Recent Progress in the Selenocyclization Reactions with Organic Selenides

doi:10.6023/cjoc202008009

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (3): 1012-1030.DOI: 10.6023/cjoc202008009 Previous Articles Next Articles

REVIEWS

有机硒参与的硒环化反应研究进展

许颖¹, 李晨¹, 孟建萍¹, 黄玉玲¹, 付纪源¹, 刘冰¹, 刘颖杰¹, 陈宁¹^,^*()

1 哈尔滨商业大学药学院哈尔滨 150076

收稿日期:2020-08-08 修回日期:2020-09-09 发布日期:2020-09-30
通讯作者: 陈宁
基金资助:
黑龙江省自然科学基金优秀青年项目(YQ2019B004); 黑龙江省自然基金面上目(H2017001); 哈尔滨商业大学青年创新人才(2016QN056); 哈尔滨商业大学青年创新人才(2019CX38); 哈尔滨商业大学青年后备人才(2019CX36); 黑龙江省自然基金联合引导(LH2020H068); 黑龙江省自然基金联合引导(LH2020H070)

Recent Progress in the Selenocyclization Reactions with Organic Selenides

Ying Xu¹, Chen Li¹, Jianping Meng¹, Yuling Huang¹, Jiyuan Fu¹, Bing Liu¹, Yingjie Liu¹, Ning Chen¹^,^*()

1 School of Pharmacy, Harbin University of Commerce, Harbin 150076

Received:2020-08-08 Revised:2020-09-09 Published:2020-09-30
Contact: Ning Chen
About author:
* Corresponding author. E-mail: liuyj691@nenu.edu.cn
Supported by:
Outstanding Youth Project of Natural Science Foundation of Heilongjiang Province(YQ2019B004); General Project of Natural Foundation of Heilongjiang Province(H2017001); Youth Innovation Talent Project of Harbin University of Commerce(2016QN056); Youth Innovation Talent Project of Harbin University of Commerce(2019CX38); Youth Reserve Talent Program of Harbin University of Commerce(2019CX36); Natural Foundation Co-pilot Project of Heilongjiang Province(LH2020H068); Natural Foundation Co-pilot Project of Heilongjiang Province(LH2020H070)

Organic selenides are a kind of important molecules, which are widely used in medicine, agricultural chemicals, organic materials and catalysis, the introduction of selenium atom into organic molecules is of great significance in the synthetic chemistry. Heterocyclic compounds are key skeletons involved in a variety of bioactive molecules, therefore, the development of new methods for the synthesis of selenium-containing heterocyclic derivatives has attracted much attentions. The recent progress in this rapidly growing area, including metal catalysis, electrochemical catalysis, visible-light catalysis, organocatalysis, and other selenocyclization types, is highlighted with an emphasis on the scope and the mechanisms of these different reactions.

Key words: organic selenide, heterocyclic compound, selenocyclization, catalysis

Cite this article

Ying Xu, Chen Li, Jianping Meng, Yuling Huang, Jiyuan Fu, Bing Liu, Yingjie Liu, Ning Chen. Recent Progress in the Selenocyclization Reactions with Organic Selenides[J]. Chinese Journal of Organic Chemistry, 2021, 41(3): 1012-1030.

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Fig. & Tab. 57

Figure 1. Selenium-containing heterocyclic bioactive molecules

Scheme 1. CuI catalyzed selenoenyne cyclization and telluroenyne cyclization

Scheme 2. Palladium catalyzed cyclization of alkynylphenol derivatives

Scheme 3. Iron(III) catalyzed cyclization of anisoles

Scheme 4. CuI catalyzed cyclization of 2-alkynylanilines

Scheme 5. Copper(II) catalyzed cyclization of high propargyl selenide

Scheme 6. Cyclization of arylpropionates and arylpropionamides catalyzed by iron salt

Scheme 7. Proposed mechanism of arylpropionates or arylpropionamides cyclization catalyzed by iron salt

