Photochemical Driven Diverse Transformation of α-Trifluoromethyl Olefins

doi:10.6023/A25070258

Abstract

Fluorine-containing compounds have unique physicochemical properties, which are widely used in pharmaceutical pesticide materials and other fields. Among which, easily prepared α-trifluoromethyl olefins are universal structural unit for the synthesis of various fluoro-containing molecules. Recently, the burgeoning photocatalytic technology furnish opportunities for exploring the potential to highly functionalized molecules under mild conditions, and the conversion of α-trifluoromethyl olefins under photochemical conditions has attracted much attention. In this paper, the diverse transformation of α-trifluoromethyl olefins, mainly including difunctionalization of α-trifluoromethyl olefins, defluorinative functionalization to gem-difluoroalkenes, as well as other types (non-defluorination conversion, controllable defluorination conversion and cyclization reaction), are described. Besides, some of the reaction mechanisms are also discussed.

Key words: α-trifluoromethyl olefin, photocatalysis, radical, mechanism study, defluorination

Cite this article

Tongtong Shi, Jia Li, Yifan Yin, Kai Sun. Photochemical Driven Diverse Transformation of α-Trifluoromethyl Olefins[J]. Acta Chimica Sinica, 2026, 84(1): 135-159.

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Fig. & Tab. 42

Figure 1. Trifluoromethyl-containing drugs and bioactive molecules

Figure 2. Diverse transformation of α-trifluoromethyl olefins

Figure 3. This article deals with photocatalysts

Scheme 1. Photocatalytic mediated hydroacylation of α-trifluoromethyl olefins

Scheme 2. Photocatalytic α-trifluoromethyl olefins sulfonation-hydroxylation reaction

Scheme 3. Photo-induced iron-catalyzed trifluoromethylthiolation of α-trifluoromethyl olefins

Scheme 4. Photo-induced pyridine salt-catalyzed functionalization of α-trifluoromethyl olefins

Scheme 5. Synthesis of trifluoromethylazepines by photocatalytic amination reaction

Scheme 6. Visible light-induced synthesis of trifluoromethyl alkanes and difluoroolefin compounds

Scheme 7. Photo-induced reductive alkylation reaction

Scheme 8. Photocatalytic decarboxylation or defluorination of α-trifluoromethyl olefins

Scheme 9. Photocatalytic trifluoromethylation of α-trifluoromethyl olefins

Scheme 10. Visible light-induced defluoroborylation reaction

Scheme 11. Visible light-induced synthesis of difluoroallyl ketones

Scheme 12. The visible-light-mediated direct β-C-H gem-difluoroallylation of aliphatic aldehydes and cyclic ketones

Scheme 13. Photocatalytic defluorination of α-trifluoromethyl olefins for the synthesis of difluoroallyl ketones

Scheme 14. Visible light-catalyzed synthesis of lactam-substituted gem-difluoro-alkenes from unactivated olefins

Scheme 15. Photocatalytic metal-free defluorinated arylation of α-trifluoromethyl olefins

Scheme 16. Visible light-promoted defluorinated alkylation of unsaturated hydrazones and α-trifluoromethyl olefins

Scheme 17. Photocatalytic synthesis of gem-difluoro-olefins reaction

Scheme 18. Photocatalytic defluorodichloromethylation of α-trifluoromethyl olefins

Scheme 19. Visible light-induced breakage of carbon-fluorine and carbon-nitrogen bonds for the synthesis of gem-difluoro-olefins

Scheme 20. Visible light-promoted allylation of cycloalkanols and trifluoromethyl olefins

Scheme 21. Visible light-induced defluorinated carbonylation coupling of iodoalkanes with α-trifluoromethyl olefins

Scheme 22. Visible light-induced decarboxylation or defluorination of silanes for the synthesis of gem-difluoro-olefins

Scheme 23. Photocatalytic hydrogen atom transfer defluorosilylation of α-trifluoromethyl olefins

Scheme 24. Photocatalytic gem-difluoro-allylation of iodoalkanes

Scheme 25. Photocatalytic defluorinated aryloxymethylation of α-trifluoromethyl olefins

Scheme 26. Photocatalytic gem-difluoro-allylation of tertiary amines with α-trifluoromethyl olefins

Scheme 27. Photocatalytic synthesis of difluorooxetane compounds

Scheme 28. Photocatalytic formylation reaction of α-trifluoromethyl olefins

Scheme 29. Photocatalytic alkylation reaction of α-trifluoromethyl olefins

Scheme 30. Photocatalytic defluorobenzylation of α-trifluoromethyl olefins with alkyl aromatics

Scheme 31. Visible light-catalysed difluoroallylation of silanes

Scheme 32. Visible light-driven selective difluoroalkylation of α-trifluoromethyl olefins

Scheme 33. Visible light-induced transition metal-free defluorinated silylation of α-trifluoromethyl olefins

Scheme 34. Photo-/nickel dual-catalytic defluorinated sulfonylation reaction

Scheme 35. Visible light-induced defluorinated alkylation of dihydroquinazolinones with trifluoromethyl olefins

Scheme 36. Photocatalytic synthesis of gem-difluoro-alkene compounds

Scheme 37. Photo-induced synthesis of fluoro-benzo-quinolizine-containing compounds

Scheme 38. Photocatalytic synthesis of monofluorocyclopentene

Scheme 39. Photocatalytic cascade cyclisation of α,β-unsaturated carbonyl compounds and difluoro-olefins

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