Advances in the Synthesis of Mono/Di/Polyfluoroalkyl Ethers

doi:10.6023/cjoc202401003

Abstract

Fluoroalkyl ethers are widely used in organic chemistry, materials science, environmental science, life science and other fields, especially in biopharmaceuticals, where the introduction of fluoroalkoxy groups has attracted much attention for their ability to improve metabolic stability and cell membrane permeability, thus significantly improving the pharmacodynamic and pharmacokinetic properties of biologically active molecules. Although several strategies for the construction of fluoroalkyl ethers have been reported, the number of fluoroalkyl ether-containing drugs and agrochemicals on the market is still small. Therefore, the development of effective methods for the preparation of fluoroalkyl ethers is a much needed and challenging task. The progress of research on the synthesis of monofluoromethyl ethers, difluoromethyl ethers, and polyfluoroalkyl ethers is categorized and summarized, mainly in terms of C—O bond-coupled indirect fluoroalkoxylation, C(sp²)—H, C(sp²)—C, C(sp³)—X (heteroatom) direct fluoroalkoxylation and other direct fluoroalkoxylation. The possible mechanisms and applicability of some reactions are also discussed.

Key words: fluoroalkoxylation, monofluoromethyl ethers, difluoromethyl ethers, polyfluoroalkyl ethers

Cite this article

Dongxue Song, Hongqiong Zhao, Ying Xu, Chenfeng Ji, Yingjie Liu. Advances in the Synthesis of Mono/Di/Polyfluoroalkyl Ethers[J]. Chinese Journal of Organic Chemistry, 2024, 44(7): 2174-2203.

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Fig. & Tab. 42

Figure 1. Selected examples of fluoroalkoxylated pharmaceuticals and pesticides

Scheme 1. Monofluoromethylation of phenols, carboxylic acids and sulfonic acids

Scheme 2. Preparation of N-tosyl-S-fluoromethyl-S-phenyl- sulfoximine

Scheme 3. Direct monofluoromethylation of PhSO(NTs)CH2F with O-centered nucleophilic substrates

Scheme 4. Preparation of monofluoromethyl-substituted sulfonium yelides (a) and electrophilic monofluoromethylation mediated by monofluoromethyl-substituted sulfonium yelides (b)

Scheme 5. Monofluoromethylation of ICH2F with O, S, and Se-centered nucleophilic substrates

Scheme 6. Preparation of monofluoromethyl sulfur ylide reagent (a) and electrophile monofluoromethylation mediated by sulfur ylide reagent (b)

Scheme 7. Early common approaches of difluoromethyl aryl ethers formation

Scheme 8. Early common approachs of difluoromethyl alkyl ethers formation

Scheme 9. One-pot preparation of DMBDT-BF4 (a), DMBDT-BF4 and AgF-mediated difluoromethylation of alcohols (b)

Scheme 10. Mechanochemical difluoromethylations of alcohols

Scheme 11. Early classical methods for the synthesis of trifluoroethyl aryl ethers

Scheme 12. Synthesis of perfluoroalkyl ethers

Scheme 13. Ruthenium-catalyzed polyfluoroalkoxylation of arenes and heteroarenes

Scheme 14. Electrochemical synthesis of monofluoromethoxylated reagents (a), and ?OCH2F radical source-mediated C(sp2)—H monofluoroalkoxylation of arenes (b)

Scheme 15. Preparation of difluoromethoxylated reagent (a), ?OCHF2 radical source-mediated direct C(sp2)—H difluoromethoxylation of (hetero) arenes (b)

Scheme 16. TEMPO?-catalyzed C(sp2)—H difluoromethoxylation of (hetero)arenes

Scheme 17. C(sp2)—H difluoromethoxylation of (hetero)arenes with N-difluoromethoxy-4-cyanopyridinium triflate reagent as difluoromethoxy radical source

Scheme 18. Transition metal, organophotocatalyst-mediated C(3)—H fluoroalkoxylation of quinoxalinones (a), CF3SO2Na-mediated C(3)—H fluoroalkoxylation of quinoxalinones (b)

Scheme 19. Synthesis of N-heptafluoroisopropoxybenzotriazolium salt (a), C(sp2)—H radical heptafluoroisopropoxylation of (hetero)- arenes (b)

Scheme 20. Palladium-catalyzed dehydrogenative fluoroalkoxylation of benzaldehydes

Scheme 21. TDG controlled site-selective C(sp2)—H polyfluoroalkoxylations of aromatic aldehydes

Scheme 22. Palladium-catalyzed ortho-trifluoroethoxylation of 3-arylcoumarins

Scheme 23. Palladium-catalyzed arene ortho C(sp2)—H fluoroalkoxylation of 4-aryl-pyrrolo[2,3-d] pyrimidines

Scheme 24. Palladium-catalyzed bis-fluoroalkoxylation of 4-arylpyrrolo[2,3-d]pyrimidines

Scheme 25. Amino monofluoromethoxylation of olefins with FMBT as the ?OCH2F radical source

Scheme 26. Other monofluoromethoxylations of olefins with FMBT as the ?OCH2F radical source

Scheme 27. Palladium-catalyzed intermolecular bis(trifluoromethoxylation) of unactivated alkenes

Scheme 28. Photoredox-catalyzed hydroxyalkoxylation of aryl ethylene

Scheme 29. Synthesis of α-difluoroisopropoxy ketone compounds

Scheme 30. Synthesis of N-heptafluoroisopropoxyphthalimide

Scheme 31. Nucleophilic and radical heptafluoroisopropoxylation of olefins C(sp2)—C

Scheme 32. Electro-oxidative 1,2-amino trifluoroethoxylation of alkenes

Scheme 33. Perfluorinated alkyl alcohol anion-mediated nucleophilic substitution reactions

Scheme 34. Synthesis of α-trifluoroethoxy substituted ketones

Scheme 35. Nucleophilic heptafluoroisopropoxylation of alkyl halides

Scheme 36. Deoxyheptafluoroisopropoxylation of alcohols

Scheme 37. Synthesis of trifluoroethoxylated arenes

Scheme 38. Synthesis of polyfluoroalkyl ethers mediated by polyfluoroalkyl alcohol anions

Scheme 39. Preparation of perfluoroalkyl benzoates (a) and perfluoroalkyl benzoates-mediated brominated perfluoroalkoxylation of arenes (b)

Scheme 40. TDG controlled site-selective C(sp3)—H bond polyfluoroalkoxylations of aromatic aldehydes

Scheme 41. Rhodium-catalyzed oxidation and trifluoroethoxylation of N-aryl-pyrrolidin-2-ones

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单/二/多氟烷基醚的合成研究进展