光氧化还原催化的C-糖基化反应

doi:10.6023/cjoc202408003

摘要/Abstract

光氧化还原催化已成为构建C-糖苷的一种多功能、高效的反应手段, 为合成结构多样的C-糖基化合物提供了新途径. 利用这一温和绿色的合成工具已经合成了官能团多样化的C-糖苷类化合物, 对糖类化学研究产生了促进性的影响. 对近年来利用光氧化还原催化构建C-糖苷的反应类型进行分类和系统总结, 目前利用光氧化还原催化构建C-糖苷的反应模式分为传统光催化剂参与的氧化还原反应、激发态过渡金属参与的氧化还原反应、光氧化还原/过渡金属协同催化的偶联反应和光激发电子供体-受体复合物介导的反应四种类型. 此外, 还对涉及的反应机理也进行了较为详细的讨论.

关键词: 光氧化还原催化, 糖苷化, C-糖苷化, 糖基自由基

Photoredox catalysis has become a multifunctional and efficient reaction method for constructing C-glycosides, which provides a new pathway for synthesizing complicated carbohydrate. This mild green synthetic tool has been used to synthesize C-glycosides with diverse functional groups, which has a promoting effect on carbohydrate chemistry research. The types of C-glycosidic reactions constructed through photoredox catalysis, which are categorized as a conventional photoredox catalysis, redox reactions involving excited-state transition metals, dual photoredox/transition metal (TM)-catalyzed cross- coupling reaction and light-excited electron donor-acceptor complex, are systematically summarized. In addition, a detailed description of the reaction mechanisms is provided.

Key words: photoredox catalysis, glycosylation, C-glycosylation, glycosyl radical

引用此文

李晨, 焦毅, 施笑然, 杨毅强, 俞寿云. 光氧化还原催化的C-糖基化反应[J]. 有机化学, 2025, 45(5): 1423-1459.

Chen Li, Yi Jiao, Xiaoran Shi, Yiqiang Yang, Shouyun Yu. Photoredox-Catalyzed C-Glycosylation Reactions[J]. Chinese Journal of Organic Chemistry, 2025, 45(5): 1423-1459.

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图/表 52

图1. 代表性C-糖苷类化合物

Figure 1. Representative compounds of C-glycosides

图式1. 糖自由基介导的C-糖苷键构建

Scheme 1. Glycosyl radical-mediated C-glycosylation

图式2. 光氧化还原催化C-糖基化反应的主要途径

Scheme 2. Main pathways of photoredox-catalyzed C-glycosylation reaction

图式3. 可见光介导的糖基溴化物与烯烃的烷基化

Scheme 3. Visible-light-mediated alkylation reaction of glycosyl bromides with olefins

图式4. 光介导的脱氟偕-二氟烷基化反应

Scheme 4. Photomediated defluorinative gem-difluoroallylation reaction

图式5. 糖基溴化物对多肽Dha的糖基化修饰

Scheme 5. Glycosylation of peptide Dha by glycosyl bromides

图式6. α-C-糖基丙氨酸类似物的合成

Scheme 6. Synthesis of α-C-glycosyl alanine analogues

图式7. 可见光诱导活化烯烃的糖芳基化

Scheme 7. Visible-light-induced glycoarylation of activated olefins

图式8. 醇的C-烷基化

Scheme 8. C-Alkylation of alcohols

图式9. 无保护单糖的位点选择性烷基化

Scheme 9. Site-selective alkylation of unprotected monosaccharides

图式10. 去甲酰化1,4-加成合成5'-磷酸核苷的5'-卡巴类似物

Scheme 10. Deformylative 1,4-addition to synthesize 5'-carba analogs of nucleoside 5'-phosphates

图式11. C-糖基氨基酸的合成

Scheme 11. Synthesis of C-glycosyl amino acids

图式12. 糖基NHP酯的立体化学反转脱羧光烷基化

Scheme 12. Decarboxylative photoalkylation of glycosyl NHP esters via inversion of stereochemistry

