Application of N-Alkyl Amines as Versatile Building Blocks in Oxidative Coupling Reactions

doi:10.6023/cjoc202009034

Abstract

The oxidative functionalization of N-alkylamines is one of the most direct and versatile strategies for the formation of C—C and C-heteroatom bonds. In recent years,N-alkylamines as multifunctional blocks have made great progress in cross- dehydrogenation-coupling (CDC) reactions. The recent progress in the application of N-alkylamines is summarized on the basis of different roles in oxidative coupling reactions.

Key words: N-alkylamines, N,N-dimethylamine, tetrahydroisoquinoline, cross-dehydrogenative-coupling reaction

Cite this article

Yuan Chen, Lijing Xia, Yiting Chang, Wuzhen Ma, Bin Wang. Application of N-Alkyl Amines as Versatile Building Blocks in Oxidative Coupling Reactions[J]. Chinese Journal of Organic Chemistry, 2021, 41(5): 1851-1877.

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Fig. & Tab. 46

Scheme 1. Copper-catalyzed CDC reaction of TIHQs and nitroalkanes

Scheme 2. PhI(OAc)2-mediated CDC reaction of tertiary amines

Scheme 3. Trifluoromethylation of TIHQs

Scheme 4. Mechanism for the Cu-catalyzed reaction of THIQs

Scheme 5. VO(acac)2-promoted CDC reaction of THIQs

Scheme 6. AuNPore-catalyzed CDC reactions of THIQs

Scheme 7. Tropylium salt-mediated reaction

Scheme 8. Trichloromethylation of tertiary amines

Scheme 9. Asymmetric CDC reaction between N-phenyl THIQs and ketones

Scheme 10. Synthesis of tetrahydroquinolines

Scheme 11. Dehydrogenative [4+2] intramolecular cycloaddition of tertiary anilines and enamides

Scheme 12. Reaction of arylboronic acid and THIQs

Scheme 13. Reaction of N-heterocycles and N,N-dimethyl- anilines

Scheme 14. FeCl3-catalyzed aerobic oxidation of tertiary anilines

Scheme 15. Metal-free CDC reaction of THIQs with I2/TBHP or I2/O2

Scheme 16. Asymmetric synthesis of 2-substituted-tetrahydro- isoquinolin-1-yl glycines

Scheme 17. Oxidative cross-dehydrogenative coupling between N-aryl tetrahydroisoquinolins and 5H-oxazol-4-ones

Scheme 18. 2D-MoS2-photocatalyzed CDC reaction of TIHPs

Scheme 19. Amidation of tertiary amines

Scheme 20. N-Alkylation and C(3)-acylation of indoles

Scheme 21. Synthesis of α-aminophosphonates

Scheme 22. Synthesis of the methylene-bridged bis-1,3- dicarbonyl derivatives

Scheme 23. Intramolecular dehydrogenative coupling reaction

Scheme 24. Rearrangement of propargylic amines

Scheme 25. Intramolecular cyclization for synthesis of acylated indoles

Scheme 26. Synthesis of 3-aroylindoles

Scheme 27. Synthesis of multisubstituted benzimidazoles

Scheme 28. Synthesis of α-(acyloxy)-β-amino ketones or α,β-diamino ketones

Scheme 29. Transformation using alkyl and aryl halides activated via α-aminoalkyl radical-mediated XAT

Scheme 30. Metal-free visible-light induced CDC of tertiary amines with diazo compounds

Scheme 31. [4+2] Cycloaddition of N-aryl tetrahydroisoquinolines with crotonaldehyde

Scheme 32. Iron-catalyzed α-C—H alkylation of N-methylaniline

Scheme 33. Cu(I)-catalyzed amidation/imidation of N-arylgly- cine ester derivatives

Scheme 34. C―H bond functionalization of allylbenzamides

Scheme 35. Ru-catalyzed indole formylation

Scheme 36. C(3)-formylation of indole

Scheme 37. Synthesis of imines from secondary amines

Scheme 38. Synthesis of oxazoles from benzylamines and aryl alkenes

Scheme 39. Synthesis of imidazo[1,5-a]pyridines

Scheme 40. Copper-promoted double oxidative C-H amination

Scheme 41. Synthesis of oxazoles through a Cu-mediated aerobic oxidative dehydrogenative annulation

Scheme 42. Synthesis of benzimidazole and N-benzylidene- benzylamines

Scheme 43. Pd-catalyzed deamination and cyclization of benzylamine with iodoarenes

Scheme 44. Deamination and condsention of benzylamines with N,N-dimethylaniline derivatives

Scheme 45. Deamination and coupling reaction of benzylamine

Scheme 46. Deamination and cyclization of benzylamines

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