光/电催化醚α-位官能团化研究进展

doi:10.6023/cjoc202305011

摘要/Abstract

醚类化合物由于其优异的物理化学性质广泛应用于有机化学、材料科学、生物医药等领域. 其中, 四氢呋喃/四氢噻吩及其衍生物更是构建生物活性分子和复杂的天然产物的核心骨架. 光/电催化因其符合绿色化学要求, 以及大多涉及自由基中间体的独特路径, 近年来已逐步成为化学家们合成新颖化合物的重要手段. 利用光/电催化实现醚类化合物α-位的官能团化是一种绿色、高效的合成策略. 因此, 以氧醚/硫醚为例, 综述了光/电催化醚类化合物α-位官能团化的研究进展, 并对部分机理做了详细的介绍.

关键词: 醚类化合物, 光催化, 电催化, 光电协同催化, 官能团化

Ethers are widely used in organic chemistry, materials science, biomedicine and other fields due to their excellent physicochemical properties. Among them, tetrahydrofuran/tetrahydrothiophene and their derivatives are the core backbones for building biologically active molecules and complex natural products. In recent years, photo/electrocatalysis has gradually become an important tool for chemists to synthesize novel compounds due to its compliance with the requirements of green chemistry and the unique pathway that mostly involves radical intermediates. The functionalization of α-positions of ethers using photo/electrocatalysis is a green and efficient synthetic strategy. Therefore, the research progress of photo/electro- catalytic functionalization of ether compounds at the α-position is reviewed with ether/sulfide as examples, and a detailed description of some of the mechanisms is provided.

Key words: ethers, photocatalysis, electrocatalysis, photoelectric co-catalysis, functionalization

引用此文

刘颖杰, 石岗庆, 仇格, 张鑫, 宋冬雪, 陈宁, 于淼, 许颖. 光/电催化醚α-位官能团化研究进展[J]. 有机化学, 2023, 43(8): 2664-2681.

Yingjie Liu, Gangqing Shi, Ge Chou, Xin Zhang, Dongxue Song, Ning Chen, Miao Yu, Ying Xu. Progress of α-Position Functionalization of Ethers under Photo/Electrocatalysis[J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2664-2681.

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图/表 41

图式1. 光催化杂环化合物α-C—H键烷基化反应及其反应机制

Scheme 1. Photocatalytic C-H bond alkylation reaction and its reaction mechanism

图式2. 光催化四氢呋喃的烷基化

Scheme 2. Photocatalytic alkylation of tetrahydrofuran

图式3. 光催化氮/氧杂环α-C—H键烷基化反应及其反应机制

Scheme 3. Photocatalytic α-C-H bonded alkylation of nitrogen/oxygen heterocycles and its reaction mechanism

图式4. 香豆素衍生物的合成

Scheme 4. Synthesis of coumarin derivatives

图式5. 光/镍协同催化α-C—H键芳基化反应

Scheme 5. Photochemical nickel-catalyzed C—H arylation

图式6. 光催化杂环化合物α-位肟醚化反应及其反应机理

Scheme 6. Photocatalytic α-position oxime etherification of heterocyclic compounds and its reaction mechanism

图式7. 光催化醚/酰胺的α-位烯化反应

Scheme 7. Photocatalytic α-site alkenylation of ethers/amides

图式8. 烯酮衍生物的合成

Scheme 8. Synthesis of alkenone derivatives

图式9. 2-乙烯基杂环化合物的合成及其反应机制

Scheme 9. Synthesis of 2-vinylheterocyclic compounds and reaction mechanism

图式10. 可见光诱导的2H-吲唑衍生物的合成及其反应机理

Scheme 10. Synthesis of 2H-indazole derivatives induced by visible light and their reaction mechanism

图式11. 3,3-二取代丙烯酸的合成

Scheme 11. Synthesis of 3,3-disubstituted acrylic acid

图式12. 四环苯并[4,5]咪唑并[2-c]喹唑啉类化合物的合成

Scheme 12. Tetracyclic benzo[4,5]imidazole[1,2-c]quinazoline of synthesis

图式13. 3-烷基化香豆素的合成及其反应机理

Scheme 13. Synthesis of 3-alkylated coumarin and its reaction mechanism

图式14. 量子点介导的四氢呋喃α-位烯化反应

Scheme 14. Quantum dot-mediated α-site alkenylation of tetrahydrofuran

图式15. 6-氧烷基化-1,2,4-三嗪-3,5(2H,4H)-二酮衍生物的合成及其反应机制

Scheme 15. Synthesis of 6-oxakylated-1,2,4-triazine-3,5(2H, 4H)-dione derivatives and its reaction mechanism

