烷基、芳基和氟烷基硒化反应的研究进展

doi:10.6023/cjoc202108001

有机化学 ›› 2022, Vol. 42 ›› Issue (2): 434-457.DOI: 10.6023/cjoc202108001 上一篇下一篇

所属专题：有机氟化学虚拟合辑

综述与进展

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)

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摘要/Abstract

有机硒化物在医药、农药、合成以及材料领域均有着十分重要的应用价值, 在抗癌、抗炎等方面有着尤为突出的作用, 因此有机含硒化合物的合成研究显得尤为重要. 有机硒化物的传统制备方法是通过硒酚或二硒醚(RSeSeR)等含硒底物与烷基或芳基化试剂反应, 近年来, 研究人员也开发了一些新型的直接烷基或芳基硒化试剂. 另一方面, 氟烷硒基化反应的研究相对较少. 开发新的烷基、芳基和氟烷基硒化反应以及新型硒化试剂具有重要研究潜力和价值. 因此主要综述了烷基、芳基和氟烷基硒化反应的最新研究进展, 并对部分反应的机理进行了论述.

关键词: 有机硒化物, 硒化反应, 氟烷基硒化反应

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

引用此文

李珊, 曹原, 蒋绿齐. 烷基、芳基和氟烷基硒化反应的研究进展[J]. 有机化学, 2022, 42(2): 434-457.

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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图/表 58

