甲苯及其衍生物苄位C(sp3)—H键官能团化反应研究进展

doi:10.6023/cjoc202201027

摘要/Abstract

甲苯是从石油和天然气中提取的烷基芳烃, 是化学工业中最廉价和最容易获得的材料之一. C—H键官能团化在合成各种生物活性物质中具有重要作用, 由于甲苯苄位碳氢键键能较高, 惰性碳氢键活化一直是该领域研究难点. 因此, 发展简便、高效的方法催化活化甲苯苄位C(sp³)—H键构建C—C和C—X键成为近年研究热点之一. 根据不同反应分类, 综述了近十年在不同催化条件下甲苯苄位C(sp³)—H键官能团化反应研究进展, 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: 甲苯, C(sp³)—H键活化, 惰性, 选择性催化, C—X键形成

Toluene derivatives are alkyl aromatic hydrocarbons derived from oil and natural gas and are among the cheapest and most readily available materials for the chemical industry. C—H functionalization is important for the synthesis of various bioactive substances, and inert benzylic hydrocarbon bond activation has long been a big challenge in this field due to the high hydrocarbon bond energy. Therefore, the development of simple and efficient methods for C—C and C—X bonds formation has been demonstrated as one of the hot topics by activating the benzylic C(sp³)—H bonds in recent years. The progress in benzylic C(sp³)—H functionalization of toluene and its derivatives under different catalytic conditions in the past decade is summarized according to different reaction classifications. The reaction substrate compatibility, mechanism, applications, advantages and limitations in this field are also discussed in detail.

Key words: toluene, C(sp³)—H bond activation, inert, selective catalysis, C—X bonds formation

引用此文

蔡晨怡, 邹东. 甲苯及其衍生物苄位C(sp³)—H键官能团化反应研究进展[J]. 有机化学, 2022, 42(6): 1586-1608.

Chenyi Cai, Dong Zou. Recent Progress in Benzylic C(sp³)—H Functionalization of Toluene and Its Derivatives[J]. Chinese Journal of Organic Chemistry, 2022, 42(6): 1586-1608.

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图/表 59

图1. 常见的含C(sp3)—H键化合物及其pKa值

Figure 1. Common C(sp3)—H bond-containing compounds and their pKa values

图式1. 甲苯衍生物苄位C(sp3)—H键活化反应分类

Scheme 1. Classification of C(sp3)—H bond activation reactions at the benzyl position of toluene derivatives

图式2. 1,3-二羰基化合物的苄基化反应

Scheme 2. Benzylation of 1,3-dicarbonyl compounds

图式3. 钯催化的多米诺碳钯化/C(sp3)—C(sp3)键过程

Scheme 3. Pd-Catalyzed domino carbopalladation/C(sp3)—C(sp3) bond-forming process

图式4. 丙烯酰胺的苄基化反应

Scheme 4. Benzylation reaction of acrylamides

图式5. 肉桂酰胺的苄基化反应

Scheme 5. Benzylation reaction of cinnamamides

图式6. N-Ts靛红与甲苯及其衍生物的对映选择性偶合

Scheme 6. Enantioselective coupling of N-tosyl isatins with toluene and its derivatives

图式7. 甲苯衍生物的选择性苄位C—H键活化

Scheme 7. Selective benzylic C—H functionalization of toluene derivatives

图式8. 甲苯衍生物与重氮羧酸酯的烯烃烷基化

Scheme 8. Olefin alkylation of toluene derivatives with diazocarboxylic acid esters

图式9. 初级C(sp3)—H的选择性活化

Scheme 9. Selective primary C(sp3)—H activation

图式10. 甲苯和醛的氨基苄基化反应

Scheme 10. Aminobenzylation of toluene and aldehydes

图式11. 甲苯和亚胺的氨基苄基化反应以及甲苯与烯烃的烷基化反应

Scheme 11. Aminobenzylation of toluene and imines and alkylation of toluene with olefins

图式12. 异氰化物与芳烃碘的环化反应

Scheme 12. Cyclization of isocyanides with iodobenzenes

图式13. Pd催化三氟乙酰亚氨基氯化物C(sp3)—H功能化

Scheme 13. Pd-catalyzed C(sp3)—H functionalization of trifluoroacetimidoyl chlorides

图式14. 腈与甲基芳烃的环化反应

Scheme 14. Cyclization of nitriles with toluene derivatives

图式15. 芴衍生物的合成

Scheme 15. Synthesis of fluorene derivatives

图式16. 甲苯与溴苯的芳基化反应

Scheme 16. Aromatization of toluene with bromobenzenes

图式17. 芳基硼酸酯和甲苯的芳基化反应

Scheme 17. Aromatization of arylboronic acid esters with toluene

图式18. 芳基硼酸和芳基乙烷的芳基化反应

Scheme 18. Aromatization of arylboronic acids with aryl ethanes

图式19. 吲哚喹唑啉酮衍生物的合成

Scheme 19. Synthesis of indoloquinazolinones

图式20. Ni催化的甲苯衍生物和吲哚C(sp2)—H/C(sp3)—H氧化偶联

Scheme 20. Ni-catalyzed C(sp2)—H/C(sp3)—H oxidative coupling of indoles with toluene derivatives

图式21. Co催化未活化苯甲酰胺和甲苯衍生物偶联

Scheme 21. Co-catalyzed coupling of unactivated benzamides and toluene derivatives

