Construction of Fluoro-containing Heterocycles Mediated by Free Radicals

doi:10.6023/cjoc202109033

Abstract

Fluoro-containing heterocyclics play an important role in many fields, such as organic chemistry, pharmaceutical chemistry and material science due to their excellent physical and chemical properties. However, there are few natural fluoro-containing heterocyclics in nature, so it is particularly important to develop efficient synthesis methods of fluoro- containing heterocyclics. With the rapid development of transition metal catalyzed, photocatalyzed and electrocatalyzed radical reactions, radical chemistry has made a breakthrough in the field of synthesis and stimulated the interest of organic chemists in constructing fluoro-containing heterocyclics by using radical chemistry. In this paper, monofluoroalkylation, difluoroalkylation, trifluoromethylation, trifluoroalkoxy/sulfur/selenylation, perfluoroalkylation of unsaturated hydrocarbons and direct C—H fluoroalkylation of heterocycles are classified, and the construction of fluorine-containing side chain heterocycles mediated by free radicals is discussed from the aspects of transition metal catalysis, photocatalysis and electrocatalysis.

Key words: radical, fluorinated heterocycle, metal catalysis, photocatalytic, electrocatalysis

Cite this article

Ning Chen, Jia Lei, Zhichuan Wang, Yingjie Liu, Kai Sun, Shi Tang. Construction of Fluoro-containing Heterocycles Mediated by Free Radicals[J]. Chinese Journal of Organic Chemistry, 2022, 42(4): 1061-1084.

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Fig. & Tab. 80

Scheme 1. Monofluoromethylation of N-arylacrylamides

Scheme 2. Synthesis and mechanism of CH2F-containing coumarins

Scheme 3. Pd-catalyzed intramolecular aryldifluoromethylation of alkenes

Scheme 4. Difluoromethylation of ICF2CO2Et with 1,6-enyne

Scheme 5. Difluoromethylation of 3-propargylamide-substituted and 2-propargylamide-substituted indoles and α-bromodifluoroacetamides

Scheme 6. Aminodifluoroalkylation of alkynes and α-bromodi- fluoroacetamides

Scheme 7. Mechanism for aminodifluoroalkylation of alkynes and α-bromodifluoroacetamides

Scheme 8. Synthesis of difluorinated pyrrolizidines and indolizidines

Scheme 9. Difluoromethylation of ICF2COOEt with N-pro- pargylamide

Scheme 10. Oxydifluoroalkylation of unsaturated carboxylic acids

Scheme 11. Cobalt-catalyzed difluoroalkylation of alkyne-tethered cyclohexadienones

Scheme 12. Synthesis of difluoroalkylated benzofuran, benzothiophene, and indole derivatives

Scheme 13. Cu-catalyzed selenodifluoromethylation of alkenes

Scheme 14. Mechanism for Cu-catalyzed selenodifluoromethylation of alkenes

Scheme 15. Synthesis of difluoroalkylated 1-indenones

Scheme 16. Copper-catalyzed bromodifluoroacetylative cyclization of enynes

Scheme 17. Radical (phenylsulfonyl)difluoromethylation of isocyanides

Scheme 18. Base promoted difluoromethylation of 1,6-enynes

Scheme 19. Aryldifluoroacetylation of phenyl alkynoates with BrCF2CO2Et

Scheme 20. Aminodifluoroalkylation of alkenes with bromodifluoroacetamides

Scheme 21. Visible-light-mediated difluoroalkylation-amidation of free anilines

Scheme 22. Synthesis of gem-difluorinated spiro-γ-lactam oxindoles

Scheme 23. Sequential difluoromethylative dearomatization, hydroxylation, and substitution of indole derivatives

Scheme 24. Synthesis of difluoroacetylated chroman-4-ones

Scheme 25. Mechanism for synthesis of difluoroacetylated chroman-4-ones

Scheme 26. Synthesis of 3-CF2-containing coumarins

Scheme 27. Synthesis of difluoromethylated 2-oxindoles and quinoline-2,4-diones

Scheme 28. Mechanism for synthesis of difluoromethylated 2-oxindoles

Scheme 29. Difluoromethylarylation reaction of CF2HSO2NHNHBoc with alkynes

Scheme 30. Mechanism for difluoromethylarylation reaction of CF2HSO2NHNHBoc with alkynes

Scheme 31. Synthesis of CF2H-containing lactones

Scheme 32. Electrocatalytic fluoroalkylation/cyclization/indole oxidative cleavage reaction

Scheme 33. Mechanism of electrocatalytic fluoroalkylation/cyclization/indole oxidative cleavage reaction

