Progress of α-Position Functionalization of Ethers under Photo/Electrocatalysis

doi:10.6023/cjoc202305011

Abstract

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

Cite this article

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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Fig. & Tab. 41

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

Scheme 2. Photocatalytic alkylation of tetrahydrofuran

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

Scheme 4. Synthesis of coumarin derivatives

Scheme 5. Photochemical nickel-catalyzed C—H arylation

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

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

Scheme 8. Synthesis of alkenone derivatives

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

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

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

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

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

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

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

Scheme 16. H2O2-mediated hydroalkylation of terminal alkynes

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

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

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

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

Scheme 21. Photocatalytic synthesis of α-alkynyl ether derivatives

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

Scheme 23. Synthesis of N-alkyl azoles

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

Scheme 25. Photocatalyzed α-site bonded ammonification of ethers

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

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

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

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

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

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

Scheme 32. Photocatalytic oxidation of ether α-positions

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

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

Scheme 35. Synthesis of photocatalytic thiol derivatives

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

Scheme 37. Electrocatalytic synthesis of diazole/triazole derivatives

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

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

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

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

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