Visible Light-Mediated Selective C—F Bond Cleavage of Trifluoromethyl Groups and Its Application in Synthesizing gem-Difluoro-Containing Compounds

doi:10.6023/cjoc202307004

Abstract

The unique properties of difluorinated compounds have attracted widespread attention in the fields of medicine and material sciences. The conversion of inexpensive and easily available trifluoromethyl groups into difluoro groups is of great importance in organic synthesis. However, there still exist great challenges in the selective cleavage of C—F bonds, because the dissociation energy of single C—F bond in trifluoromethyl group is much higher than that of the C—F bond in the difluoro unit of the generated product. Thus, the selective cleavage of C—F bond is difficult to control, which can easily lead to excessive defluorination. Compared with the traditional thermal reaction, the visible-light irradiated reaction provides an alternative pathway to achieve C—F cleavage more efficiently and selectively. The research progress on the selective cleavage of C—F bonds mediated by visible light in the past three years is summarized and its future perspective is prospected.

Key words: photocatalysis, free radical, C—F fracture, germinal difluoro-compound, synthesis

Cite this article

Yukun Jin, Baoyi Ren, Fushun Liang. Visible Light-Mediated Selective C—F Bond Cleavage of Trifluoromethyl Groups and Its Application in Synthesizing gem-Difluoro-Containing Compounds[J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 85-110.

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Fig. & Tab. 57

Figure 1. Drugs and liquid crystal molecules containing difluoride structures

Scheme 1. C—F bond cleavage in three types of substrates containing trifluoroalkyl groups under photocatalytic conditions

Scheme 2. Organophotoredox hydrodefluorination of trifluoromethylarenes

Scheme 3. Visible-light photoredox-catalyzed selective carboxylation of C—F bonds with CO2

Scheme 4. Radical-polar cross-coupling between p-cyanotri- fluorotoluene and arylene promoted by visible light

Scheme 5. Aromatic thiols as bifunctional catalysts for photocatalytic defluorination and alkylation

Scheme 6. Visible-light catalyzed defluoroalkylation of trifluoromethyl aromatic hydrocarbons with hydrazone

Scheme 7. Visible light-mediated defluorination and thioetherification of trifluoromethyl aromatic hydrocarbons

Scheme 8. Photocatalytic controllable defluoroalkylation and distal carbonylation of trifluoromethyl aromatics with unactivated olefins

Scheme 9. Visible-light-induced Pd-catalyzed selective defluoroarylation of trifluoromethylarenes with arylboronic acid

Scheme 10. Rare earth photocatalyst-mediated defluoroalkylation

Scheme 11. Visible light-mediated defluorination/acetalation of α-trifluoromethyl olefins

Scheme 12. Barbier-type reaction of halogenated alkanes with α-trifluoromethyl styrene activated by photoredox organozinc reagent

Scheme 13. Visible light-mediated remote region-selective functionalization of unactivated C?H bonds in amides

Scheme 14. Synthesis of CF2-substituted cyclobutene derivatives by visible light-induced one-pot synthesis

Scheme 15. Visible light-mediated continuous radical cyclization defluorination of β,γ-unsaturated hydrazone with α-trifluoro- methyl olefins

Scheme 16. Construction of difluoroolefin derivatives by photocatalysis of α-trifluoromethyl olefin and alkyl iodide by C—F bond cleavage

Scheme 17. Visible light-catalyzed difluoroallylation of silane

Scheme 18. Defluorosilanization of trifluoromethyl olefins and alkyl silanes mediated by visible light

Scheme 19. Visible light-mediated photoredox catalyzed defluo- rination of α-trifluoromethyl olefins

Scheme 20. Photocatalytic difluoroallylation of α-trifluoro- methyl olefins with tertiary amines

Scheme 21. Visible light-induced cycloaddition of cycloalkoxy to fluorinated olefins to synthesize distal fluoroalkenyl ketones

Scheme 22. Synthesis of 5-fluorodihydroindolazine derivatives by double C-F bond cleavage catalyzed by visible light

Scheme 23. Photocatalytic defluorination of N-aryl amino acids using BTP as coupling agent