图式13. 光氧化还原催化位点和立体选择性C—H烷基化

Scheme 13. Photoredox catalytic site- and stereoselective C—H alkylations

图式14. 吡喃糖衍生物的光氧化还原催化区域选择性C—H烷基化

Scheme 14. Photoredox catalytic regioselective C—H alkylation of fructopyranose derivative

图式15. 葡萄糖基亚磺酸盐和迈克尔受体的C-糖基化反应

Scheme 15. C-Glycosylation of glycosyl sulfinates and Michael acceptors

图式16. 光氧化还原催化合成糖类-DNA偶联物

Scheme 16. Photoredox-catalyzed synthesis of carbohydrate-DNA conjugates

图式17. 糖基酯的异头C—O键均裂立体选择性C-烷基糖基化

Scheme 17. Stereoselective alkyl C-glycosylation of glycosyl esters via anomeric C—O bond homolysis

图式18. 位点选择性无保护糖的C-烷基糖基化

Scheme 18. Site-selective C-alkylation of unprotected sugars

图式19. 糖类化物的直接C—H三氟甲基化

Scheme 19. Direct C—H trifluoromethylation of glycal

图式20. 2-乙酰氧基烯糖还原氟烷基化反应

Scheme 20. Reductive fluoroalkylation of 2-acetoxyglycas

图式21. 烯糖化物的直接C—H三氟甲基化

Scheme 21. Direct C—H trifluoromethylation of glycals

图式22. 可见光催化下未活化糖基溴的烯基化反应

Scheme 22. Alkenylation of unactivated glycosyl bromides through visible light photocatalysis

图式23. 光还原催化糖基二氢吡啶(DHPs)和乙烯基苯碘氧基物的乙烯基化反应

Scheme 23. Photoredox-catalyzed vinylations of glycosyl-dihydropyridines (DHPs) and vinylbenziodoxol(on)es

图式24. 光氧化还原催化的糖溴还原偶联制备C-炔基糖苷

Scheme 24. Photoredox-catalyzed reductive coupling of glycosyl bromides to access C-alkynyl glycosides

图式25. 光催化脱羧立体选择性C-糖基炔基化

Scheme 25. Stereoselective C-glycosylation by photocatalytic decarboxylative alkynylation

图式26. 4-糖基二氢吡啶合成杂芳基C-糖苷

Scheme 26. Synthesis of heteroaryl C-glycosides via 4-glycosyl-dihydropyridines

图式27. 可见光下由糖基溴和杂芳烃合成C-核苷类似物

Scheme 27. Synthesis of C-nucleoside analogues from glycosyl bromides and heteroarenes under visible light

图式28. 联苯异氰酸酯/2-异氰芳基硒醚/硫醚与糖基溴的C-杂芳基糖基化

Scheme 28. C-heteroaryl glycosylation of biphenyl isocyanides/ 2-isocyanoaryl selenoethers/thioethers with glycosyl bromides

图式29. 可见光诱导钯催化的Heck型自由基反应构建C-烯基化糖苷

Scheme 29. Visible-light-induced Pd-catalyzed Heck-type radical reactions to construct C-alkenylation glycosides

图式30. 激发态钯催化的构建C-酮基化糖苷

Scheme 30. Excited-state palladium-catalyzed methods to construct C-ketonylation glycosides

图式31. 可见光促进和铜催化的立体选择性C-糖基化

Scheme 31. Visible-light-promoted and Cu-catalyzed stereoselective C-glycosylation

图式32. 镍/光氧化还原双催化合成高度官能化的芳基糖

Scheme 32. Synthesis of highly functionalized arylated saccharides through nickel/photoredox dual catalysis

