自由基参与的烯烃C—CF3/C—N键形成反应研究进展

doi:10.6023/cjoc202208026

摘要/Abstract

烯烃的双官能团化反应是当前有机合成领域的研究热点. 这些反应可以快速、经济的在烯烃的碳-碳双键(C=C)上引入两个相同或不同的基团, 从而增加分子的复杂性和应用价值. 三氟甲基对有机化合物的亲脂性、渗透性和代谢稳定性等性质有重要影响, 同时C—N键广泛存在于各种有机分子结构中. 通过烯烃的双官能团化同时构建C—CF₃和C—N键, 在有机合成和药物化学领域具有重要意义. 按照不同“N”源进行分类, 综述了近年来自由基参与的烯烃C—CF₃和C—N键形成反应的研究进展, 阐述了可能经历的自由基化学反应历程, 对其应用前景进行了展望.

关键词: 自由基, 烯烃, 三氟甲基, C—N键

Bifunctionalization of alkenes is a hot topic in organic synthesis, which can introduce different functional groups into the carbon-carbon double bond (C=C) of olefins quickly and economically, thereby increasing the complexity and application value of molecules. The trifluoromethyl groups can influence lipophilicity, permeability, and metabolic stability of organic compounds. Meanwhile, C—N bond widely exists in various organic molecules. The construction of C—CF₃/C—N bond simultaneously through bifunctionalization of alkenes is of great significant in the field of organic synthesis and medicinal chemistry. In this review, we focus on the progress in C—CF₃/C—N bond formation reactions of alkenes involving free radical intermediates based on different “N” sources. The possible radical reaction mechanism and their possible applications are also highlighted.

Key words: free radicals, alkenes, trifluoromethyl groups, C—N bond

引用此文

郑绿茵, 王逸涵, 蔡刘欢, 郭维. 自由基参与的烯烃C—CF₃/C—N键形成反应研究进展[J]. 有机化学, 2022, 42(12): 4078-4098.

Lüyin Zheng, Yihan Wang, Liuhuan Cai, Wei Guo. Progress in C—CF₃/C—N Bond Formation Reactions of Alkenes Involving in Free Radicals[J]. Chinese Journal of Organic Chemistry, 2022, 42(12): 4078-4098.

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图/表 39

图式1. 烯烃的C—CF3/C—N键形成反应

Scheme 1. C—CF3/C—N Bond formation reactions of alkenes

图式2. 铜催化N-中心自由基诱导的烯烃胺基三氟甲基化

Scheme 2. Copper-catalyzed N-centered radical-induced aminotrifluoromethylation of alkenes

图式3. 光催化烯烃的胺基三氟甲基化

Scheme 3. Photocatalytic aminotrifluoromethylation of alkenes

图式4. 无金属的光催化烯烃胺基三氟甲基化

Scheme 4. Precious metal-free photocatalytic aminotrifluoromethylation of alkenes

图式5. 光诱导铜催化烯烃的胺基三氟甲基化

Scheme 5. Photoinduced copper-catalyzed aminotrifluoromethylation of alkenes

图式6. Lewis酸Sc(OTf)3和可见光协同催化的烯烃胺基三氟甲基化

Scheme 6. Synergistic Lewis acid and photoredox-catalyzed aminotrifluoromethylation of alkenes

图式7. 恒流电解与Lewis酸协同催化的烯烃胺基三氟甲基化

Scheme 7. Constant current electrolysis synergizing with a Lewis-acid catalysis protocol for the aminotrifluoromethylation of alkenes

图式8. 无金属电催化的烯烃胺基三氟甲基双官能团化

Scheme 8. Metal-free electrocatalytic difunctionalization of alkene aminotrifluoromethyl

