光电技术在含硒杂环合成中的应用研究

doi:10.6023/cjoc202109046

摘要/Abstract

含硒杂环是一类重要的有机分子, 在医药、农用化学品、有机材料等领域有着广泛的应用. 因此, 有机分子中引入硒原子在合成化学中具有重要意义. 可见光和电化学技术是较为绿色、可持续的合成方法之一, 在不饱和键的双官能化、环化以及C—H键的直接官能化等领域开辟了广阔的应用前景. 近年来, 发展新颖的利用光电技术驱动不饱和键的硒环化反应和C—H键的直接硒化反应备受关注. 分别描述了近年快速发展的电化学驱动、可见光诱导含硒杂环的合成反应, 并对部分反应的适用范围和机理进行了讨论.

关键词: 有机硒化合物, 硒环化, 烯炔烃, 可见光, 电化学

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

引用此文

王薪, 张艳, 孙凯, 孟建萍, 张冰. 光电技术在含硒杂环合成中的应用研究[J]. 有机化学, 2021, 41(12): 4588-4609.

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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图/表 61

图1. 含硒的杂环生物活性分子

Figure 1. Selenium-containing heterocyclic bioactive molecules

图式1. 电化学合成四氢呋喃类化合物

Scheme 1. Electrochemical synthesis of tetrahydrofurans

图式2. 电化学合成二氢呋喃和噁唑啉的可能机理

Scheme 2. Possible mechanism electrochemical synthesis of dihydrofurans and oxazolines

图式3. 电化学合成硒化噁唑啉和异噁唑啉衍生物

Scheme 3. Electrochemical synthesis of selenide oxazolines and isoxazoline derivatives

图式4. 电化学合成硒化噁唑啉和异噁唑啉衍生物的可能机理

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

图式5. 电化学合成香豆素和喹啉酮类化合物

Scheme 5. Electrochemical synthesis of coumarins and quinolinone compounds

图式6. 电化学合成香豆素和喹啉酮类化合物的可能机理

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

图式7. 电化学合成二氢呋喃和噁唑啉

Scheme 7. Electrochemical synthesis of dihydrofurans and oxazolines

图式8. 电化学合成吲哚衍生物

Scheme 8. Electrochemical synthesis of indole derivatives

图式9. 电化学合成吲哚衍生物的可能机理

Scheme 9. Possible mechanism of electrochemical synthesis of indole derivatives

图式10. 电化学合成螺环[4.5]三烯酮

Scheme 10. Electrochemical synthesis of spiro[4.5]trienones

图式11. 螺[4.5]三烯酮的电化学合成机理

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

图式12. 电化学合成含硒二氢呋喃

Scheme 12. Electrochemical synthesis of selenium-containing dihydrofurans

图式13. 电化学合成醌类化合物

Scheme 13. Electrochemical synthesis of quinone compounds

图式14. 电化学合成亚氨基异苯并呋喃

Scheme 14. Electrochemical synthesis of iminoisobenzofurans

图式15. 电化学合成螺旋[4.5]三烯酮

Scheme 15. Electrochemical synthesis of helix [4.5] trienones

图式16. 电化学合成5-硒化尿嘧啶

Scheme 16. Electrochemical synthesis of 5-selenide uracils

图式17. 电化学合成5-有机硒基酰尿嘧啶

Scheme 17. Electrochemical synthesis of 5-organoselenyluracils

图式18. 咪唑吡啶或富电子芳烃的电化学氧化

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

图式19. 电化学合成硒化异喹诺酮类

Scheme 19. Electrochemical synthesis of selenized isoquinolones

图式20. 异喹诺酮的机理

Scheme 20. Mechanism of isoquinolones

图式21. 光诱导合成2,4-二硒代喹啉

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

图式22. 光诱导促进烯烃环化

Scheme 22. Light-induced promotion of olefins cyclization

图式23. 光诱导促进合成三烯酮

Scheme 23. Photo-induced synthesis of triketenes

图式24. 光诱导促进合成三烯酮的机理

Scheme 24. Mechanism of photo-induced synthesis of triketenes

图式25. 光诱导促进合成3-苯硒基取代氮螺[4.5]三烯酮

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

图式26. 光诱导促进合成3-硒基吲哚

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

图式27. 光诱导促进合成3-硒基吲哚的可能机理

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

图式28. 光诱导的炔系环己二烯酮与二硒醚环化

Scheme 28. Photoinduced cyclization of acetylenic cyclohexadienones and diselenides

图式29. 光诱导的炔系环己二烯酮与硒环化的机理

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

图式30. 可见光催化的分子内脱芳碳螺旋环化

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

图式31. 可见光催化合成硒化环戊酮衍生物

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

图式32. 光催化烯烃与二硒醚的脱氢环化

Scheme 32. Photocatalytic dehydrogenation cyclization of olefins and disselenium ethers

图式33. 可能的机理

Scheme 33. Possible mechanism

图式34. 可见光出促进合成含硫属元素的取代吡咯烷

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

图式35. 合成取代吡咯烷的机理

Scheme 35. Mechanism of synthesis of substituted pyrrolidines

图式36. 可见光催化合成4-硒代3,3-二氟-γ-内酰胺

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

图式37. 可见光催化合成4-硒代3,3-二氟-γ-内酰胺的机理

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

图式38. 可见光催化合成2,3-双硒酰喹噁唑啉

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

图式39. 可见光催化合成3-硒代螺烯类化合物

Scheme39. Visible light catalyzed synthesis of 3-selenospirene compounds

图式40. 可见光促进的三组分串联反应

Scheme 40. Visible light promoted three-component cascade reaction

图式41. 可见光促进的三组分串联反应机理

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

图式42. 可见光促进烯醚的硒化环化

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

图式43. 可见光促进烯醚的硒化环化机理

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

图式44. 光诱导促进芳基和杂芳基胺直接硒化

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

图式45. 光诱导铜催化的硒代芳基化产物

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

图式46. 光诱导5-甲氧基吲哚与二苯二硒化物直接C—H键硒化

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

图式47. 光诱导合成脱氮硒化产物

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

图式48. 光诱导合成含硒的香豆素

Scheme 48. Light-induced synthesis of coumarins containing selenium

图式49. 光诱导合成含硒香豆素的机理

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

图式50. 光诱导合成三氟甲基硒化芳烃

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

图式51. 光诱导合成三氟甲基硒化芳烃的可能机理

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

图式52. 光诱导芳烃和杂芳烃直接硒化反应

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

图式53. 光诱导制备硒代吲哚、咪唑和芳烃

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

图式54. 光诱导合成三氟甲基硒化芳烃

Scheme 54. Light-induced synthesis of trifluoromethyl selenide arenes

图式55. 可见光诱导3-芳基硒代吲哚的合成

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

图式56. 可见光诱导吲哚合成3-芳基硒基吲哚的机理

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

图式57. 可见光促进3-硒基吲哚的合成

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

图式58. 可见光促进3-硒基吲哚合成的反应机理

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

图式59. 电化学合成3-硒代吲哚和不对称二芳基硒化物

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

图式60. 可见光诱导不对称杂芳基硒化物的合成

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

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