Recent Advances in the Transformation Reactions of Aromatic Nitriles via C—CN Bond Cleavage

doi:10.6023/cjoc202209007

Abstract

Aromatic nitriles are one of the ubiquitous versatile materials in organic synthesis, and also a class of important synthetic intermediates for a wide range of applications in pharmaceuticals, agricultural chemicals, dyes, spices, and functional materials. However, the C—CN bond of aryl nitriles has rarely been considered as a valuable reaction site due to the high thermodynamic stability. Therefore, the development of simple and efficient methods to catalyze the C—CN bond transformation of aryl nitriles has become one of the hot research topics in recent years. In this review, the recent advances in the transformation reactions of aromatic nitriles via C—CN bond cleavage in the past decade are summarized and classified according to different reaction mechanisms, mainly including transition metal-mediated/catalyzed C—CN transformation, free radical-mediated C—CN transformation, Lewis acid, base or Brønsted acid-mediated C—CN transformation. The reaction substrate compatibility, mechanism, applications, advantages and limitations in this field are also discussed in detail.

Key words: aromatic nitriles, C—CN bond cleavage, transformation reaction, classification of reaction mechanisms

Cite this article

Cunjing Miao, Jiaqi Yao. Recent Advances in the Transformation Reactions of Aromatic Nitriles via C—CN Bond Cleavage[J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1341-1364.

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Fig. & Tab. 41

Figure 1. Classification of aromatic nitriles C—CN bond functionalization reactions

Scheme 1. Ni-catalyzed C—P cross-coupling via C—CN bond cleavage

Scheme 2. Ni-catalyzed arylation of aryl nitriles through the cleavage of C—CN bond

Scheme 3. Ni-catalyzed carbo- and hydro-cyanation of alkynes via C—CN bond activation

Scheme 4. Synthesis of coumarins by Ni-catalyzed cycloaddition via elimination of nitriles

Scheme 5. Synthesis of quinolones by Ni-catalyzed cycloaddition via elimination of nitrile

Scheme 6. Transition metal-catalyzed Mizoroki-Heck reaction using aryl cyanides

Scheme 7. Synthesis of indenes by Ni-catalyzed cycloaddition reaction

Scheme 8. Ni-catalyzed amination of aryl nitriles through the cleavage of C—CN bond

Scheme 9. Ni-catalyzed thiolation of aryl nitriles through the cleavage of C—CN bond

Scheme 10. Rh-catalyzed alkenylation of aryl nitriles via silicon-assisted C—CN bond cleavage

Scheme 11. Rh-catalyzed borylation of nitriles through the cleavage of C—CN bond

Scheme 12. Co-catalyzed carbo- and hydrocyanation of alkynes via C—CN bond activation

Scheme 13. Possible mechanism of photocatalytic cycle

Scheme 14. Photoredox amines C—H arylation reaction with aryl nitriles

Scheme 15. Decarboxylative arylation of α?amino acids via photoredox catalysis

Scheme 16. Direct electron-deficient arylation of N?acyl protected tetrahydroisoquinolines

Scheme 17. Synthesis of sterically hindered primary amines by concurrent tandem photoredox catalysis

Scheme 18. Photoredox catalysis coupling of aldehydes with nitriles to construct aryl substituted alcohols

Scheme 19. Photoredox catalysis coupling of N-(benzyloxy)phthalimides with nitriles to construct aryl substituted alcohols

Scheme 20. Photoredox activation for the direct β-arylation of ketones and aldehydes

Scheme 21. Direct arylation of allylic C(sp3)—H bonds via photoredox catalysis

Scheme 22. Intermolecular, redox-neutral azidoarylation of alkenes via photoredox catalysis

Scheme 23. Photoinduced direct 4-pyridination of C(sp3)—H bonds

Scheme 24. Phenanthrene-catalyzed coupling of carboxylic acids with aromatic nitriles

Scheme 25. BCN-catalyzed coupling of carboxylic acids with aromatic nitriles

Scheme 26. TBA-catalyzed coupling of benzylamines and benzyl alcohols with aromatic nitriles

Scheme 27. Light-induced alkylation of aromatic nitriles in C—C bond metathesis

Scheme 28. Photoredox catalysis coupling of arylidene malonates with aromatic nitriles

Scheme 29. Three-component pyridylation reactions involving aryl ethylene

Scheme 30. Transition-metal-free cross-coupling of aromatic nitriles with amines

Scheme 31. Electroreductive 4?pyridylation of electron-deficient alkenes

Scheme 32. Photoredox catalysis coupling of aldehydes with aromatic nitriles

Scheme 33. Electroreductive pyridylation of quinoxalin-2(1H)? ones

Scheme 34. Cyanide anion as a leaving group in nucleophilic

Scheme 35. Transition-metal-free cross-coupling of cyanides with benzylic zinc reagents

Scheme 36. Arylation of benzyl amines with aromatic nitriles

Scheme 37. Transition-metal-free cross-coupling of aromatic nitriles with C—X bond cleavage

Scheme 38. Lewis acid-catalyzed selective reductive decarboxylative arylation of N?hydroxyphthalimide esters

Scheme 39. Construction of benzo[α]carbazole frameworks

Scheme 40. B2(pin)2-catalyzed perfluoroalkylative pyridylation of alkenes

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基于C—CN键断裂的芳香腈转化反应研究进展