Difluorinated Silyl Enol Ethers as Fluorine-Containing Building Blocks for the Synthesis of Organofluorine Compounds

doi:10.6023/cjoc202204060

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (11): 3562-3587.DOI: 10.6023/cjoc202204060 Previous Articles Next Articles

Special Issue: 有机氟化学虚拟合辑

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二氟烯醇硅醚作为含氟砌块在构建有机氟化物中的研究进展

郭檬檬^a, 于子伦^a, 陈玉兰^a, 葛丹华^a^,^*(), 马猛涛^b, 沈志良^a, 褚雪强^a^,^*()

^a南京工业大学化学与分子工程学院先进化学制造研究院南京 211816
^b南京林业大学理学院南京 210037

收稿日期:2022-04-25 修回日期:2022-06-24 发布日期:2022-07-13
通讯作者: 葛丹华, 褚雪强
作者简介:
†作者对文章贡献一致
基金资助:
南京工业大学(39837146); 南京工业大学(39837118); 国家自然科学基金(22001121); 江苏省自然科学基金(BK20180690)

Difluorinated Silyl Enol Ethers as Fluorine-Containing Building Blocks for the Synthesis of Organofluorine Compounds

Mengmeng Guo^a, Zilun Yu^a, Yulan Chen^a, Danhua Ge^a(), Mengtao Ma^b, Zhiliang Shen^a, Xueqiang Chu^a()

^aInstitute of Advanced Synthesis, School of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing 211816
^bCollege of Science, Nanjing Forestry University, Nanjing 210037

Received:2022-04-25 Revised:2022-06-24 Published:2022-07-13
Contact: Danhua Ge, Xueqiang Chu
About author:
†These authors contributed equally to this work.
Supported by:
Nanjing Tech University(39837146); Nanjing Tech University(39837118); National Natural Science Foundation of China(22001121); National Natural Science Foundation of Jiangsu Province(BK20180690)

Organofluorine compounds have been widely applied in various fields ranging from drug discovery, clinical medicines, agrochemistry, and materials science to organic synthesis, due to their special chemical and physical properties when compared with nonfluorinated analogs. In the past decades, significant progress has been made in the development of selective fluorination and fluoroalkylation for the synthesis of structurally diverse fluorine-containing molecules. Among them, the α-fluoroalkylated carbonyl group represents an important class of scaffold components in biologically active and druglike compounds. In this context, based on the use of difluorinated silyl enol ether (DFSEE) as a unique fluoroaklylating reagent, a variety of methods for the incorporation of gem-difluoroalkylated carbonyl moiety have been achieved, including aldol, Mannich, arylation, allylation, protonation, halogenation, conjugate addition, and olefination reactions. On the other hand, DFSEEs could also merge with new types of reactions such as radical-type difluoroalkylation and cascade reaction by virtue of their incredible reactive flexibility. In addition, the O-site selective addition of DFSEEs was also reported, enabling the construction of versatile gem-difluoroalkenes. Given the importance of organofluorine compounds and the synthetic potential of these avenues, herein, we highlight the recent advances in the functionalization of gem-difluorinated silyl enol ethers, which serve as key fluorine-containing building blocks for the synthesis of organofluorine compounds.

Key words: difluorinated silyl enol ether, fluorine-containing building block, fluorinated compounds, difluoroalkylation, organofluorine chemistry

Cite this article

Mengmeng Guo, Zilun Yu, Yulan Chen, Danhua Ge, Mengtao Ma, Zhiliang Shen, Xueqiang Chu. Difluorinated Silyl Enol Ethers as Fluorine-Containing Building Blocks for the Synthesis of Organofluorine Compounds[J]. Chinese Journal of Organic Chemistry, 2022, 42(11): 3562-3587.

