Recent Progress on Alkyl-, Aryl- and Fluoroalkyl-selenylation Reactions

doi:10.6023/cjoc202108001

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (2): 434-457.DOI: 10.6023/cjoc202108001 Previous Articles Next Articles

Special Issue: 有机氟化学虚拟合辑

REVIEWS

烷基、芳基和氟烷基硒化反应的研究进展

李珊^a^,^b, 曹原^a, 蒋绿齐^a^,^*()

a 南京理工大学化工学院南京 210094
b 沙洲职业工学院江苏张家港 215600

收稿日期:2021-08-02 修回日期:2021-09-23 发布日期:2022-02-24
通讯作者: 蒋绿齐
作者简介:
^† 共同第一作者
基金资助:
国家自然科学基金(21776138); 国家自然科学基金(22078161); 国家自然科学基金(22108124); 中央高校基本科研业务费专项资金(30918011314); 江苏省自然科学基金(BK20141394); 江苏省青蓝计划和六大高峰人才(22108124)

Recent Progress on Alkyl-, Aryl- and Fluoroalkyl-selenylation Reactions

Shan Li^a^,^b, Yuan Cao^a, Lüqi Jiang^a()

a Chemical Engineering College, Nanjing University of Science and Technology, Nanjing 210094
b Shazhou Professional Institute of Technology, Zhangjiagang, Jiangsu 215600

Received:2021-08-02 Revised:2021-09-23 Published:2022-02-24
Contact: Lüqi Jiang
About author:
^† These authors contributed equally to this work.
Supported by:
National Natural Science Foundation of China(21776138); National Natural Science Foundation of China(22078161); National Natural Science Foundation of China(22108124); Fundamental Research Funds for the Central Universities(30918011314); Natural Science Foundation of Jiangsu Province(BK20141394); Qing Lan and Six Talent Peaks in Jiangsu Province(22108124)

Organoselenium compounds have great application value in the fields of medicine, pesticide, synthesis and materials, and play a particularly prominent role in anti-cancer and anti-inflammatory. Therefore, the synthesis of organoselenium compounds is particularly important in organic synthesis. The traditional methods of synthesizing organoselenium compounds were using selenol or selenium ether react with alkylation or arylation reagents. Various direct alkyl- and aryl-selenylation reagents were also developed in recent years. Moreover, there are few studies on fluoroalkylselenylation. Thus, it is still highly desirable to develop new methods for alkyl-, aryl- and fluoro-alkylselenylation as well as new types of corresponding selenylation reagents. The recent development of alkyl-, aryl- and fluoro-alkylselenylation is summarized, and part of their mechanisms are also discussed.

Key words: organoselenium compounds, selenylation, fluoroalkylselenylation

Cite this article

Shan Li, Yuan Cao, Lüqi Jiang. Recent Progress on Alkyl-, Aryl- and Fluoroalkyl-selenylation Reactions[J]. Chinese Journal of Organic Chemistry, 2022, 42(2): 434-457.

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Fig. & Tab. 58

Figure 1. Organoselenium compounds with bioactive activities

Scheme 1. Selenylation with selenated yelid reagent

Scheme 2. Selenylation with phenylselenyl anhydride

Scheme 3. Pd-catalyzed selenylation of benzamide derivatives with RSeSeR

Scheme 4. Selenylation with indols and RSeSeR

Scheme 5. Selenylation reaction and mechanism of imidazo [2,1-b]thiazole and RSeSeR

Scheme 6. Decarboxylative selenation with RSeSeR and its application

Scheme 7. Radical cyclization selenylation of β,γ-unsaturated hydrazones and oximes and its mechnism

Scheme 8. Photocatalytic selenylation of RSeSeR and its mechanism

Scheme 9. Visible light-promoted, iodine-catalyzed selenoalkoxylation of olefins with diselenides and alcohols

Scheme 10. Preparation of unsymmetrical selenides by reaction of diaryl diselenides with bromoalkanes catalyzed by tianocene perfluorobutanesulfonate/Zn system

Scheme 11. [{Ti(salophen)H2O}2O][OSO2C4F9]2-catalyzed selenylation and its mechanism