图式33. 镍/光氧化还原催化脱羧合成芳基/杂芳基C-核苷类衍生物

Scheme 33. Synthesis of aryl/ heteroaryl-C-nucleosides via Ni/photoredox-catalyzed decarboxylation

图式34. 糖基三氟硼酸盐的镍/光氧化还原双催化偶联反应

Scheme 34. Ni/photoredox dual catalytic coupling of glycosyl trifluoroborates

图式35. 镍/光氧化还原双催化的醇类脱氧芳基化

Scheme 35. Ni/photoredox dual catalytic deoxygenative arylation of alcohols

图式36. 镍/光氧化还原双催化糖基氯代物与芳基溴的还原偶联

Scheme 36. Ni/photoredox dual catalytic reductive cross-coupling of glycosyl chlorides and aryl bromides

图式37. 镍/光氧化还原双催化糖基氯代物与芳基溴的还原偶联

Scheme 37. Ni/photoredox dual catalytic reductive cross-coupling of glycosyl chlorides and aryl bromides

图式38. 3-甲氧羰基-2-碘-1H-吲哚与吡喃溴的镍/光氧化双催化还原交叉偶联

Scheme 38. Ni/photoredox dual catalytic reductive cross-coupling of pyranosyl bromides with 3-methoxycarbonyl-2-iodo-1H-indoles

图式39. 光氧化还原/镍催化交叉偶联合成无保C-芳基糖苷

Scheme 39. Synthesis of unprotected aryl C-glycosides by photoredox/Ni-catalysed cross-coupling

图式40. 区域选择性镍催化仲α-烷氧基前体的光氧化烯丙基化反应

Scheme 40. Regioselective nickel-catalyzed photoredox allylation of secondary α-alkoxy radical precursors

图式41. 烯丙醇的光还原/镍双催化Tsuji-Trost反应

Scheme 41. Photoredox/nickel dual catalytic Tsuji-Trost reaction of allylic alcohols

图式42. 光氧化还原/铜双催化反应构建C-糖苷和糖肽

Scheme 42. Photoredox/Cu dual catalytic reaction for construction of C-linked glycosides and glycopeptides

图式43. 光氧化还原/镍双催化呋喃糖羧酸和末端炔烃合成炔基C-核苷

Scheme 43. Synthesis of alkynyl C-nucleosides from furanosyl carboxylic acids and terminal alkynes under photoredox/nickel dual catalysis

图式44. Ni/光氧化还原双催化合成C-酰基糖苷

Scheme 44. Synthesis of C-acyl glycosides through Ni/photoredox dual catalysis

图式45. Ni/光氧化还原双催化合成C-酰基糖苷的机理

Scheme 45. Mechanism of the synthesis of C-acyl glycosides through Ni/photoredox dual catalysis

图式46. 镍介导EDA复合物光活化制备非异头C-酰基糖

Scheme 46. Nickel-mediated preparation of nonanomeric C-acyl-saccharides through EDA complex photoactivation

图式47. Ni/光氧化还原双催化合成酰胺连接的C-糖基氨基酸和肽

Scheme 47. Synthesis of amide linked C-glycosyl amino acids and peptides throught Ni/photoredox dual catalysis

图式48. 可见光促进的EDA复合物实现1,4-DHP修饰的吡喃半乳糖的吡啶官能化

Scheme 48. Visible-light promoted EDA complex to enable pyridine functionalization of galactopyranose modified with 1,4-DHPs

图式49. 糖基亚砜作为自由基前体及其在吡啶衍生物合成中的应用

Scheme 49. Glycosyl sulfoxides as radical precursors and their use in the synthesis of pyridine derivatives

图式50. 可见光活化促使杂芳基糖基砜底物的脱硫活性与亲电试剂偶联

Scheme 50. Visible light activation enabled desulfonylative of heteroaryl glycosyl sulfone substrates to couple with electrophiles

图式51. 天然糖类自由基的直接官能团化

Scheme 51. Direct radical functionalization of native sugars

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