图1. 具有生物活性的有机硒化合物

Figure 1. Organoselenium compounds with bioactive activities

图式1. 叶立德结构硒化试剂参与的硒化反应

Scheme 1. Selenylation with selenated yelid reagent

图式2. 苯硒基酸酐参与的硒化反应

Scheme 2. Selenylation with phenylselenyl anhydride

图式3. 钯催化下苯甲酰胺衍生物与二硒醚的硒化反应

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

图式4. 吲哚与二硒醚的硒化反应

Scheme 4. Selenylation with indols and RSeSeR

图式5. 咪唑并[2,1-b]噻唑与二硒醚的硒化反应及机理

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

图式6. 二硒醚参与的脱羧硒化反应及其应用

Scheme 6. Decarboxylative selenation with RSeSeR and its application

图式7. β,γ-不饱和腙和肟的自由基环化硒化反应及机理

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

图式8. 光催化条件下二硒醚参与的硒化反应及机理

Scheme 8. Photocatalytic selenylation of RSeSeR and its mechanism

图式9. 光照射条件下碘催化的烯烃、二硒醚类和醇的硒化反应

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

图式10. 茂钛全氟丁基磺酸盐/锌粉体系催化二芳基二硒醚与溴代烷反应制备不对称单硒醚

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

图式11. [{Ti(salophen)H2O}2O][OSO2C4F9]2催化的硒化反应及机理

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

图式12. 二硒醚参与的咪唑的硒化反应

Scheme 12. Selenation of imidazoles with RSeSeR

图式13. 芳基(N3-替加氟烷基)硒醚衍生物的合成

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

图式14. 电催化条件下二硒醚参与的5尿嘧啶和喹诺酮的硒化反应

Scheme 14. Electrochemical selenylation of uracils and quinolones with RSeSeR

图式15. 电催化条件下多组分反应合成4-硒基吡唑

Scheme 15. Electrochemical multicomponent synthesis of 4- selanylpyrazoles

图式16. 铜催化的硒粉和芳基碘代物参与的环氧乙烷的开环反应

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

图式17. 硒粉参与的吲哚硒化反应及机理

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

图式18. 铜催化下硒粉参与的硒化反应

Scheme 18. Cooper-catalyzed selenylation with Se powder

图式19. 镍催化下硒粉参与的硒化反应

Scheme 19. Nickel-catalyzed selenylation with Se powder

图式20. 苯并噻唑和咪唑并[1,2-α]吡啶的硒化反应及其机理

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

图式21. DCP促进的硒化反应及其机理

Scheme 21. DCP-promoted selenylation and proposed mechanism

图式22. 硒粉参与的自由基环化硒化反应及其机理

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

图式23. RSeCl参与的硒化反应

Scheme 23. Selenylation with RSeCl

图式24. N-硒苯基邻苯二甲酰亚胺参与的硒化反应及其机理

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

图式25. N-苯硒基邻苯甲酰磺酰亚胺的合成及其作为硒化试剂的应用

Scheme 25. Synthesis of NPSSac and its application in selenylation

图式26. 路易斯碱催化的硒化内酯化反应

Scheme 26. Lewis base catalyzed selenolactonization

图式27. NPSS及NPASS对烯醇进行高对映选择性环化硒化反应及机理

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

图式28. NPSP参与的硒化反应

Scheme 28. Selenylation with NPSP

图式29. TPSCA的合成与应用

Scheme 29. Synthesis and application of TPSCA

图式30. 硒代Bunte盐的合成与应用

Scheme 30. Synthesis and application of seleno Bunte salts

图式31. RSeO2Na参与的硒化反应及机理

Scheme 31. Selenylation with RSeO2Na and proposed mechanism

图式32. 苯硒酚与氯二氟甲基乙酸钠的二氟甲基化反应

Scheme 32. Difluoromethylation of phenylselenol with sodium chlorodifluoroacetate

图式33. 苯硒酚与(二氟甲基)三苯基溴化膦的二氟甲硒基化反应

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

图式34. 二硒醚参与的二氟甲基化反应

Scheme 34. Difluoromethylation of RSeSeR

图式35. 二硒醚参与的三氟甲基化反应

Scheme 35. Trifluoromethylation of RSeSeR

图式36. 二硒醚参与的氟烷基化反应

Scheme 36. Fluoromethylation with RSeSeR

图式37. 由α,α-二氟二苯甲酰甲烷合成二氟甲硒基取代芳烃

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

图式38. 18F标记的二硒醚的三氟甲基化反应

Scheme 38. 18F-trifluoromethylation of RSeSeR

图式39. TMSCF3和二硒醚的三氟甲基化反应

Scheme 39. Trifluoromethylation of RSeSeR using TMSCF3

图式40. [Cu(bpy(SeCF3))]2参与的三氟甲硒基化反应

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

图式41. [(phen)Cu(SeCF3)]2参与的三氟甲硒基化反应

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

图式42. [(phen)Cu(SeCF3)]2参与的三氟甲硒基化反应

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

图式43. 硼吖嗪衍生物参与的三氟甲硒基化反应

Scheme 43. Trifluoromethyselenylation with boracazine derivatives

图式44. PDFA和硒粉参与的三氟甲硒基化反应及机理

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

图式45. 原位生成ClSeRf作为亲电氟烷硒基化试剂

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

图式46. 原位生成ClSeRf与炔铜化合物的氟烷硒基化反应

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

图式47. 钯催化的芳基碘代物的三氟甲硒基化反应

Scheme 47. Pd-catalyzed trifluoromethyselenylation of aryl iodides

图式48. 钯催化的芳基碘代物的三氟甲硒基化反应

Scheme 48. Pd-catalyzed trifluoromethyselenylation of aryl iodides

图式49. 末端炔烃、芳基硼酸和芳基联硼酸频那醇酯参与的三氟甲硒基化反应

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

图式50. 芳基卤代物和(Me4N)SeCF3的三氟甲硒基化反应

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

图式51. 富电子(杂)芳环化合物和(Me4N)SeCF3的三氟甲硒基化反应

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

图式52. (Me4N)SeCF3参与的脱羧三氟甲硒基化反应

Scheme 52. Decarboxylative trifluoromethylselenolation with (Me4N)SeCF3

图式53. Cu催化的AgSeCF3参与的C(sp3)—H的三氟甲硒基化反应

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

图式54. TsSeRf参与的苯硼酸的三氟甲硒基化反应

Scheme 54. Trifluoromethyselenylation of boronic acids with TsSeRf

图式55. TsSeCF3参与的氮杂环化合物的三氟甲硒基化反应

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

图式56. TsSeCF2H参与的芳胺类化合物的二氟甲硒基化反应

Scheme 56. Difluoromethyselenylation of arylamines with TsSeCF2H

图式57. BT-SeCF3参与的醇类化合物的三氟甲硒基化反应

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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