Scheme 8. CuO catalyzed cyclization of 1,3-diene bromide

Scheme 9. CuO catalyzed cyclization of 1,3-diene dibromides

Scheme 10. Cyclization of functionalized nitrides catalyzed by copper

Scheme 11. Iron(III) catalyzed cyclization of arylalkynol

Scheme 12. Synthesis of triazole by copper(I) catalyzed parent selenide

Scheme 13. Copper(I) promoted formation of 1,2,3-triazoles

Scheme 14. Possible mechanism of copper(I) promoted formation of 1,2,3-triazoles

Scheme 15. Copper(I) catalyzed formation of indolizines

Scheme 16. CuI catalyzed cyclization of alkynylphenol

Scheme 17. Copper catalyzed cyclization of propargyl alcohol

Scheme 18. Copper(II) acetate-promoted formation of 1,2,3- triazoles

Scheme 19. Mechanism of copper(II) acetate-promoted formation of 1,2,3-triazoles

Scheme 20. AgNO2 catalyzed cyclization of anisole

Scheme 21. Possible way of free radical cascade cyclization

Scheme 22. Copper-catalyzed selenodifluoromethylation of alkenes

Scheme 23. Proposed mechanism of selenodifluoromethylation

Scheme 24. Copper-catalyzed sulfenoamination of β,γ-unsa- turated hydrazones with diphenyl diselenide

Scheme 25. Cyclization of dibromovinyl amine and diselenide catalyzed by Pd(OAc)2/CuI

Scheme 26. Light-induced promotion of olefins cyclization

Scheme 27. Photoinduced promotion of selenium cyclization

Scheme 28. Formation of spiro-compounds in the presence of eosyn Y under blue light

Scheme 29. Photocatalytic synthesis of benzoselenylbenzenes

Scheme 30. Photo-induced synthesis of triketene

Scheme 31. Mechanism of photo-induced synthesis of triketene

Scheme 32. Photoinduced cyclization of acetylenic cyclohexadienones and diselenides

Scheme 33. Mechanism of photoinduced cyclization of acetylenic cyclohexadienone and selenium

Scheme 34. Photocatalytic dehydrogenation and cyclization of olefins and selenium compounds

Scheme 35. Possible mechanism

Scheme 36. Electrochemical synthesis of dihydrofuran

Scheme 37. Electrochemical synthesis of oxazoline

Scheme 38. Possible mechanism electrochemical synthesis of dihydrofuran and oxazoline

Scheme 39. Electrochemical synthesis of selenide oxazoline and isoxazoline derivatives

Scheme 40. Electrochemical synthesis of coumarin and quinolinone compounds

Scheme 41. Possible mechanism electrochemical synthesis of coumarin and quinolinone compounds

Scheme 42. Electrochemical synthesis of spiro[4.5]trienones

Scheme 43. Mechanism for electrochemical synthesis of spiro- [4.5]trienones

Scheme 44. Electrochemical synthesis of selenium-containing thiazoline

Scheme 45. Mechanism for the electrochemical synthesis of thiazoline

Scheme 46. Electrophilic cyclization of alkynes and selenium

Scheme 47. Selenium cyclization of cyclopropaldehyde

Scheme 48. Electrophilic cyclization of alkyne compounds with iodine

Scheme 49. Iodine catalyzed cyclization of methanesulphonylaniline and diphenylselenide

Scheme 50. Cyclization of propargyl alcohol catalyzed by iodine

Scheme 51. Cyclization of enamine catalyzed by 1,4-diaza- bicyclo[2.2.2] octane

Scheme 52. Cyclization of alkyne compounds with selenium

Scheme 53. Cyclization of propargyl aryl ether and diaryl diselenide

Scheme 54. Proposed mechanism cyclization of propargyl aryl ether and diaryl diselenide

Scheme 55. Synthesis of triketene by cyclization

Scheme 56. Possible mechanism of synthesis of triketene

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有机硒参与的硒环化反应研究进展

Recent Progress in the Selenocyclization Reactions with Organic Selenides

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