Progress in Fluoroalkylation of Multicomponent

doi:10.6023/cjoc202007025

Abstract

Multi-component fluoroalkylation is a hot topic in organic fluorine chemistry. In the past few years, due to the development of new reagents and new methods, multi-component fluoroalkylation reactions have made great progress. It can not only introduce fluoroalkyl groups with other functional groups in one step economically and effectively, but also transform the starting materials into a variety of compounds with biological or pharmaceutical. The development of multi-component fluoroalkylation over the past decade is reviewed from seven parts: three-component difluoroalkylation reaction, three-component trifluoroalkylation reaction, three-component perfluoroalkylation reaction, three-component monofluoro- alkylation reaction, three-component fluorination and four-component fluoroalkylation and conclusion. At the same time, this kind of reaction is summarized and prospected.

Key words: multicomponent, bifunctionalization, difluoroalkylation, trifluoromethylation, perfluoroalkylation, monofluoroalkylation, fluorination

Cite this article

Jun Pan, Jingjing Wu, Fanhong Wu. Progress in Fluoroalkylation of Multicomponent[J]. Chinese Journal of Organic Chemistry, 2021, 41(3): 983-1001.

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Fig. & Tab. 68

Scheme 1. Hydroxydifluoromethylation of styrenes using photoredox catalysis

Scheme 2. Aryldifluoroalkylation of styrenes using photoredox catalysis

Scheme 3. Ir(ppy)3/FeCl2 catalyzed suldifluoroalkylation of alkenes

Scheme 4. 1,6-Difunctionalization of unactivated alkenes using photoredox catalysis

Scheme 5. Photocatalyzed cyanodifluoromethylation of alkenes

Scheme 6. Ni-catalyzed aryldifluoroalkylation of alkenes

Scheme 7. Ni-catalyzed alkyldifluoroalkylation of alkenes

Scheme 8. Ni-catalyzed carbofluoroalkylation of 1,3-enynes

Scheme 9. Cu-catalyzed suldifluoroalkylation of actived alkenes

Scheme 10. Co-catalyzed peroxidedifluoroalkylation of alkenes

Scheme 11. Pd-catalyzed aryldifluoroalkylation of alkynes

Scheme 12. Cu-catalyzed cyano-difluoroalkylation of alkynes

Scheme 13. Pd-catalyzed phosphinodifluoroalkylation of alkynes

Scheme 14. Pd-catalyzed aryldifluoroalkylation of alkynes

Scheme 15. Pd-catalyzed fluoroalkylboration of alkynes

Scheme 16. Pd-catalyzed difluoroalkylboration of alkynes

Scheme 17. Drugs containing trifluoromethyl group

Scheme 18. Oxygentrifluoromethylation of alkenes using photoredox catalysis

Scheme 19. Oxygentrifluoromethylation of alkenes

Scheme 20. Cu-catalyzed difunctionalization of alkene-amide

Scheme 21. Ru-catalyzed difunctionalization of alkene-amide

Scheme 22. Metal-free trifluoromethylation of alkenes

Scheme 23. Cu-catalyzed oxygentrifluoromethylatio of alkene- amide

Scheme 24. Cu-catalyzed intermolecular trifluoromethylation of alkenes

Scheme 25. Ru-catalyzed azidotrifluoromethylation and aminotrifluoromethylation of alkenes

Scheme 26. Cu-catalyzed azidotrifluoromethylation of alkenes

Scheme 27. Iron-catalyzed azidotrifluoromethylation of olefins and N-heterocycles

Scheme 28. Cu-catalyzed trifluoromethylthiocyanation of alkenes

Scheme 29. Sultrifluoromethylation of terminal alkenes using photoredox catalysis

Scheme 30. Cu-catalyzed cyanotrifluoromethylation of alkenes

Scheme 31. Cu-catalyzed cyanotrifluoromethylation of alkenes

Scheme 32. Cu-catalyzed enantioselective cyanotrifluoromethylation of alkenes

Scheme 33. Cu-catalyzed enantioselective 1,5-cyanotrifluoro- methylation of vinylcyclopropanes

Scheme 34. Ru-catalyzed Trifluoromethylation of Alkenes

Scheme 35. Cu-catalyzed cyanofluoroalkylation of alkenes

Scheme 36. Cu-catalyzed cyanotrifluoromethylation of 1,3- enynes

Scheme 37. Cu-catalyzed aryltrifluoromethylation of alkenes

Scheme 38. Cu-catalyzed aryltrifluoromethylation of aryl-eth- ylene

Scheme 39. Cu-catalyzed difunctionalization of alkenes with CO2

Scheme 40. Metal-free alkynyltrifluoromethylation of unactived Alkenes

Scheme 41. Cu-catalyzed alkynyltrifluoromethylation of actived alkenes

Scheme 42. Acyltrifluoromethylation of alkenes using NHC catalysis

Scheme 43. Cu-catalyzed synthesis of β-trifluoromethylated acrylonitriles and trifluoromethyl-substituted 2H-azirines

Scheme 44. Cu-catalyzed trifluoromethylation of alkynes

Scheme 45. Cu-catalyzed fluoroalkylation of alkynes

Scheme 46. Cu-catalyzed sultrifluoromethylation of arylboronic acid

Scheme 47. Metal-free boronperfluoroalkylation of unactived alkenes

Scheme 48. Metal-free α-perfluoroalkyl-β-heteroarylation of unactived alkenes

Scheme 49. Ni-catalyzed difunctionalization of alkenes

Scheme 50. Pd-catalyzed nitrogenperfluoroalkylation of alkenes and alkynes

Scheme 51. Cu-catalyzed difunctionalization of 1,3-enynes

Scheme 52. [3+2+1]-Annulation using photoredox catalysis

Scheme 53. Perfluoroalkylation of Triisopropylsilane using photoredox catalysis

Scheme 54. Cu-catalyzed three components cyanofluoroalkylation of alkenes

Scheme 55. Cu-catalyzed three components azidofluoroalkylation of alkenes

Scheme 56. Cu-catalyzed photoredox asymmetric cyanofluoroalkylation of alkenes

Scheme 57. Pd-catalyzed arylperfluoroalkylation of terminal alkynes

Scheme 58. Pd-catalyzed arylperfluoroalkylation of alkynes

Scheme 59. Pd-catalyzed arylperfluoroalkylation of alkynes

Scheme 60. Pd-catalyzed difunctionalization of alkynes

Scheme 61. Drug molecules ccontaining fluorinated tertiary and quaternary carbons

Scheme 62. Cu-catalyzed boronmonofluoromethylation of alkene

Scheme 63. Silver-catalyzed phosphonofluorination of unactivated alkenes

Scheme 64. Pd-catalyzed estermonofluoroalkylation of aryl- ethylene

Scheme 65. Aminotrifluoromethylation of alkenes using photoredox catalysis

Scheme 66. Co-catalyzed fluoroalkylation and Kornblum- DeLaMare reaction of styrenes

Scheme 67. Pd-catalyzed carbonyldifluoroalkylation of alkynes

Scheme 68. Pd-catalyzed carbonyldifluoroalkylation/carbonyl- perfluoroalkylation of alkynes

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多组分参与的氟烷基化反应研究进展