Scheme 12. Selenation of imidazoles with RSeSeR

Scheme 13. Synthesis of aryl (N3-tegafluoroalkyl)seleno-ethers derivatives

Scheme 14. Electrochemical selenylation of uracils and quinolones with RSeSeR

Scheme 15. Electrochemical multicomponent synthesis of 4- selanylpyrazoles

Scheme 16. Copper-catalyzed oxirane-opening reaction with aryl iodides and Se powder

Scheme 17. Selenylation of indoles with Se powder and its mechanism

Scheme 18. Cooper-catalyzed selenylation with Se powder

Scheme 19. Nickel-catalyzed selenylation with Se powder

Scheme 20. Selenylation of benzothiazole and imidazo[1,2-α]pyridines and proposed mechanism

Scheme 21. DCP-promoted selenylation and proposed mechanism

Scheme 22. Radical cyclization selenylation with Se powder and proposed mechanism

Scheme 23. Selenylation with RSeCl

Scheme 24. Selenylation with N-(phenylseleno)phthalimide and proposed mechanism

Scheme 25. Synthesis of NPSSac and its application in selenylation

Scheme 26. Lewis base catalyzed selenolactonization

Scheme 27. High enantioselective cyclization selenylation of enols by NPSS and NPASS and proposed mechanism

Scheme 28. Selenylation with NPSP

Scheme 29. Synthesis and application of TPSCA

Scheme 30. Synthesis and application of seleno Bunte salts

Scheme 31. Selenylation with RSeO2Na and proposed mechanism

Scheme 32. Difluoromethylation of phenylselenol with sodium chlorodifluoroacetate

Scheme 33. Difluoromethylation of phenylselenol using (difluoromethyl)triphenylphosphonium bromide

Scheme 34. Difluoromethylation of RSeSeR

Scheme 35. Trifluoromethylation of RSeSeR

Scheme 36. Fluoromethylation with RSeSeR

Scheme 37. Synthesis of difluoromethylselenylated arenes from α,α-difluorodibenzoylmethane

Scheme 38. 18F-trifluoromethylation of RSeSeR

Scheme 39. Trifluoromethylation of RSeSeR using TMSCF3

Scheme 40. Trifluoromethyselenylation with [Cu(bpy(SeCF3))]2

Scheme 41. Trifluoromethyselenylation with [(phen)Cu- (SeCF3)]2

Scheme 42. Trifluoromethyselenylation with [(phen)Cu(Se- CF3)]2

Scheme 43. Trifluoromethyselenylation with boracazine derivatives

Scheme 44. Trifluoromethyselenylation with Se powder/PDFA and the proposed mechanism

Scheme 45. ClSeRf formed in situ as electrophilic fluoroalkyl selenidation reagent

Scheme 46. Fluoroalkylselenolations of alkynyl copper(I) compounds using in suit generated ClSeRf

Scheme 47. Pd-catalyzed trifluoromethyselenylation of aryl iodides

Scheme 48. Pd-catalyzed trifluoromethyselenylation of aryl iodides

Scheme 49. Trifluoromethyselenylation with terminal alkynes, aryl boric acid and aryl borate phenyl ester

Scheme 50. Trifluoromethyselenylation of aryl halides with (Me4N)SeCF3

Scheme 51. Trifluoromethylselenolation of electron-rich (hetero)arenes with (Me4N)SeCF3

Scheme 52. Decarboxylative trifluoromethylselenolation with (Me4N)SeCF3

Scheme 53. Copper-catalyzed C(sp3)—H trifluoromethylselenation with AgSeCF3

Scheme 54. Trifluoromethyselenylation of boronic acids with TsSeRf

Scheme 55. Trifluoromethyselenylation of nitrogen-containing heterocyclic compounds with TsSeCF3

Scheme 56. Difluoromethyselenylation of arylamines with TsSeCF2H

Scheme 57. Trifluoromethyselenylationof of alcohols with BT-SeCF3

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烷基、芳基和氟烷基硒化反应的研究进展

Recent Progress on Alkyl-, Aryl- and Fluoroalkyl-selenylation Reactions

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