Scheme 24. Photoredox-catalyzed allylation of oxalate with difluoroallylation

Scheme 25. Three-component trifluoromethylation difluoroallylation of unactivated olefins

Scheme 26. One-pot two-step synthesis of monofluorocyclopentene catalyzed by visible light

Scheme 27. Visible light-induced decarboxylation/defluorosila- nization to synthesize carboxylenes

Scheme 28. Synthesis of cardifluoroallyl aromatics catalyzed by visible light reaction of α-trifluoromethyl olefins with spatially impeded primary amines

Scheme 29. Direct difluoroallylation of alkyl aldehyde and cycloketone β-hydrocarbons under synergistic action of multiple

Scheme 30. Direct difluoroallylation of alkyl aldehyde and cycloketone β-hydrocarbons under synergistic action of multiple catalysts

Scheme 31. Defluorination and alkylation of alkyl boric acid with trifluoromethyl styrene under photoredox/Lewis base double catalysis

Scheme 32. Defluorination and boronation using N-heterocyclic carbene (NHC)-BH3 complex as boron-based precursor

Scheme 33. See photocatalytic functionalization of α-trifluoro- methyl aromatic olefins with primary, secondary and tertiary alkyl iodides

Scheme 34. Difluoroallylation of alkyl iodine catalyzed by the combination of Mn2(CO)10 and iridium-based photocatalysts

Scheme 35. Photoredox/hydrogen atom transfer co-catalysis of C—H difluoroallylation of amide, ether and alkyl aldehyde

Scheme 36. Selective defluorination of C(sp3)—H alkylation by check point of secondary amides

Scheme 37. Photoredox/Br?nsted base synergistic catalysis of amino-difluoroallylation

Scheme 38. Synthesis of carboalkyl glycosides by photocatalytic defluorination and difluoroallylation based on glycosyl radicals

Scheme 39. Catalyst-controlled divergent alkylation of α-CF3 olefins initiated by reduction quenching

Scheme 40. Ring-opening and difluoroallylation based on photocatalytic defluorination of naphthenic alcohols

Scheme 41. Visible light catalyzed series reaction of cyclopropanol with α-trifluoromethyl substituted olefins

Scheme 42. Visible light-mediated defluoroalkoxycarbonylation of trifluoromethyl olefins with alcohol oxalate derivatives

Scheme 43. Photoredox catalyzed free radical addition/defluo- roalkylation coupling reaction

Scheme 44. Photochemical defluorination reaction involved by aryl sulfonate

Scheme 45. Visible light-catalyzed defluorination and carbonylation coupling reaction of iodized alkanes with α-trifluoromethyl styrene

Scheme 46. Visible light promotes free radical [1,2]-Brook rearrangement reaction

Scheme 47. Synthesis of difluoroallyl sulfone by photocatalytic/nickel double-catalytic defluorosulfonylation

Scheme 48. Photocatalytic defluorination functionalization of polyfluoroacetamide and trifluoroacetate mediated by diarylketone

Figure 2. Photocatalytic diarylketone-mediated post-modifi- cation of polyfluoroacetamide and trifluoroacetate drug molecules

Scheme 49. Defluorination functionalization of polyfluorinated aliphatic amids and esters catalyzed by visible light redox

Scheme 50. Photocatalytic defluoroalkylation and hydrode- fluorination of trifluoromethyls using o-phosphinophenolate

Scheme 51. Photocatalytic aryl disulfide-mediated trifluoromethyl C-F bond activation

Scheme 52. Visible light-catalyzed thiophenol-mediated construction of indole skeleton with difluoroxide

Scheme 53. HFIP assisted single C-F bond activation of trifluoromethyl ketones using visible-light photoredox catalysis

Scheme 54. Single C—F bond activation of trifluoromethyl ketone controlled by visible light redox catalytic solvent

Scheme 55. Visible light induced direct C(sp3)-F alkylation of trifluoromethyl benzimidazole catalyzed by thiol

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可见光介导的三氟甲基的选择性C－F键断裂及其在偕二氟类化合物合成中的应用