图式16. H2O2介导的端炔的氢化烷基化反应

Scheme 16. H2O2-mediated hydroalkylation of terminal alkynes

图式17. 醚、酰胺和脂肪醛的单氟烯化反应及其反应机理

Scheme 17. Monofluoroalkylation of ethers, amides and alipha- tic aldehydes and their reaction mechanisms

图式18. 醚、酰胺、醇和胺的α-位肟醚化反应

Scheme 18. Alpha-position oxime etherification of ethers, amides, alcohols and amines

图式19. 异喹啉衍生的光催化剂介导的C—C键偶联反应及其反应机制

Scheme 19. Isoquinoline-derived photocatalyst-mediated C—C bond coupling reaction its reaction mechanism

图式20. 光/镍双催化的氧杂环对映选择性C—H官能团化反应

Scheme 20. Enantioselective C—H functionalization of oxacycles via photo/nickel dual catalysis

图式21. 光催化α-炔基醚类衍生物的合成

Scheme 21. Photocatalytic synthesis of α-alkynyl ether derivatives

图式22. 可见光介导的烯烃/炔烃的选择性合成

Scheme 22. Visible light-mediated selective synthesis of olefins/alkynes

图式23. N-烷基唑类化合物的合成

Scheme 23. Synthesis of N-alkyl azoles

图式24. 环戊烯-1,2,3-三酮-2-N-(烷基)腙的合成

Scheme 24. Synthesis of cyclopentene-1,2,3-trione-2-N-(alkyl)- hydrazone

图式25. 光催化醚的α-位键氨化反应

Scheme 25. Photocatalyzed α-site bonded ammonification of ethers

图式26. 苯甲酰甲酸催化的α-C—H键官能团化

Scheme 26. Benzoylformic acid-catalyzed functionalization of α-C—H bonds

图式 27. 十聚钨酸盐介导的C(sp3)—H键杂芳基化及其反应机制

Scheme 27. Decatungstate-Mediated C(sp3)—H bond Heteroarylation

图式28. EDA复合物介导的四氢呋喃α-位氨化反应

Scheme 28. EDA complex-mediated α-site amination of tetrahydrofuran

图式29. 可见光促进的环醚与亚胺碘酮的C—H氨化反应

Scheme 29. Visible light-enhanced C—H amination of cyclic ethers with iminoiodinanes

图式30. 光催化α-C—H键的缩醛化反应及其反应机理

Scheme 30. Photocatalytic α-C—H bond acetalization reaction and its reaction mechanism

图式31. 金催化杂环化合物的α-位烷氧化反应

Scheme 31. Gold-catalyzed α-site alkane oxidation of heterocyclic compounds

图式32. 光催化醚α-位烷氧化反应

Scheme 32. Photocatalytic oxidation of ether α-positions

图式33. 光催化芳基硫醚衍生物的合成及其反应机制

Scheme 33. Synthesis of photocatalytic tetrahydrofuran α-aryl thioether and its reaction mechanism

图式34. EDA复合物介导的醚的α-C—S键的构建及其反应机制

Scheme 34. Construction of α-C—S bonds of photocatalytic heterocyclic compounds and their reaction mechanisms

图式35. 光催化醚类化合物α-C—S键的构建

Scheme 35. Synthesis of photocatalytic thiol derivatives

图式36. 光催化经LMCT过程的醚类化合物α-C—S键的构建

Scheme 36. Photocatalytic construction of α-C—S bonds of ethers via LMCT process

图式37. 电催化二氮唑/三氮唑类衍生物的合成

Scheme 37. Electrocatalytic synthesis of diazole/triazole derivatives

图式38. 电催化缩醛衍生物的合成及其反应机制

Scheme 38. Synthesis of electrocatalytic acetal derivatives and their reaction mechanism

图式39. 亚磷酸辅助的磺胺类和酰胺类电化学α-四氢呋喃化反应

Scheme 39. Phosphorous acid-assisted electrochemical α-tetra- hydrofuranylation of sulfonamides and amides

图式40. 光/电协同催化异喹啉衍生物的合成

Scheme 40. Photo/electric synergistic catalytic synthesis of isoquinoline derivatives

图式41. 光/电协同催化喹啉衍生物的合成

Scheme 41. Photo/electric synergistic catalytic synthesis of quinoline derivatives

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