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Fig. & Tab. 31

Scheme 1. Representative biologically active molecules and drugs featuring an α-difluorinated carbonyl unit

Scheme 2. Reported methods for the construction of α,α- difluorocarbonyl compounds

Scheme 3. Methods for the synthesis of DFSEE

Scheme 4. General reaction manifolds involving difluorinated silyl enol ethers (DFSEEs)

Scheme 5. Highly efficient “on water” catalyst-free nucleophilic addition reactions using fluorinated silyl enol ethers

Scheme 6. HClO4-catalysed aldol-type reaction of fluorinated silyl enol ethers with acetals or ketals

Scheme 7. HFIP-catalyzed Mukaiyama-aldol reaction of glyoxal monohydrates with fluorinated silyl enol ethers

Scheme 8. p-Toluenesulfonic acid-catalyzed reaction of phthalaldehydic acids with fluorinated silyl enol ethers

Scheme 9. Sc(OTf)3 catalyzed Mukaiyama-Mannich reaction of fluorinated silyl enol ethers with unactivated ketimines

Scheme 10. The ortho-difluoroalkylation of aryliodanes with fluorinated silyl enol ethers

Scheme 11. Dearomatization of aryl sulfoxides with fluorinated silyl enol ethers

Scheme 12. Intermolecular Pummerer reaction of alkyl sulfoxides with fluorinated silyl enol ethers

Scheme 13. Copper-catalyzed highly enantioselective difluoroalkylation of secondary propargyl sulfonates with fluorinated silyl enol ethers

Scheme 14. Trifluoromethylthiolation, trifluoromethylation, and arylation reactions of fluorinated silyl enol ethers

Scheme 15. Catalytic enantioselective synthesis of difluoromethylated tetrasubstituted stereocenters in isoindolones enabled by a multiple-fluorine system

Scheme 16. Construction of β?quaternary α,α-difluoroketones via tertiary alcohols with fluorinated silyl enol ethers

Scheme 17. HFIP-catalyzed direct dehydroxydifluoroalkylation of benzylic and allylic alcohols with fluorinated silyl enol ethers

Scheme 18. HFIP-catalyzed difluoroalkylation of propargylic alcohols to access tetrasubstituted difluoroalkyl allenes

Scheme 19. Regioselective Markovnikov hydrodifluoroalkylation of alkenes using fluorinated silyl enol ethers

Scheme 20. Reversal of regioselectivity in nucleophilic difluoroalkylation of α,β-enones employing silylium catalyst

Scheme 21. Visible-light-initiated difluoromethylation of arene diazonium tetrafluoroborates

Scheme 22. Visible light promoted deaminative difluoroalkylation of aliphatic amines with fluorinated silyl enol ethers

Scheme 23. Photoredox-catalyzed sulfonylation of fluorinated silyl enol ethers with the insertion of sulfur dioxide

Scheme 24. Decarboxylative and deaminative alkylation of fluorinated silyl enol ethers via photoredox catalysis

Scheme 25. Iron-catalyzed cyanoalkylation of fluorinated silyl enol ethers with cyclobutanone oxime esters

Scheme 26. Photoredox-catalyzed difluoroalkylation of fluorinated silyl enol ethers with fluoroalkyl halides

Scheme 27. Construction of gem-difluoroenol esters through catalytic O?selective addition of fluorinated silyl enol ethers to ketenes

Scheme 28. Catalyst-free and solvent-controlled divergent synthesis of difluoromethylene-containing S?heterocycles

Scheme 29. Cascade cyclization of azadienes with fluorinated silyl enol ethers

Scheme 30. HFIP-catalyzed highly diastereoselective [4＋2] cyclization

Scheme 31. Divergent synthesis of gem-difluorinated oxa-spirocyclohexadienones by p?hydroxybenzyl alcohols with fluorinated silyl enol ethers

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二氟烯醇硅醚作为含氟砌块在构建有机氟化物中的研究进展

Difluorinated Silyl Enol Ethers as Fluorine-Containing Building Blocks for the Synthesis of Organofluorine Compounds

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