基于C—CN键断裂的芳香腈转化反应研究进展

doi:10.6023/cjoc202209007

摘要/Abstract

芳香腈是有机合成中普遍存在的原料之一, 也是一类重要的合成中间体, 可广泛应用于药物、农用化学品、染料、香料以及功能材料等领域, 但由于C—CN键热力学稳定性较高, 很少被认为是一个有价值的反应位点. 因此, 开发简便、高效的方法催化芳香腈C—CN键转化成为近年研究热点之一. 综述了近十年来基于C—CN键断裂的芳香腈转化反应研究进展, 并按照不同反应原理分类, 主要包括过渡金属介导/催化的C—CN的转化、自由基介导的C—CN的转化、Lewis酸、碱或Brønsted酸介导的C—CN的转化, 详细讨论了反应底物普适性、反应机理和应用, 并对该领域的发展前景和局限性进行了总结.

关键词: 芳香腈, C—CN键断裂, 转化反应, 反应原理分类

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

引用此文

缪存静, 姚佳琪. 基于C—CN键断裂的芳香腈转化反应研究进展[J]. 有机化学, 2023, 43(4): 1341-1364.

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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图/表 41

图1. 芳香腈C—CN键官能团化反应分类

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

图式1. 镍催化C—CN键断裂的C—P键交叉偶联反应

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

图式2. 镍催化C—CN键断裂的芳腈类化合物芳基化反应

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

图式3. 镍催化C—CN键活化的炔烃碳化和氢氰化反应

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

图式4. 通过镍催化环加成消除腈合成香豆素类

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

图式5. 通过镍催化环加成消除腈合成喹诺酮类物质

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

图式6. 过渡金属催化芳基氰化物的Mizoroki-Heck反应

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

图式7. 通过镍催化环加成反应合成茚类物质

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

图式8. 镍催化C—CN键断裂的芳腈类化合物胺化反应

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

图式9. 镍催化C—CN键断裂的芳腈类化合物硫化反应

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

图式10. 硅辅助的铑催化芳腈C—CN键断裂烯基化反应

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

图式11. 铑催化C—CN键断裂实现腈类化合物的硼化反应

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

图式12. 钴催化C—CN键活化的炔烃碳化和氢氰化反应

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

图式13. 光催化循环的可能机理

Scheme 13. Possible mechanism of photocatalytic cycle

图式14. 光氧化芳腈和胺的C—H芳基化反应

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

图式15. 通过光催化实现α-氨基酸的脱羧芳烃化

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

图式16. N-酰基保护的四氢异喹啉缺电子芳基化反应

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

图式17. 光催化串联合成空间位阻伯胺

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

图式18. 可见光催化醛与芳香腈偶联构建芳基取代醇

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

图式19. 可见光催化N-(苄氧基)邻苯二甲酰亚胺与芳香腈偶联构建芳基取代醇

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

图式20. 光催化活化酮和醛的直接β-芳基化

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

图式21. 光氧化催化烯丙基C(sp3)—H键的直接芳基化

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

图式22. 光催化烯烃分子间、氧化还原中性的叠氮芳基化

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

图式 23. 光诱导的C(sp3)—H键直接4-吡啶化反应

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

图式24. 菲催化羧酸与芳香腈的偶联反应

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

图式25. 硼碳氮化物催化羧酸与芳香腈的偶联反应

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

图式26. TBA催化苄胺、苄醇与芳香腈的偶联反应

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

图式27. 光诱导芳香腈C—C键复分解烷基化反应

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

图式28. 光催化的亚芳基丙二酸盐和氰基芳烃偶联的反应

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

图式29. 芳基乙烯参与的三组分吡啶化反应

Scheme 29. Three-component pyridylation reactions involving aryl ethylene

图式30. 芳香腈与胺的无过渡金属交叉偶联

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

图式31. 缺电子烯烃的电还原4-吡啶基化

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

图式32. 可见光催化醛与芳香腈的偶联反应

Scheme 32. Photoredox catalysis coupling of aldehydes with aromatic nitriles

图式33. 喹啉-2(1H)酮的电还原吡啶基化

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

图式34. 氰基作为离去基团发生的芳基亲核取代反应

Scheme 34. Cyanide anion as a leaving group in nucleophilic

图式35. 氰化物与苄基锌试剂的无过渡金属交叉偶合

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

图式36. 苄胺与芳香腈的芳基化反应

Scheme 36. Arylation of benzyl amines with aromatic nitriles

图式37. 芳香腈与C—X键断裂的无过渡金属交叉偶联

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

图式38. Lweis酸催化N-羟基邻苯二甲酰亚胺酯的选择性还原脱羧芳基化

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

图式39. 苯并[α]咔唑化合物的构建

Scheme 39. Construction of benzo[α]carbazole frameworks

图式40. 联硼酸频哪醇酯催化的芳基乙烯全氟烷基吡啶化反应

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

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