Recent Advances in Visible-Light-Induced Decarboxylative Coupling Reactions of α-Amino Acid Derivatives

doi:10.6023/cjoc202110020

Abstract

Amino acids are an important class of biomass raw materials, which are widely used as starting materials to synthetize bioactive molecules, drugs and functional materials, and are also useful as organic catalysts or metal ligands for asymmetric synthesis. Visible-light-induced organic transformation has attracted enormous interest due to its intrinsic characteristics of sustainability and green chemistry. The use of visible-light to promote decarboxylative coupling of α-amino acids to construct various nitrogen-containing compounds has been considered as an attractive synthetic strategy. This review highlights the recent progress in photocatalytic decarboxylative coupling reactions of α-amino acid derivatives with various partners.

Key words: visible-light, amino acid derivatives, decarboxylative coupling, radical, functionalization

Cite this article

Jiayu Hu, Zhiqiang Zhu, Zongbo Xie, Zhanggao Le. Recent Advances in Visible-Light-Induced Decarboxylative Coupling Reactions of α-Amino Acid Derivatives[J]. Chinese Journal of Organic Chemistry, 2022, 42(4): 978-1001.

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Fig. & Tab. 54

Scheme 1. Visible-light-induced decarboxylative arylation of α-amino acids

Scheme 2. Photocatalytic decarboxylative coupling of α-amino acids with alkenyl sulfones

Scheme 3. Photocatalytic conjugate addition of α-amino acids with alkene derivatives

Scheme 4. Synthesis of L-ossamine by photocatalysis

Scheme 5. Photocatalytic decarboxylative alkynylation of α- amino acids

Scheme 6. Photocatalytic decarboxylative cyanation of α-amino acids

Scheme 7. Intramolecular decarboxylative coupling of peptides

Scheme 8. Photocatalytic decarboxylative coupling of α-amino acids with α,β-unsaturated carbonyl compounds

Scheme 9. Photocatalytic decarboxylative radical addition of α-amino acids with activated alkenes

Scheme 10. Light-promoted intramolecular decarboxylative amination of activated α-amino acid esters

Scheme 11. Visible light photocatalytic decarboxylative monofluoroalkenylation of α-amino acids with gem-difluoroalkenes

Scheme 12. Visible light-mediated decarboxylative amination of α-amino acids

Scheme 13. Visible-light and enzymatic aminoalkylation

Scheme 14. Decarboxylative coupling cyclization of α-amino acids by photocatalysis and enzymatic catalysis

Scheme 15. Visible-light-promoted intramolecular decarboxylative coupling cyclization of α-amino acids

Scheme 16. Photocatalytic decarboxylative coupling of amino acids to γ-amino boronic esters

Scheme 17. Photocatalytic decarboxylative Povarov reaction of α-amino acid derivatives

Scheme 18. Photoredox catalytic decarboxylative alkylation of α-amino acids

Scheme 19. Decarboxylative alkylation of native proteins

Scheme 20. α-Amino alkylation of imidazo[1,2-a]pyridines

Scheme 21. Asymmetric free radical coupling for synthesis of β-amino ketones

Scheme 22. Photocatalytic [3+2] cycloaddition of α-amino acids

Scheme 23. Visible-light-induced synthesis of isoxazolidines

Scheme 24. Visible light-promoted synthesis of allylamine derivatives

Scheme 25. Visible-light-catalyzed cross-decarboxylative coupling of quinoxalin-2(1H)-ones with carboxylic acids

Scheme 26. Heterogeneous photocatalytic decarboxylative coupling of α-amino acids

Scheme 27. Synthesis of 2-substituted piperazines by visible-light photocatalysis

Scheme 28. Controllable synthesis of diamine or imidazoline derivatives by multicomponent decarboxylative radical coupling

Scheme 29. Synthesis of β-amino alcohols by visible-light photocatalysis

Scheme 30. Photocataltic synthesis of β-amino hydroxylamines

Scheme 31. Visible-light-promoted synthesis of γ-amino alcohols by multicomponent cascade

Scheme 32. Photocatalytic decarboxylative bifunctionalization of alkenes with α-amino acids

Scheme 33. Photoredox-catalyzed α-aminomethyl carboxylative of styrenes with sodium glycinates

Scheme 34. Photocatalytic synthesis of polysubstituted pyrroles

Scheme 35. Photocatalytic decarboxylative of α-amino acids to construct 1,2,4-triazolidine

Scheme 36. Visible-light-induced C—H functionalization of enamides

Scheme 37. Visible-light-promoted heterocycles C—H aminoalkylation

Scheme 38. Merging photoredox with nickel catalysis: coupling of α-carboxyl sp3-carbons with aryl halides

Scheme 39. Enantioselective decarboxylative arylation of α-amino acids by visible-light and nickel catalysis

Scheme 40. Decarboxylative alkynylation of activated α-amino acid esters by visible-light and copper catalysis

Scheme 41. Decarboxylative coupling of α-amino acids and phenyl sulfonate by visible-light and nickel catalysis

Scheme 42. Intramolecular decarboxylative of α-amino acids by visible-light and metal catalysis

Scheme 43. On-DNA decarboxylative arylation

Scheme 44. Synthesis of alkene derivatives by three-component reaction through visible-light and nickel catalysis

Scheme 45. Photoredox/Brønsted acid co-catalysis enabling decarboxylative coupling of N-heteroarenes with α-amino acids

Scheme 46. Dual catalytic Mannich and Heck reaction

Scheme 47. Asymmetric decarboxylative coupling of N-heteroarenes with α-amino acids by photoredox and Brønsted acid catalysis

Scheme 48. Decarboxylative of α-amino acids to construct isoquinoline-substituted chiral amines

Scheme 49. Asymmetric decarboxylative free-radical coupling of α-amino acids by visible-light and chiral phosphoric acid

Scheme 50. Asymmetric free radical coupling of α-amino acids with activated ketones

Scheme 51. Asymmetric decarboxylative coupling of α-amino acids with α-halogenated ketones

Scheme 52. Asymmetric decarboxylative coupling of α-amino acid to construct chiral γ-amino ketones

Scheme 53. Enantioselective decarboxylative Povarov reaction

Scheme 54. Visible-light and chiral phosphate-promoted asymmetric Friedel-Crafts reaction

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