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

doi:10.6023/cjoc202201027

Abstract

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

Cite this article

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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Fig. & Tab. 59

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

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

Scheme 2. Benzylation of 1,3-dicarbonyl compounds

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

Scheme 4. Benzylation reaction of acrylamides

Scheme 5. Benzylation reaction of cinnamamides

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

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

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

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

Scheme 10. Aminobenzylation of toluene and aldehydes

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

Scheme 12. Cyclization of isocyanides with iodobenzenes

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

Scheme 14. Cyclization of nitriles with toluene derivatives

Scheme 15. Synthesis of fluorene derivatives

Scheme 16. Aromatization of toluene with bromobenzenes

Scheme 17. Aromatization of arylboronic acid esters with toluene

Scheme 18. Aromatization of arylboronic acids with aryl ethanes

Scheme 19. Synthesis of indoloquinazolinones

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

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

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

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

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

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

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

Scheme 27. Benzylic aroylation of toluenes with Weinreb amides

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

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

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

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

Scheme 32. Esterification of carboxylic acids with toluene

Scheme 33. Lactonization of o-methyl with carboxylic acids

Scheme 34. Esterification of tert-butyl peroxybenzoates with toluene

Scheme 35. Esterification of allyl alcohols with toluene

Scheme 36. Olefination of cinnamic acids with toluene derivatives

Scheme 37. α-Benzylation of enones with toluene derivatives

Scheme 38. Pd-catalyzed olefinic cyclization of toluene derivatives

Scheme 39. Amination of sulfonamides with toluene derivatives

Scheme 40. Amination of N-fluorobenzenesulfonimides with toluene derivatives

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

Scheme 42. KI-catalyzed amination of toluene derivatives

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

Scheme 44. Amination of nitroarenes with toluene derivatives

Scheme 45. Oxidative amination of isoquinolines with toluene derivatives

Scheme 46. Amination of TcesNH2 with toluene derivatives

Scheme 47. Amination of aminoaromatics with toluene derivatives

Scheme 48. Synthesis of isoindolones by intramolecular amination

Scheme 49. Sulfurization of mercaptans with toluene derivatives

Scheme 50. Oxidative sulfurization of AgSCF3 with toluene derivatives

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

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

Scheme 53. Ruthenium-catalyzed silylation of toluene derivatives

Scheme 54. Oxone-catalyzed bromination of toluene derivatives

Scheme 55. SelectfluorTM-catalyzed fluorination of toluene derivatives

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

Scheme 57. Selenide etherification and thioesterification of toluene

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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甲苯及其衍生物苄位C(sp3)—H键官能团化反应研究进展