可见光诱导α-氨基酸衍生物脱羧偶联反应研究进展

doi:10.6023/cjoc202110020

摘要/Abstract

氨基酸是一类来源丰富、廉价易得并且绿色环保的生物质原料, 可用于合成高附加值生物活性分子、药物和功能材料等, 还可作为有机催化剂或金属配体用于不对称合成转化. 可见光是绿色清洁的可再生资源, 具有丰富易得、环境友好和应用潜力巨大等优点, 其催化的反应条件温和且化学选择性好. 利用可见光催化α-氨基酸衍生物脱羧偶联构建种类丰富的含氮化合物是一种极具吸引人的合成策略. 综述了近年来光催化α-氨基酸衍生物脱羧偶联反应的研究进展.

关键词: 可见光, 氨基酸衍生物, 脱羧偶联, 自由基, 官能化

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

引用此文

胡家榆, 祝志强, 谢宗波, 乐长高. 可见光诱导α-氨基酸衍生物脱羧偶联反应研究进展[J]. 有机化学, 2022, 42(4): 978-1001.

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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图/表 54

图式1. 可见光诱导α-氨基酸脱羧芳基化

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

图式2. 光催化α-氨基酸与烯基砜脱羧偶联

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

图式3. 光催化α-氨基酸与烯烃衍生物共轭加成

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

图式4. 光促进左旋肌胺合成

Scheme 4. Synthesis of L-ossamine by photocatalysis

图式5. 光催化α-氨基酸脱羧炔基化

Scheme 5. Photocatalytic decarboxylative alkynylation of α- amino acids

图式6. 光催化α-氨基酸脱羧氰基化

Scheme 6. Photocatalytic decarboxylative cyanation of α-amino acids

图式7. 多肽分子内脱羧偶联

Scheme 7. Intramolecular decarboxylative coupling of peptides

图式8. 光催化α-氨基酸与α,β-不饱和羰基化合物脱羧偶联

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

图式9. 光催化α-氨基酸与活化烯烃脱羧自由基加成

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

图式10. 光促进活性氨基酸酯分子内脱羧胺化

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

图式11. 光催化α-氨基酸与偕二氟烯烃脱羧单氟烯基化

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

图式12. 可见光介导α-氨基酸脱羧胺化

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

图式13. 可见光与酶促进氨烷基化

Scheme 13. Visible-light and enzymatic aminoalkylation

图式14. 酶和光共催化α-氨基酸脱羧偶联环化

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

图式15. 可见光促进α-氨基酸分子内脱羧偶联环化

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

图式16. 光催化氨基酸脱羧偶联合成烷基硼酸酯

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

图式17. 光催化α-氨基酸衍生物脱羧Povarov反应

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

图式18. 光氧化还原催化α-氨基酸脱羧烷基化

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

图式19. 天然蛋白脱羧烷基化

Scheme 19. Decarboxylative alkylation of native proteins

图式20. 咪唑并[1,2-a]吡啶α-氨烷基化

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

图式21. 不对称自由基偶联合成β-氨基酮

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

图式22. 光催化α-氨基酸[3+2]环加成

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

图式23. 可见光诱导异噁唑烷类化合物合成

Scheme 23. Visible-light-induced synthesis of isoxazolidines

图式24. 可见光促进烯丙基胺衍生物合成

Scheme 24. Visible light-promoted synthesis of allylamine derivatives

图式25. 可见光催化喹喔啉-2(1H)-酮与脂肪羧酸脱羧偶联

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

图式26. 光催化α-氨基酸非均相脱羧偶联

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

图式27. 可见光催化2-取代哌嗪合成

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

图式28. 多组分脱羧自由基偶联可控合成二胺或咪唑啉衍生物

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

图式29. 可见光催化β-氨基醇合成

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

图式30. 光催化合成β-氨基羟胺

Scheme 30. Photocataltic synthesis of β-amino hydroxylamines

图式31. 可见光促进多组分串联合成γ-氨基醇

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

图式32. 光催化烯烃与α-氨基酸脱羧双官能团化

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

图式33. 光催化苯乙烯与甘氨酸钠的α-氨基甲基羧化

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

图式 34. 光催化合成多取代吡咯

Scheme 34. Photocatalytic synthesis of polysubstituted pyrroles

图式35. 光催化α-氨基酸脱羧偶联环化构建1,2,4-三氮唑烷

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

图式36. 可见光诱导烯酰胺C—H烷基化

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

图式37. 可见光促进芳杂环C—H氨烷基化

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

图式38. 光与镍共催化α-氨基酸脱羧芳基化

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

图式39. 光与镍共催化α-氨基酸对映选择性脱羧芳基化

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

图式40. 光与铜协同促进活性α-氨基酸酯脱羧炔基化

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

图式41. 光与镍共催化α-氨基酸与苯基磺酸酯脱羧偶联

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

图式42. 光与金属共催化α-氨基酸分子内脱羧

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

图式43. On-DNA脱羧芳基化

Scheme 43. On-DNA decarboxylative arylation

图式44. 光和镍共催化三组分反应合成烯烃衍生物

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

图式45. 光氧化还原/布朗斯特酸共催化N-杂芳烃与α-氨基酸脱羧偶联

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

图式46. 共催化Mannich反应和Heck反应

Scheme 46. Dual catalytic Mannich and Heck reaction

图式47. 光和布朗斯特酸共催化N-杂芳烃与α-氨基酸不对称脱羧偶联

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

图式48. α-氨基酸脱羧偶联构建异喹啉取代手性胺

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

图式49. 光与手性磷酸共催化α-氨基酸不对称自由基脱羧偶联

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

图式50. α-氨基酸与活性酮不对称自由基偶联反应

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

图式51. α-氨基酸与α-卤代酮不对称自由基脱羧偶联

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

图式52. α-氨基酸脱羧不对称偶联构建手性γ-氨基酮

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

图式53. 对映选择性脱羧Povarov反应

Scheme 53. Enantioselective decarboxylative Povarov reaction

图式54. 光与手性磷酸盐共催化不对称Friedel-Crafts反应

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

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