Recent Advances in Transition-Metal Catalyzed C—H Bond Activation for the Synthesis of C(sp3)-Fluoroalkyl Compounds

doi:10.6023/cjoc202406033

Abstract

Transition-metal catalyzed insert C—H bond activation has gained great attention for the last decades, which would provide a straightforward and attractive strategy for the synthesis of organofluorine compounds. Compared with aryl and alkynyl fluoroalkyl compounds, the synthesis of C(sp³)-fluoroalkyl compounds through C—H bond activation still lag behind. This review highlights the recent advances in the synthesis of alkyl fluoroalkyl compounds through the transition-metal (Rh, Ru, Pd, Cu, Ir, Ni, Mn, etc.) catalyzed C—H bond activation. The very recently developed chiral fluorinated compound synthesis through asymmetric C—H bond activation is included.

Key words: C—H bond activation, transition-metal catalyst, C(sp³)-fluoroalkyl compounds

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Manman Wang, Wenhui Xi, Hao Wu, Dachang Bai. Recent Advances in Transition-Metal Catalyzed C—H Bond Activation for the Synthesis of C(sp³)-Fluoroalkyl Compounds[J]. Chinese Journal of Organic Chemistry, 2025, 45(2): 516-530.

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Fig. & Tab. 32

Scheme 1. Types of established C—H bond activation mechanisms

Scheme 2. Transition-metal catalyzed C—H bond activation for the synthesis of C(sp3)-fluoroalkyl containing compounds

Scheme 3. Rh(III)-catalyzed cyclization reaction of 1-aryl-2,2,2-trifluorodiazoethanes

Scheme 4. Rh(III)-catalyzed coupling reaction of arenes with methyl 2-diazo-3,3,3-trifluoropropanoate

Scheme 5. Rh(III)-catalyzed olefination of carboxamides with trifluoromethyl allylic carbonate

Scheme 6. Rh(III)-catalyzed coupling reaction of α-trifluoromethylacrylic acid with benzamides

Scheme 7. Rhodium(III)-catalyzed C(sp2)—H bond activation and coupling with β-CF3-substituted enones

. Schem 8 Rhodium(III)-catalyzed addition and cyclization reaction of gem-difluorovinyl tosylate

Scheme 9. Rh(III)-catalysed C—H couplings of arenes with gem-difluoromethylene alkynes

Scheme 10. Ru(II)-catalyzed C—H activation of aryl nitrones and coupling with perfluoroalkylolefins

Scheme 11. Nickel catalyzed C—H trifluoroethylation of arenes

Scheme 12. Nickel-catalyzed direct C—H trifluoroethylation of indoles

Scheme 13. Copper-catalyzed chemoselective C—H functionalization of quinoxalin-2(1H)-ones with hexafluoroisopropanol

Scheme 14. Copper-catalyzed trifluoromethylation of unactivated cycloalkenes

Scheme 15. Copper-catalyzed oxidative trifluoromethylation of benzylic sp3 C—H of tetrahydroisoquinoline derivatives

Scheme 16. Copper-catalyzed benzylic C—H trifluoromethylation of phenol derivatives

Scheme 17. Copper-mediated trifluoromethylation of benzylic C(sp3)—H bonds

Scheme 18. Copper-catalyzed C(sp3)—H trifluoromethylation of benzyl substrates

Scheme 19. Copper-catalyzed C(sp3)—H trifluoromethylation of alkanes

Scheme 20. Merger of decatungstate photocatalysis with copper catalysis to enable aliphatic C(sp3)—H trifluoromethylation

Scheme 21. Copper(II)-catalyzed radical trifluoroethylation through the C(sp3)—H functionalization

Scheme 22. Copper-catalyzed allyl C—H bond activation for the synthesis of allyl trifluoromethyl compounds

Scheme 23. Cu-catalyzed C—H trifluoromethylation of 3-arylprop-1-ynes

Scheme 24. Mn-catalyzed C(sp3)—H bond peroxidation

Scheme 25. Copper-catalyzed chloroamide-directed benzylic C—H difluoromethylation

Scheme 26. Pd-catalyzed C(sp3)—H trifluoroethylation

Scheme 27. Palladium-catalyzed ethoxylation of aliphatic C—H bond

Scheme 28. (R)-CpRh-catalyzed asymmetric addition of C—H bond to ethyl trifluoropyruvate

Scheme 29. chiral Rh(III) catalyzed the asymmetric trifluoromethyl alkylation reaction of aryl C—H bond

Scheme 30. Rh-catalyzed asymmetric insertion of fluoroalkyl carbene into ether α-C(sp3)—H bonds

Scheme 31. Ir-catalyzed asymmetric addition of N-methyl C—H bond to α-trifluoromethylstyrenes

Scheme 32. Cu-catalyzed asymmetric benzylic C—H trifluoromethylation

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过渡金属催化碳氢键活化合成烷基氟烷基化合物的研究进展

Recent Advances in Transition-Metal Catalyzed C—H Bond Activation for the Synthesis of C(sp³)-Fluoroalkyl Compounds

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