图式9. 铜催化烯烃的叠氮基三氟甲基化

Scheme 9. Copper-catalyzed azidotrifluoromethylation of alkenes

图式10. 铜催化三组分烯烃的叠氮基三氟甲基化

Scheme 10. Copper-catalyzed three-component azidotrifluoromethylation of alkenes

图式11. 铜催化烯烃的叠氮基三氟甲基化

Scheme 11. Copper-catalyzed azidotrifluoromethylation of alkenes

图式12. 铜催化烯酰胺不对称叠氮基三氟甲基化

Scheme 12. Copper-catalyzed asymmetric azidotrifluoromethylation of acrylamides

图式13. 铁催化天然产物的叠氮基三氟甲基化

Scheme 13. Iron-catalyzed azidotrifluoromethylation of natural products

图式14. 铁催化烯烃的叠氮基三氟甲基化

Scheme 14. Iron-catalyzed azidotrifluoromethylation of olefins

图式15. 铁催化烯烃/炔烃的叠氮基三氟甲基化

Scheme 15. Iron-catalyzed azidotrifluoromethylation of alkenes/ alkynes

图式16. 铁催化烯烃的不对称叠氮基三氟甲基化

Scheme 16. Iron-catalyzed asymmetric azidotrifluoromethylation of styrenes

图式17. 铁催化烯烃的不对称叠氮基三氟甲基化

Scheme 17. Iron-catalyzed asymmetric azidotrifluoromethylation of styrenes

图式18. 锰催化烯烃的叠氮基三氟甲基化

Scheme 18. Manganese-catalyzed azidotrifluoromethylation of alkenes

图式19. 无金属催化烯烃的叠氮基三氟甲基化

Scheme 19. Metal-free azidotrifluoromethylation of alkenes

图式20. 光催化烯胺甲酸酯的叠氮基三氟甲基化

Scheme 20. Photocatalytic azidotrifluoromethylation of enecarbamates

图式21. 光催化烯烃的叠氮基三氟甲基化

Scheme 21. Photoredox-catalyzed azidotrifluoromethylation of alkenes

图式22. 光催化烯烃的叠氮基三氟甲基化

Scheme 22. Photoredoxcatalyzed azidotrifluoromethylation of alkenes

图式23. 光诱导、铜催化烯烃的叠氮基三氟甲基化

Scheme 23. Photoinduced, copper-catalyzed azidotrifluoromethylation of alkenes

图式24. 光催化烯烃的叠氮基三氟甲基化

Scheme 24. Photocatalyzed azidotrifluoromethylation of alkenes

图式25. 光催化烯烃的偶氮基三氟甲基化

Scheme 25. Photocatalytic azotrifluoromethylation of alkenes

图式26. 光催化烯烃的三氟甲基肼基化

Scheme 26. Photocatalytic trifluoromethyl-hydrazination of alkenes

图式27. 铜催化的烯胺分子内胺基三氟甲基化环化反应

Scheme 27. Copper-catalyzed intramolecular aminotrifluoromethylative cyclization of allylamines

图式28. 铜催化非活化烯烃分子内胺基三氟甲基化环化反应

Scheme 28. Copper-catalyzed intramolecular aminotrifluoromethylative cyclization of unactivated alkenes

图式29. 双催化策略烯胺的不对称自由基胺基三氟甲基化环化反应

Scheme 29. Direct asymmetric radical aminotrifluoromethylative cyclization of enamines through a dual-catalytic strategy

图式30. 不对称催化烯胺的自由基胺基三氟甲基化环化反应

Scheme 30. Catalytic asymmetric radical aminotrifluoromethlative cyclization of enamines

图式31. 铜催化烯胺的分子内胺基三氟甲基化环化反应

Scheme 31. Copper-catalyzed intramolecular aminotrifluoromethylative cyclization of enamines

图式32. 铜催化β,γ-不饱和腙的三氟甲基化环化反应

Scheme 32. Copper-catalyzed trifluoromethylative cyclization of β,γ-unsaturated hydrazones

图式33. 铜催化氧代高烯丙基苯亚胺酯的分子内胺基三氟甲基化环化反应

Scheme 33. Copper-catalyzed intramolecular aminotrifluoromethylative cyclization of O-homoallyl benzimidates

图式34. 光催化烯丙胺的分子内三氟甲基化环化反应

Scheme 34. Photocatalytic intramolecular trifluoromethylation/ cyclization of allylic amines

图式35. 光催化不饱和腙或肟的分子内三氟甲基化环化反应

Scheme 35. Photocatalytic intramolecular trifluoromethylation/ cyclization of unsaturated hydrazones or oximes

图式36. 光催化区域选择性含有酰胺侧链的环烯烃三氟甲基化螺环化反应

Scheme 36. Photocatalytic regioselective trifluoromethylative spirocyclization of cyclic alkenes containing an amide pendant

图式37. 光催化烯胺的三组分串联反应

Scheme 37. Photocatalytic three-component tandem reaction of vinylimines

图式38. 电催化烯胺的三氟甲基化串联环化反应

Scheme 38. Electrochemical tandem trifluoromethylative cyclization of allylamines

图式39. 电催化氮烯醇的分子内三氟甲基化环化反应

Scheme 39. Electrochemical intramolecular trifluoromethylative cyclization of N-tethered alkenyl alcohols

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自由基参与的烯烃C—CF₃/C—N键形成反应研究进展

Progress in C—CF₃/C—N Bond Formation Reactions of Alkenes Involving in Free Radicals

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