单/二/多氟烷基醚的合成研究进展

doi:10.6023/cjoc202401003

摘要/Abstract

含氟烷基醚广泛应用于有机化学、材料科学、环境科学和生命科学等领域, 尤其在生物医药领域, 引入氟烷氧基能提高代谢稳定性、改善细胞膜通透性, 从而明显改善生物活性分子的药效学和药代动力学特性而备受关注. 尽管已经报道了多种构建含氟烷基醚的策略, 市场上含氟烷基醚类药物和农用化学品的数量仍然很少, 因此, 开发制备含氟烷基醚类化合物的有效方法是一项需求很大且挑战性较强的工作. 主要从C—O键偶联间接氟烷氧基化、C(sp²)—H、C(sp²)—C、C(sp³)—X(杂原子)直接氟烷氧基化和其它直接氟烷氧基化方面, 分类总结了合成单氟甲基醚、二氟甲基醚和多氟烷基醚的研究进展, 并探讨了部分反应可能的机理和适用范围.

关键词: 氟烷氧基化, 单氟甲基醚, 二氟甲基醚, 多氟烷基醚

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

引用此文

宋冬雪, 赵红琼, 许颖, 汲晨锋, 刘颖杰. 单/二/多氟烷基醚的合成研究进展[J]. 有机化学, 2024, 44(7): 2174-2203.

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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图/表 42

图1. 氟烷氧基化医药和农药

Figure 1. Selected examples of fluoroalkoxylated pharmaceuticals and pesticides

图式1. 酚类、羧酸及磺酸的单氟甲基化反应

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

图式2. N-甲苯磺酰基-S-氟甲基-S-苯基磺酰亚胺的制备

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

图式3. PhSO(NTs)CH2F与O中心亲核底物的直接单氟甲基化反应

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

图式4. 单氟甲基取代磺酰叶立德试剂的制备(a)和单氟甲基取代磺酰叶立德试剂介导的亲电单氟甲基化反应(b)

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

图式5. ICH2F与O、S和Se中心亲核底物的单氟甲基化反应

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

图式6. 单氟甲基锍叶立德试剂的制备(a)和锍叶立德试剂介导的亲电单氟甲基化反应(b)

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

图式7. 早期合成二氟甲基芳基醚的常见方法

Scheme 7. Early common approaches of difluoromethyl aryl ethers formation

图式8. 早期合成二氟甲基烷基醚的常见方法

Scheme 8. Early common approachs of difluoromethyl alkyl ethers formation

图式9. DMBDT-BF4的一锅法制备(a)和DMBDT-BF4与AgF介导的醇类二氟甲基化反应(b)

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

图式10. 醇类的机械化学二氟甲基化反应

Scheme 10. Mechanochemical difluoromethylations of alcohols

图式11. 早期合成三氟乙基芳基醚的经典方法

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

图式12. 全氟烷基醚的合成

Scheme 12. Synthesis of perfluoroalkyl ethers

图式13. 钌催化芳烃及杂芳烃的多氟烷氧基化反应

Scheme 13. Ruthenium-catalyzed polyfluoroalkoxylation of arenes and heteroarenes

图式14. 单氟甲氧基化试剂的电化学合成(a)和?OCH2F自由基源介导的芳烃C(sp2)—H单氟甲氧基化反应(b)

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

图式15. 二氟甲氧基化试剂的制备(a)和?OCHF2自由基源介导的(杂)芳烃C(sp2)—H直接二氟甲氧基化反应(b)

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

图式16. TEMPO?催化的(杂)芳烃C(sp2)—H二氟甲氧基化反应

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

图式17. N-二氟甲氧基-4-氰基吡啶鎓三氟甲磺酸胺作为自由基源的(杂)芳烃C(sp2)—H二氟甲氧基化反应

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

图式18. 过渡金属、有机光催化剂介导的喹喔啉酮C(3) 过渡金属、有机光催化剂介导的喹喔啉酮C(3)—H氟烷氧基化反应(a)和CF3SO2Na介导的喹喔啉酮C(3)—H氟烷氧基化反应(b)

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

图式19. N-七氟异丙氧基苯并三唑鎓盐的合成(a)和(杂)芳烃C(sp2)—H的自由基七氟异丙氧基化反应(b)

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

图式20. 钯催化苯甲醛的脱氢氟烷氧基化反应

Scheme 20. Palladium-catalyzed dehydrogenative fluoroalkoxylation of benzaldehydes

图式21. TDG控制的芳香醛位点选择性C(sp2)—H多氟烷氧基化反应

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

图式22. 钯催化3-芳基香豆素的邻位三氟乙氧基化反应

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

图式23. 钯催化4-芳基吡咯并[2,3-d]嘧啶的芳烃邻位C(sp2)—H氟烷氧基化反应

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

图式24. 钯催化4-芳基吡咯并[2,3-d]嘧啶的双氟烷氧基化反应

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

图式25. FMBT作为?OCH2F自由基源的烯烃的氨基单氟甲氧基化反应

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

图式26. FMBT作为?OCH2F自由基源的烯烃的其它单氟甲氧基化反应

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

图式27. 钯催化未活化烯烃的分子间双三氟甲氧基化反应

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

图式28. 光氧化还原催化芳基乙烯的羟基烷氧基化反应

Scheme 28. Photoredox-catalyzed hydroxyalkoxylation of aryl ethylene

图式29. α-二氟异丙氧基酮化合物的合成

Scheme 29. Synthesis of α-difluoroisopropoxy ketone compounds

图式30. N-七氟异丙氧基邻苯二甲酰亚胺的合成

Scheme 30. Synthesis of N-heptafluoroisopropoxyphthalimide

图式31. 烯烃C(sp2)—C亲核和自由基七氟异丙氧基化反应

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

图式32. 电氧化烯烃的1,2-氨基三氟乙氧基化反应

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

图式33. 全氟烷基醇阴离子介导的亲核取代反应

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

图式34. α-三氟乙氧基取代酮的合成

Scheme 34. Synthesis of α-trifluoroethoxy substituted ketones

图式35. 烷基卤化物的亲核七氟异丙氧基化反应

Scheme 35. Nucleophilic heptafluoroisopropoxylation of alkyl halides

图式36. 醇的脱氧七氟异丙氧基化反应

Scheme 36. Deoxyheptafluoroisopropoxylation of alcohols

图式37. 三氟乙氧基化芳烃的合成

Scheme 37. Synthesis of trifluoroethoxylated arenes

图式38. 多氟烷基醇阴离子介导的多氟烷基醚的合成

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

图式39. 全氟烷基苯甲酸酯的制备(a)和全氟烷基苯甲酸酯介导的芳烃的溴化全氟烷氧基化反应(b)

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

图式40. TDG控制的芳香醛位点选择性C(sp3)—H键多氟烷氧基化反应

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

图式41. 铑催化N-芳基-吡咯烷-2-酮的氧化和三氟乙氧基化反应

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

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