catalyzed cyanation of (hetero)aryl chlorides with Zn(CN)2

Scheme 14. Ni-catalyzed cyanation of aryl and heteroaryl chlorides

Scheme 15. Nickel-catalyzed cyanation of (hetero)aryl halides using high-throughput experimental techniques

Scheme 16. Nickel-catalyzed selective C—H cyanation via aromatic thianthrenium salts

Scheme 17. Palladium-catalyzed cyanation of diaryl sulfoxides with Zn(CN)2

Scheme 18. Palladium-catalyzed cyanation of indoles with K4-[Fe(CN)6]

Scheme 19. Palladium-catalyzed cyanation of aryl carboxylic acids with K4[Fe(CN)6]

Scheme 20. Copper-mediated cyanation of aldehydes with K3[Fe(CN)6]

Scheme 21. Plausible mechanism for the copper-mediated cyanation of aldehydes with K3[Fe(CN)6]

Scheme 22. Copper-catalyzed cyanation of benzyl alcohols with K4[Fe(CN)6]

Scheme 23. Plausible mechanism of copper-catalyzed cyanation of benzyl alcohols with K4[Fe(CN)6]

Scheme 24. Palladium-catalyzed cyanation of (hetero)aryl halides with K4[Fe(CN)6]

Scheme 25. Ni-catalyzed cyanation of (hetero)aryl electrophiles using [K4[Fe(CN)6]

Scheme 26. Nanoparticles of Ni-γAl2O3 catalyzed the cyanation of haloaromatics by using [K4[Fe(CN)6]

Scheme 27. Palladium-catalyzed cyanation of aryl mesylates with K4[Fe(CN)6]

Scheme 28. Palladium-catalyzed cyanation of aryl sulfonium salts with K4[Fe(CN)6]

Scheme 29. Copper-catalyzed cyanation of arylboronic reagents with cyanogen iodide

Scheme 30. Plausible mechanism of copper-catalyzed cyanation of aryl-and alkenylboronic reagents with cyanogen iodide

Scheme 31. Nickel-catalyzed reductive cyanation of aryl halides with cyanogen bromide

Scheme 32. Non-metal-catalyzed cyanation of 4-methoxyben-zenediazonium o-benzenedisulfonimide with tetrabutylammonium cyanide

Scheme 33. Palladium-catalyzed cyanation of aryl halides and borons with CuSCN

Scheme 34. Visible-light-induced controlled C—H cyanation of indolizines

Scheme 35. Electrophilic aryl C(sp2)—H cyanation with sodium cyanate by PIII/PV=O-catalyzed phase transfer activation

Scheme 36. Copper-catalyzed cyanation of arenes with CH3CN

Scheme 37. Copper-catalyzed cyanation of indoles using acetonitrile

Scheme 38. Palladium-catalyzed cyanation of indoles using acetonitrile

Scheme 39. Palladium-catalyzed cyanation of arenediazonium tetrafluoroborate using acetonitrile

Scheme 40. Ni-catalyzed cyanation of (hetero)aryl halides with acetonitrile as cyano source

Scheme 41. Nickel-catalyzed cyanation of aryl chlorides and triflates using butyronitrile

Scheme 42. Possible mechanism of nickel-catalyzed cyanation of aryl chlorides and triflates using butyronitrile

Scheme 43. Gold-catalyzed cyanation of iodoarene with acetone cyanohydrin

Scheme 44. Photoinduced nickel-catalyzed cyanation of aryl bromide

Scheme 45. Palladium-catalyzed cyanation of aryl halide with benzyl cyanide

Scheme 46. Palladium-catalyzed cyanation of aryl halide with benzyl cyanide

Scheme 47. Copper-mediated cyanation of aryl boronic acids using benzyl cyanide

Scheme 48. Palladium-catalyzed cyanation of arenediazonium tetrafluoroborate with 2-(piperidin-1-yl)acetonitrile

Scheme 49. Nickel-catalyzed cyanation of phenol derivatives with aminoacetonitriles

Scheme 50. Plausible mechanism of the cyanation of phenol derivatives with aminoacetonitriles

Scheme 51. Palladium-catalyzed denitrative synthesis of aryl nitriles from nitroarenes and morpholinoacetonitrile

Scheme 52. Palladium-catalyzed cyanation of aryl halides with α-cyanoacetates

Scheme 53. Copper-mediated cyanation of aryl halides with α-cyanoacetates

Scheme 54. Direct and site-selective C—H cyanation of (hetero)arenes by a nontoxic cyano source

Scheme 55. Cyanation of arenes with TMSCN via organic photoredox catalysis

Scheme 56. Copper-mediated cyanation of arylboronic acids with TMSCN

Scheme 57. Nickel-catalyzed decarbonylative cyanation of acyl chlorides with TMSCN

