SCF3 Radical Initiated Cascade Reaction of Unsaturated Hydrocarbon

doi:10.6023/cjoc202203041

Abstract

Fluorinated compounds have been widely used in pharmaceuticals, pesticides and other disciplines due to their special physical and chemical properties, which motivates the frequent introduction of fluorinated functionalities into lead compounds to improve their physical and chemical properties. The trifluoromethylthio (SCF₃) group with high electronegativity and special lipophilicity plays an important role in a multitude of fluorinated compounds. The recent progress in the field of cascade reaction of unsaturated hydrocarbon initiated by SCF₃ radical, including reaction design, reaction mechanism and outlook, is summarized.

Key words: trifluoromethylthiolation, unsaturated hydrocarbon, cascade reaction, radical, difunctionalization

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Yun Shi, Ting Xiao, Dong Xia, Wenchao Yang. SCF₃ Radical Initiated Cascade Reaction of Unsaturated Hydrocarbon[J]. Chinese Journal of Organic Chemistry, 2022, 42(9): 2715-2727.

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Fig. & Tab. 22

Scheme 1. SCF3 radical initiated cascade reaction of unsaturated hydrocarbon

Scheme 2. Synthesis of trifluoromethylthiolated oxindoles

Scheme 3. Synthesis of trifluoromethylthiolated [2,1-a]isoquinolines and quinolinones

Scheme 4. Visible-light-promoted trifluoromethylthiolation of olefins

Scheme 5. Trifluoromethylthiolation of methylenecyclopropanes

Scheme 6. Synthesis of SCF3-substituted benzimidazole[2,1-a]isoquinolines

Scheme 7. Synthesis of SCF3-substituted tryptanthrins

Scheme 8. Synthesis of trifluoromethylthiolated indenones

Scheme 9. Synthesis of trifluoromethylthiolated thioflavones and benzothiophenes

Scheme 10. Trifluoromethylthiolation/radical cyclization of 1,6-enynes

Scheme 11. Synthesis of trifluoromethylthiolated coumarins

Scheme 12. Synthesis of trifluoromethylthiolated spiro[4,5]trienones

Scheme 13. Trifluoromethylthiolation of N-[(3-aryl)propioloyl]indoles

Scheme 14. Electrochemical trifluoromethylthiolation

Scheme 15. Synthesis of vinyl trifluoromethyl thioethers

Scheme 16. Synthesis of vinyl trifluoromethyl thioethers

Scheme 17. Synthesis of vinyl trifluoromethyl thioethers and α-trifluoromethylthio acetophenons

Scheme 18. Hydrotrifluoromethylthiolative reaction of unactivated alkenes and alkynes with trifluoromethanesulfonic anhydride

Scheme 19. Photocatalyzed radical trifluoromethylthiolation- boration of alkynes

Scheme 20. Difunctionalization of alkenes initiated by SCF3 radicals

Scheme 21. SCF3-radical mediated rearrangements

Scheme 22. Proposed reaction pathways of the SCF3-radical mediated rearrangements

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三氟甲硫基自由基引发不饱和烃的串联反应

SCF₃ Radical Initiated Cascade Reaction of Unsaturated Hydrocarbon

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