Study on the Application of Photoelectric Technology in the Synthesis of Selenium-Containing Heterocycles

doi:10.6023/cjoc202109046

Abstract

Selenium-containing heterocycles are a kind of important organic molecules, which are widely used in medicine, agrochemicals, organic materials and other fields. Therefore, the introduction of selenium atom into organic molecules is of great significance in synthetic chemistry. Visible light and electrochemical technology is one of the green and sustainable synthesis methods, which has opened up broad application prospects in the fields of bifunctionalization and cyclization of unsaturated bonds and direct functionalization of C—H bonds. In recent years, the development of novel selenium cyclization reaction using photoelectric technology to drive unsaturated bonds and direct selenization reaction of C—H bonds has attracted much attention. Therefore, this paper describes the electrochemical-driven and visible-light-induced synthesis reactions of selenium-containing heterocycles, and discusses the applicable scope and mechanism of some reactions.

Key words: organic selenium compounds, selenium cyclization, alkenes and alkynes, visible light, electrochemistry

Cite this article

Xin Wang, Yan Zhang, Kai Sun, Jianping Meng, Bing Zhang. Study on the Application of Photoelectric Technology in the Synthesis of Selenium-Containing Heterocycles[J]. Chinese Journal of Organic Chemistry, 2021, 41(12): 4588-4609.

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Fig. & Tab. 61

Figure 1. Selenium-containing heterocyclic bioactive molecules

Scheme 1. Electrochemical synthesis of tetrahydrofurans

Scheme 2. Possible mechanism electrochemical synthesis of dihydrofurans and oxazolines

Scheme 3. Electrochemical synthesis of selenide oxazolines and isoxazoline derivatives

Scheme 4. Possible mechanism of electrochemical synthesis of selenized oxazolines and isoxazoline derivatives

Scheme 5. Electrochemical synthesis of coumarins and quinolinone compounds

Scheme 6. Possible mechanism electrochemical synthesis of coumarins and quinolinone compounds

Scheme 7. Electrochemical synthesis of dihydrofurans and oxazolines

Scheme 8. Electrochemical synthesis of indole derivatives

Scheme 9. Possible mechanism of electrochemical synthesis of indole derivatives

Scheme 10. Electrochemical synthesis of spiro[4.5]trienones

Scheme 11. Mechanism for electrochemical synthesis of spiro [4.5] trienones

Scheme 12. Electrochemical synthesis of selenium-containing dihydrofurans

Scheme 13. Electrochemical synthesis of quinone compounds

Scheme 14. Electrochemical synthesis of iminoisobenzofurans

Scheme 15. Electrochemical synthesis of helix [4.5] trienones

Scheme 16. Electrochemical synthesis of 5-selenide uracils

Scheme 17. Electrochemical synthesis of 5-organoselenyluracils

Scheme 18. Electrochemical oxidation of imidazopyridines or electron-rich aromatic hydrocarbons

Scheme 19. Electrochemical synthesis of selenized isoquinolones

Scheme 20. Mechanism of isoquinolones

Scheme 21. Light-induced synthesis of 2,4-diselenoquinolines

Scheme 22. Light-induced promotion of olefins cyclization

Scheme 23. Photo-induced synthesis of triketenes

Scheme 24. Mechanism of photo-induced synthesis of triketenes

Scheme 25. Photoinduction promote the synthesis of 3-phenylselenyl substituted nitrospirone[4.5]trienones

Scheme 26. Light induction promotes the synthesis of 3-selenoindoles

Scheme 27. Possible mechanism of light-induced promoting synthesis of 3-selenoindoles

Scheme 28. Photoinduced cyclization of acetylenic cyclohexadienones and diselenides

Scheme 29. Mechanism of photoinduced cyclization of acetylenic cyclohexadienones and seleniums

Scheme 30. Visible-light catalyzed intramolecular dearomatic carbon helical cyclization

Scheme 31. Visible-light catalyzed synthesis of selenized cyclopentanone derivatives

Scheme 32. Photocatalytic dehydrogenation cyclization of olefins and disselenium ethers

Scheme 33. Possible mechanism

Scheme 34. Visible light promotes the synthesis of substituted pyrrolidines containing chalcogen elements

Scheme 35. Mechanism of synthesis of substituted pyrrolidines

Scheme 36. Visible light catalyzed synthesis of 4-seleno 3,3- difluoro-γ-lactam

Scheme 37. Visible-light catalyzed synthesis of 4-seleno 3,3- difluoro-γ-lactam mechanism

Scheme 38. Visible light catalyzed synthesis of 2,3-diselenoyl- quinoxalines

Scheme39. Visible light catalyzed synthesis of 3-selenospirene compounds

Scheme 40. Visible light promoted three-component cascade reaction

Scheme 41. Visible light-promoted three-component cascade reaction mechanism

Scheme 42. Visible light promotes the selenization and cyclization of alkenyl ethers

Scheme 43. Visible light promotes the selenization and cyclization mechanism of alkenyl ethers

Scheme 44. Light-induced promotes direct selenization of aryls and heteroaryl amines

Scheme 45. Light-induced copper-catalyzed seleno-arylation products

Scheme 46. Light-induced direct C—H bond selenization of 5-methoxyindole and diphenyl diselenides

Scheme 47. Light-induced synthesis of denitrification and selenization products

Scheme 48. Light-induced synthesis of coumarins containing selenium

Scheme 49. Mechanism of light-induced synthesis of coumarins containing selenium

Scheme 50. Light-induced synthesis of trifluoromethyl selenide aromatic hydrocarbons

Scheme 51. Possible mechanism of light-induced synthesis of trifluoromethyl selenide aromatic hydrocarbons

Scheme 52. Light-induced direct selenization of aromatics and heteroaromatics

Scheme 53. Light-induced preparation of selenoindoles, imidazoles and aromatics

Scheme 54. Light-induced synthesis of trifluoromethyl selenide arenes

Scheme 55. Visible light-induced synthesis of 3-arylselenoindoles

Scheme 56. Visible light-induced indole synthesis mechanism of 3-arylselenoindoles

Scheme 57. Visible light promotes the synthesis of 3-selenoindoles

Scheme 58. Visible light promotes the reaction mechanism of 3-selenoindoles

Scheme 59. Electrochemical synthesis of 3-selenoindoles and unsymmetrical diarylselenides

Scheme 60. Visible light-induced synthesis of asymmetric heteroaryl selenides

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