Scheme 58. Palladium-catalyzed cyanation of aryl halides using TMSCN

Scheme 59. Cyanation of aryl grignard reagents and lithium reagents with DMMN without metal catalysis

Scheme 60. Nickel-catalyzed cyanation of aryl amides with 4-cyanopyridine

Scheme 61. Nickel-catalyzed and photochemically enabled cyanation of aryl halides with 1,4-DCB

Scheme 62. Plausible mechanism of nickel-catalyzed and photochemically enabled cyanation of aryl halides with 1,4-DCB

Scheme 63. Nickel-catalyzed cyanation of aryl halides with 4-cyanopyridine N-oxide

Scheme 64. Light-triggered, Ni-catalyzed cyanation of aryl triflates with 1,4-dicyanobenzene as the CN source

Scheme 65. Reversible functional group metathesis between aryl nitriles and aryl thioethers

Scheme 66. Plausible mechanism of reversible functional group metathesis between aryl nitriles and aryl thioethers

Scheme 67. Rhodium-catalyzed cyanation of arenes with directing groups using NCTS

Scheme 68. Lewis acid-mediated cyanation of β-naphthol derivatives using NCTS

Scheme 69. Rh(III)-catalyzed atroposelective C—H cyanation of 1-aryl benzo[h]isoquinolines

Scheme 70. Rhodium-catalyzed cyanation of aryl boronic acids with NCTS

Scheme 71. Cyanidation of (hetero)aryl bromides with NCTS without metal catalysis

Scheme 72. Palladium-catalyzed cyanation of arenediazonium tetrafluoroborates and aryl halides with NCTS

Scheme 73. Cobalt-catalyzed C—H cyanation of (hetero)arenes with NNS

Scheme 74. Plausible mechanism of cobalt-catalyzed C—H cyanation of (hetero)arenes

Scheme 75. Ni-catalyzed C—H cyanation of (hetero)arenes with NCITD as a cyanation reagent

Scheme 76. Palladium-catalyzed cyanation of aryl(pseudo)ha-lides using a redox-active BICD

Scheme 77. Catalytic cyanation of aryl halides with electrophilic N-CN reagent (BICD)

Scheme 78. Cyanation of aryl trimethylammonium salts and tosyl cyanide via electrochemical cleavage of C—N bonds

Scheme 79. Cyanation of arylboronic acids with trityl isocyanide

Scheme 80. Palladium-catalyzed cyanation of aryl iodides with hexamethylenetetramine

Scheme 81. Plausible mechanism of palladium-catalyzed cyanation of aryl iodides with HMTA

Scheme 82. Copper-catalyzed cyanation of aryl iodides with nitromethane

Scheme 83. Plausible mechanism of copper-catalyzed cyanation of aryl iodides with nitromethane

Scheme 84. Palladium-catalyzed cyanation of aryl halides with formamide

Scheme 85. Copper-catalyzed cyanation of aryl halides with formamide

Scheme 86. Nickel-catalyzed cyanation of (hetero)aryl halides with formamide

Scheme 87. Zinc-catalyzed cyanation of aryl halides with formamide

Scheme 88. Electrochemical cyanation of electron-rich aromatic rings by using 5-aminotetrazole

Scheme 89. Pd catalyzed copper-mediated cyanation of arenes with DMF and NH4I

Scheme 90. Copper-mediated cyanation of heteroarene with DMF and NH4I

Scheme 91. Palladium-catalyzed cyanation of 3-position of indole with DMSO and NH4HCO3

Scheme 92. Copper-mediated cyanation of arylboron compounds and arenes with DMF and NH4I

Scheme 93. Copper-catalyzed cyanation of aryl iodides with DMF and NH4HCO3

Scheme 94. Plausible mechanism of the copper-catalyzed cyanation of aryl iodides with DMF and NH4HCO3

Scheme 95. Palladium-catalyzed cyanation of aryl halides with DMF and CAN

Scheme 96. Copper-catalyzed cyanation of aryl iodide with DMSO and urea

Scheme 97. Copper-catalyzed cyanation of aryl halides with CO2 and NH3

Scheme 98. Plausible mechanism of copper-catalyzed cyanation of aryl iodides with CO2 and NH3

Scheme 99. Nickel-catalyzed cyanation of aryl chlorides with CO2 and NH3

Table 1. Catalytic cyanation with other related cyanating reagents

Scheme 100. Plausible mechanism of nickel-catalyzed cyanation of aryl chlorides with CO2 and NH3

Scheme 101. Palladium-catalyzed cyanation of aryl halides with ClCF2H and NaNH2

Scheme 102. Copper-mediated cyanation of aryl halides with Ph3P＋CF2${\text{CO}}_{2}^{-}$ and NaNH2

Scheme 103. Nickel-catalyzed cyanation of aryl thioether using CO2 and NH3

Scheme 104. Copper-mediated cyanation of organosilanes with DMF and NH4I

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