Research Progress on Direct Trifluoromethylselenylation

doi:10.6023/cjoc202206050

Abstract

The trifluoromethylselenylation reaction is another important research topic after trifluoromethylsulfanylation reaction in recent years. Because the trifluoromethylselenyl group contains two important chemical elements, fluorine and selenium, and the compounds containing trifluoromethyl selenide have important potential biological activities, more and more researchers begin to turn their attention to this new group in recent years. In this paper, according to the three reaction types of nucleophilic trifluoromethylselenylation reaction, electrophilic trifluoromethylselenylation reaction and radical trifluoromethylselenylation reaction, the research results of domestic and foreign scholars on direct trifluoromethylselenylation reaction in recent 6 years are comprehensively summarized, and some reaction mechanisms are discussed in detail. Finally, the direct trifluoromethylselenylation reaction is summarized and prospected.

Key words: trifluoromethylseleno, nucleophilic reaction, electrophilic reaction, radical reaction

Cite this article

Zhaoming Hu, Jihong Wu, Jingjing Wu, Fanhong Wu. Research Progress on Direct Trifluoromethylselenylation[J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 36-56.

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Fig. & Tab. 44

Scheme 1. Nickel-catalyzed trifluoromethylselenylation of aryl halides

Scheme 2. Catalyst-free and additive-free trifluoromethylselenation using Me4NSeCF3

Scheme 3. Binuclear nickel-catalyzed cross-coupling reaction of aryl iodide with Me4NSeCF3

Scheme 4. CaCl2 promotes dehydroxytrifluoromethylselenation of alcohols with Me4NSeCF3

Scheme 5. Markovnikov-type trifluoromethylselenylation of unactivated alkenes

Scheme 6. Copper-catalyzed radical 1,2-trifluoromethylselenation of alkenes

Scheme 7. Gold redox catalyzed trifluoromethylselenylation of aryl halides

Scheme 8. A kind of synthetic method of copper-mediated α-trifluoromethylselenyl ketone

Scheme 9. Synthesis of trifluoromethylselenopyrone derivatives

Scheme 10. Synthesis of three-component difluoroalkyl trifluoromethylselenyl compounds

Scheme 11. Efficient synthesis of α-trifluoromethylselenyl esters involved by α-diazoate

Scheme 12. Tandem synthesis of trifluoromethylselenylbenzofuran derivatives catalyzed by palladium

Scheme 13. TDAE-mediated metal-free nucleophilic trifluoromethylselenylation

Scheme 14. Iodine-mediated metal-free nucleophilic trifluoromethylselenylation

Scheme 15. Iron-mediated metal-free nucleophilic trifluoromethylselenylation

Scheme 16. Electrocatalytic activation of alkyl halides for trifluoromethylselenylation

Scheme 17. Trifluoromethylselenylation of C(sp3)—H involved by AgSeCF3

Scheme 18. Deoxytrifluoromethylselenylation of alcohols with BT-SeCF3

Scheme 19. Copper-catalyzed trifluoromethylselenylation of phenylboronic acid involved by TsSeCF3

Scheme 20. Electrophilic trifluoromethylselenylation of terminal alkynes with TsSeCF3

Scheme 21. Iron-catalyzed direct trifluoromethylselenylation of nitrogen heterocycles by TsSeCF3

Scheme 22. Trifluoromethylselenylation of benzofuran involved by TsSeCF3

Scheme 23. Palladium-catalyzed aromatic trifluoromethylselenylation based on a C—H active strategy

Scheme 24. Transition-metal-free C—H bond trifluoromethylselenylation of (hetero)arenes

Scheme 25. Synthesis of trifluoromethylselenolide without transition metal catalysis

Scheme 26. Synthesis of heterocyclic trifluoromethylselenyl compounds without transition metal catalysis

Scheme 27. Trifluoromethylselenylation of alkynyl copper(I)

Scheme 28. Electrophilic trifluoromethylselenylation of alkenes

Scheme 29. Direct α-C—H trifluoromethylselenylation of carbonyl compounds

Scheme 30. α-Trifluoromethylselenylation of carbonyl compounds

Scheme 31. Electron-rich (hetero)arene metal-free oxidative trifluoromethylselenylation

Scheme 32. Oxidative trifluoromethylselenylation of 1,3- dicarbonyl compounds

Scheme 33. Synthesis of N-acyltrifluoromethylselenoindoles

Scheme 34. Synthesis of bistrifluoromethylselenoindole derivatives by copper-mediated domino reaction

Scheme 35. Synthesis of monotrifluoromethylselenoindole derivatives by copper-mediated domino reaction

Scheme 36. Visible-light-mediated metal-free catalyzed trifluoromethylselenylation of aromatic hydrocarbons

Scheme 37. Difunctionalization of bicyclo[1,1,1]pentane and trifluoromethylselenylaryl sulfone

Scheme 38. Metal-free photoredox-catalyzed trifluoromethylselenylation of inactive olefins

Scheme 39. Photoredox catalytic decarboxylation trifluoromethylselenylation

Scheme 40. Photocatalytic ring-opening trifluoromethylselenylation of cycloalkanols

Scheme 41. Visible-light-promoted trifluoromethylselenylation of o-hydroxyarenaminones

Scheme 42. Photoredox decarboxylation trifluoromethylselenylation

Scheme 43. Photoredox heteroarene trifluoromethylselenylation

Scheme 44. Photocatalytic trifluoromethylselenylation of aryl sulfonium salts

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