Progress in Visible-Light Catalyzed C—F Bond Functionalization of gem-Difluoroalkenes

doi:10.6023/cjoc202106013

Abstract

Monofluoroalkene structural units widely exist in complex functional molecules such as drugs and natural products. They are also critical organic synthons with broad applications in medicine, biology, materials and other fields. Therefore, it is of great scientific significance and practical value to develop green, economical and efficient methods for synthesizing monofluoroalkenes. Functionalization of the C—F bond of gem-difluoroalkenes is an effective method to prepare monofluoroalkenes. The research progress in C—F bond functionalization of gem-difluoroalkenes under visible-light redox catalysis and visible-light redox/transition-metal synergistic catalysis, including the substrate scope, reaction mechanism, and synthesis applications, is summarized. Finally, the prospects of this reaction are also discussed.

Key words: visible-light, monofluoroalkene, gem-difluoroalkene, C—F bond functionalization

Cite this article

Zhiqing Li, Xiaoyang Qiu, Jiang Lou, Qiang Wang. Progress in Visible-Light Catalyzed C—F Bond Functionalization of gem-Difluoroalkenes[J]. Chinese Journal of Organic Chemistry, 2021, 41(11): 4192-4207.

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Fig. & Tab. 29

Figure 1. Representative bioactive molecules containing monofluoroalkene structural units

Scheme 1. Visible-light catalyzed C—F bond functionalization of gem-difluoroalkenes

Scheme 2. Visible-light photoredox catalyzed α-aminomethyl- ation of C(sp2)—F bond

Scheme 3. Mechanistic studies of photoredox catalyzed α- aminomethylation of gem-difluoroalkenes

Scheme 4. Reaction mechanism of α-aminomethylation of gem- difluoroalkenes

Scheme 5. Photoredox-catalyzed α-monofluoroalkenylation of heteroatomic alkanes

Scheme 6. Reaction mechanism of α?monofluoroalkenylation of heteroatomic alkanes

Scheme 7. Visible-light catalyzed decarboxylative monofluoroalkenylation of α-amino acids

Scheme 8. Reaction mechanism of decarboxylative monofluoroalkenylation of α-amino acids

Scheme 9. Visible-light catalyzed decarboxylative cross-coupling of gem-difluoroalkenes with aliphatic carboxylic acids

Scheme 10. Radical clock reaction involving cyclopropylacetic acid

Scheme 11. Reaction mechanism of decarboxylative radical cross-coupling

Scheme 12. Visible-light catalyzed defluorinative alkylation of gem-difluoroalkenes

Scheme 13. Mechanism studies for visible-light promoted defluorinative alkylation of gem-difluoroalkenes

Scheme 14. Possible mechanism for visible-light promoted defluorinative alkylation of gem-difluoroalkenes

Scheme 15. Three-component tandem reactions catalyzed by visible-light

Scheme 16. Reaction mechanism of three-component tandem reactions catalyzed by visible-light

Scheme 17. Visible-light-induced selective defluoroborylation of gem-difluoroalkenes

Scheme 18. Reaction mechanism of selective defluoroborylation

Scheme 19. Visible-light/palladium co-catalyzed C—F bond carboxylation

Scheme 20. Defluorocarboxylation of aryl ketones

Scheme 21. Mechanistic studies of defluorocarboxylation of aryl ketones

Scheme 22. Reaction mechanism of defluorocarboxylation of aryl ketones

Scheme 23. Visible-light catalyzed trifluoromethylation of C—F bond of gem-difluoroalkenes

Scheme 24. Reaction mechanism for trifluoromethylation of C—F bond of gem-difluoroalkenes

Scheme 25. Visible-light catalyzed defluorinative cross-coupling of gem-difluoroalkenes with thiols

Scheme 26. Reaction mechanism for the defluorinative cross- coupling of gem-difluoroalkenes with thiols

Scheme 27. Visible-light catalyzed the synthesis of α-fluoro- β-arylalkenyl sulfides

Scheme 28. Reaction mechanism for the synthesis of α-fluoro- β-arylalkenyl sulfides

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