图式22. CO2催化羧化C(sp3)—H的顺序反应 CO2催化羧化C(sp3)—H的顺序反应

Scheme 22. Sequential protocol for C(sp3)—H carboxylation with CO2

图式23. 邻烷基苯基酮与CO2的光驱动羧化

Scheme 23. Light-driven carboxylation of o?alkylphenyl ketones with CO2

图式24. 钯催化的苄基C—H键的氧化羰基化

Scheme 24. Palladium-catalyzed oxidative carbonylation of benzylic C—H bonds

图式25. Pd催化C(sp3)—H键合成吲哚酮衍生物

Scheme 25. Pd-catalyzed C(sp3)—H bond activation for the synthesis of indolone derivatives

图式26. 光诱导C(sp3)—H键与异氰酸酯氨基甲酰化作用

Scheme 26. Photoinduced carbamoylation of C(sp3)—H bonds with isocyanates

图式27. 甲苯和Weinreb酰胺的苄基芳酰化反应

Scheme 27. Benzylic aroylation of toluenes with Weinreb amides

图式28. 甲苯和N-酰基吡咯的苄基芳酰化反应

Scheme 28. Benzylic aroylation of toluenes with N-acyl pyrroles

图式29. Cu(II)催化醛和烷基苯合成苄基酯

Scheme 29. Cu(II)-catalyzed synthesis of benzyl esters from aldehydes and alkylbenzenes

图式30. 在无金属催化条件下烷基苯合成苄基酯

Scheme 30. Synthesis of benzylic esters from alkyl benzenes under metal-free conditions

图式31. 醇或磷酸盐与甲苯的无过渡金属氧化酯化

Scheme 31. Transition metal free oxidative esterification of toluene with alcohols or phosphites

图式32. 羧酸与甲苯的酯化反应

Scheme 32. Esterification of carboxylic acids with toluene

图式33. 邻位甲基与羧酸的内酯化反应

Scheme 33. Lactonization of o-methyl with carboxylic acids

图式34. 过氧苯甲酸叔丁酯与甲苯的酯化反应

Scheme 34. Esterification of tert-butyl peroxybenzoates with toluene

图式35. 丙烯醇与甲苯的酯化反应

Scheme 35. Esterification of allyl alcohols with toluene

图式36. 肉桂酸与甲苯衍生物的烯烃化反应

Scheme 36. Olefination of cinnamic acids with toluene derivatives

图式37. 烯酮与甲基芳烃的α-苄基化反应

Scheme 37. α-Benzylation of enones with toluene derivatives

图式38. 钯催化的甲苯衍生物烯烃化环化反应

Scheme 38. Pd-catalyzed olefinic cyclization of toluene derivatives

图式39. 磺酰胺与甲基芳烃的胺化反应

Scheme 39. Amination of sulfonamides with toluene derivatives

图式40. N-氟苯磺酰胺与甲基芳烃的胺化反应

Scheme 40. Amination of N-fluorobenzenesulfonimides with toluene derivatives

图式41. 苯并三唑与甲基芳烃的胺化反应

Scheme 41. Amination of 1H-benzotriazoles with toluene derivatives

图式42. 碘化钾催化的甲基芳烃胺化反应

Scheme 42. KI-catalyzed amination of toluene derivatives

图式43. 邻氨基苯磺酰胺与甲基芳烃的胺化反应

Scheme 43. Amination of toluene derivatives with o-amino- benzenesulfonamide

图式44. 硝基芳烃与甲基芳烃的胺化反应

Scheme 44. Amination of nitroarenes with toluene derivatives

图式45. 异喹啉与甲基芳烃的氧化胺化反应

Scheme 45. Oxidative amination of isoquinolines with toluene derivatives

图式46. TcesNH2与甲基芳烃的胺化反应 TcesNH2与甲基芳烃的胺化反应

Scheme 46. Amination of TcesNH2 with toluene derivatives

图式47. 氨基芳烃与甲基芳烃的胺化反应

Scheme 47. Amination of aminoaromatics with toluene derivatives

图式48. 分子内胺化合成异吲哚酮

Scheme 48. Synthesis of isoindolones by intramolecular amination

图式49. 硫醇与甲基芳烃的硫化反应

Scheme 49. Sulfurization of mercaptans with toluene derivatives

图式50. AgSCF3与甲基芳烃的氧化硫化反应

Scheme 50. Oxidative sulfurization of AgSCF3 with toluene derivatives

图式51. K-PHI介导的甲基芳烃硫化反应

Scheme 51. K-PHI-mediated sulfurization of toluene derivatives

图式52. Li/K-TMP催化的甲基芳烃硅基化反应

Scheme 52. Li/K-TMP-catalyzed silylation of toluene derivatives

图式53. 钌络合物催化的甲基芳烃硅基化反应

Scheme 53. Ruthenium-catalyzed silylation of toluene derivatives

图式54. Oxone催化的甲基芳烃溴化反应

Scheme 54. Oxone-catalyzed bromination of toluene derivatives

图式55. SelectfluorTM催化的甲基芳烃氟化反应

Scheme 55. SelectfluorTM-catalyzed fluorination of toluene derivatives

图式56. 钴催化的C(sp3)—H键氟化反应

Scheme 56. Co-catalyzed fluorination of C(sp3)—H bonds

图式57. 甲苯的硒醚化和硫脂化反应

Scheme 57. Selenide etherification and thioesterification of toluene

图式58. UiO-Co催化的C(sp3)—H键官能团化反应

Scheme 58. UiO-Co-catalyzed functionalization of C(sp3)—H bonds

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甲苯及其衍生物苄位C(sp³)—H键官能团化反应研究进展

Recent Progress in Benzylic C(sp³)—H Functionalization of Toluene and Its Derivatives

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