Scheme 34. Synthesis of trifluoroethyl isoquinolines

Scheme 35. Synthesis of trifluoromethyl-containing 1'H-spiro-[azirine-2,4'-quinolin]-2'(3'H)-ones

Scheme 36. Synthesis of trifluoromethyl-containing 1,8-naph- thyridines

Scheme 37. Synthesis of 2,2,2-trifluoroethyl oxazoles, oxazolines and furans

Scheme 38. One-pot synthesis of fully-substituted trifluoroethyl pyrroles

Scheme 39. Mechanism for one-pot synthesis of fully-substituted trifluoromethyl pyrroles

Scheme 40. Reaction of α-benzylated tosylmethyl isocyanide derivatives with Togni reagent

Scheme 41. Photoinduced radical trifluoromethyliodation of benzene-tethered 1,7-enyne

Scheme 42. Photoinduced trifluoromethylation of 2-ethynylben- zenesulfonamide with Togni’s reagent

Scheme 43. Synthesis of CF3-containing heterocyclic compounds

Scheme 44. Bromo-trifluoromethylation of 1,7-enynes

Scheme 45. Trifluoromethylation of N-benzamides

Scheme 46. Synthesis of trifluoromethylated dibenz[b,e]azepine

Scheme 47. Trifluoromethylation/cyclization of 1,7-enynes

Scheme 48. Mechanism for trifluoromethylation/cyclization of 1,7-enynes

Scheme 49. Photocatalytic nitrene transfer reactions

Scheme 50. Synthesis of chlorotrifluoromethylated pyrrolidines

Scheme 51. Electrochemical trifluoromethylation/cyclization of N-arylacrylamides

Scheme 52. Mn-Mediated electrochemical trifluoromethylation of azaheterocycles

Scheme 53. Intramolecular trifluoromethylation of N-tethered alken-6-ols

Scheme 54. Mechanism for intramolecular trifluoromethylation of N-tethered alken-6-ols

Scheme 55. Trifluoromethylation of cyclic N-sulfonylimines

Scheme 56. Electrochemical tandem fluoroalkylation/cycli- zation of vinyl azides

Scheme 57. Synthesis of CF3- and SCF3-containing indolo[2,1-a]isoquinolin-6(5H)-ones

Scheme 58. Trifluoromethoxylation of (hetero)arenes

Scheme 59. Synthesis of SCF3-containing benzoxazines and oxazolines

Scheme 60. Trifluoromethylthiolation of N-(o-cyanobiaryl)acrylamides

Scheme 61. Synthesis of trifluoromethylthio-substituted tryptanthrins

Scheme 62. Visible-light-mediated trifluoromethylselenolation of indoles

Scheme 63. Trifluoromethoxylation of (hetero)arenes with bis(trifluoromethyl)peroxide

Scheme 64. Synthesis of perfluorinated isoquinolinediones

Scheme 65. Reaction of methacryloyl benzamides with perfluoroalkyl iodides

Scheme 66. Three-component [3+2+1] heteroannulation for synthesis of perfluoroalkylated pyrimidine

Scheme 67. Synthesis of perfluoroalkylated 2H-azirines

Scheme 68. Synthesis of perfluoroalkylated benzimidazo[2,1- α]isoquinoline-6(5H)-ones and indolo[2,1-α]isoquinolin-6(5H)-ones

Scheme 69. Mechanism for synthesis of perfluoroalkylated benzimidazo[2,1-α]isoquinoline-6(5H)-ones

Scheme 70. The four-component [2+1+1+1] cyclization synthesis of perfluoroalkyl isoxazoles

Scheme 71. C—H Difluoromethylation of heteroarene substrates

Scheme 72. Comparison of trifluoromethylation under electrochemical and TBHP radical initiation

Scheme 73. Trifluoromethylation of electron-deficient heterocycles mediated by bromide ions

Scheme 74. Ni-catalyzed perfluoroalkylation with of (hetero)arenes

Scheme 75. Electrophotochemical C—H trifluoromethylation of (hetero)arenes

Scheme 76. Mechanism for electrophotochemical C—H trifluoromethylation of (hetero)arenes

Scheme 77. Electrochemical fluoroalkylation of indole derivatives

Scheme 78. Copper-catalyzed C—H difluoroalkylation of coumarins with fluoroalkyl bromides

Scheme 79. Alternating current electrolytic trifluoromethylation of (hetero)arenes

Scheme 80. Perfluoroalkylation of the imidazo[1,2-α]pyridines with perfluoroalkyl iodides

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