烯胺酮α-官能团化反应的研究进展

doi:10.6023/cjoc202207027

摘要/Abstract

烯胺酮是一类非常重要的有机合成砌块, 具有易获得、储存方便、反应多样性等优点. 更重要的是, 烯胺酮是许多杂环化合物的重要前体. 最近, 通过C-H活化对烯胺酮进行过渡金属催化或无过渡金属的α-官能团化反应已成为构建官能化烯胺酮或杂环化合物的一种更为原子和步骤经济的策略, 并引起了许多有机化学家的关注. 根据成键类型, 该综述分为五个部分: C-C键的形成、C-O键的形成、C-N键的形成和C-X键的形成以及C-S/C-Se键的形成. 主要对烯胺酮α位官能团化反应进行了综述, 从反应机理、反应体系、底物范围等角度系统地综述了烯胺酮α位官能团化反应的进展.

关键词: 烯胺酮, 官能团化, 偶联反应, 高价碘

Enaminones are versatile and extremely useful building blocks in organic synthesis with the advantages of easy availability, convenient storage, and distinct reactivity. In particular, such compounds are important precursors in heterocyclic chemistry. Recently, transition-metal-catalyzed or transition-metal-free α-functionalization of enaminones by C-H activation has emerged as a more atom- and step-economical strategy for the construction of functionalized enaminones or various heterocycles, and it has attracted the attention of many organic chemists. This review is divided into five sections based on the varied chemical bonds: C-C bond formation, C-O bond formation, C-N bond formation, C-X bond formation, and C-S/Se bond formation. The recent progress in functionalization of enaminone based on the reaction mechanism, reaction system, the scope of substrates, etc. is systematically reviewed.

Key words: enaminone, functionalization, coupling reaction, hypervalent iodine

引用此文

刘宁, 爨晓丹, 李慧, 段希焱. 烯胺酮α-官能团化反应的研究进展[J]. 有机化学, 2023, 43(2): 602-621.

Ning Liu, Xiaodan Cuan, Hui Li, Xiyan Duan. Progress in the Study of α-Functionalization of Enaminone[J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 602-621.

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图/表 39

图式1. 常见的烯胺酮的结构以及应用

Scheme 1. General structure and application of enaminones

图式2. 环烯胺酮的脱氢烯基化反应

Scheme 2. Dehydrogenative alkenylation reaction of cyclic enaminones

图式3. 邻羟苯基烯胺酮与烯烃反应合成3-烯基色酮

Scheme 3. Synthesis of 3-vinyl chromones via the reactions between o-hydroxyphenyl enaminones and alkenes

图式4. 钯催化下烯胺酮与烯烃C(sp2)-H活化反应合成吡咯

Scheme 4. Palladium-catalyzed C(sp2)-H activation with enaminones and alkenes for pyrrole synthesis

图式5. 邻羟基苯基叔烯胺酮和溴卞的环化苄基化反应

Scheme 5. Cyclobenzylation of o-hydroxyarylenaminones with benzyl bromide

图式6. 金催化下邻羟基芳基烯胺酮的炔基化/环化反应

Scheme 6. Gold-catalyzed alkynylation/cyclization of o-hydr- oxyarylenaminones

图式7. N-芳基烯胺酮的氧化环化反应

Scheme 7. Oxidative cyclization of N-aryl enaminones

图式8. 钯催化N-芳基烯胺酮的氧化环化反应

Scheme 8. Palladium-catalyzed oxidative cyclization of N-aryl enaminones

图式9. PIDA催化N-芳基烯胺酮的氧化环化反应

Scheme 9. PIDA catalyzed oxidative cyclization of N-aryl enaminones

图式10. 钯催化的叔胺氧化环化反应

Scheme 10. Palladium-catalyzed oxidative cyclization of tertiary enamines

图式11. 邻羟基苯基烯胺酮与芳基硼酸瞬态可循环卤化偶联

Scheme 11. Transient and recyclable halogenation coupling of o-hydroxyphenyl enaminones and aryl boronic acids

图式12. 钯催化的烯胺酮的芳基化反应

Scheme 12. Palladium(II)-catalyzed direct arylation of enaminones

图式13. 烯胺酮与异腈的周环反应

Scheme 13. Cyclic reaction of enamine and nitrile

图式14. 钯催化的(Z)-烯胺化合物和异腈化合物的氧化偶联反应

Scheme 14. Palladium-catalyzed oxidative coupling reactions of (Z)-enamines with isocyanides

图式15. 烯胺酮与三氟甲基磺酸钠的三氟甲基化反应

Scheme 15. Trifluoromethylation of enaminones with trifluoromethane sulfinate

图式16. 可见光驱使的烯胺酮三氟甲基化反应

Scheme 16. Visible-light-driven trifluoromethylation of enaminones

图式17. Togni试剂介导的烯胺酮三氟甲基化反应

Scheme 17. Togni reagent-mediated trifluoromethylation of enaminone

图式18. 烯胺酮的C-H三氟甲基化和色酮环化

Scheme 18. C-H Trifluoromethylation and chromone annulation of enaminones

图式19. 亚碘酰苯催化下的烯胺酮与羧酸的C-O偶联反应

Scheme 19. C-O coupling reaction of enamines and carboxylic acid catalyzed by PhIO

图式20. 非金属条件下叔烯胺酮的高位点选择性C-H酰基化反应

Scheme 20. Highly site-selective metal-free C-H acyloxylation of tertiary enaminones

图式21. 叔烯胺酮的热引发自由基C-H酰化反应

Scheme 21. Thermoinduced free-radical C-H acyloxylation of tertiary enaminones

图式22. 亚碘酰苯介导的烯胺化合物三氟乙氧化和氮杂丙烯啶化反应

Scheme 22. PhIO-mediated trifluoroethoxylation and azirination of enamines

图式23. 烯胺酮和缺电子胺的直接氧化偶联

Scheme 23. Direct oxidative coupling of enaminone and electron-deficient amines

图式24. 高价碘介导的烯胺酮与炔胺的氧化交叉偶联反应

Scheme 24. Iodine(III)-mediated oxidative cross-coupling of enaminone and propargylamines

图式25. 烯胺酮的氮杂环芳化生成C2-氮化色酮

Scheme 25. Toward C2-nitrogenated chromones by N-hetero- arylation of enaminones

图式26. NBS促进的烯胺酮C-H胺化反应

Scheme 26. NBS-promoted C-H amination of enaminones

图式27. 烯胺酮的氮杂环芳化生成C2-氮化色酮

Scheme 27. Toward C2-nitrogenated chromones by N-heteroarylation of enaminones

图式28. 叔烯胺酮的卤化反应

Scheme 28. Halogenation of tertiary enaminone

图式29. 烯胺酮的氟化反应

Scheme 29. Fluorination of enaminone

图式30. 以卤化钠(NaX)为卤素源的烯胺类电化学C-H卤化反应

Scheme 30. Electrochemical C-H halogenations of enaminones with sodium halide (NaX) as halogen source

图式31. KIO3催化下烯胺酮的硫醇化反应

Scheme 31. KIO3 catalyzed thiolation reaction of enaminones

图式32. 叔烯胺酮与β-氨基硫醇反应合成二硫取代的烯胺酮和1,4-噻嗪

Scheme 32. Synthesis of disulfide-functionalized enaminones and 1,4-thiazines via the reactions of enaminones and β-amino- ethanethiol

图式33. 烯胺酮与β-氨基硫醇反应合成二硫取代的烯胺酮和1,4-噻嗪

Scheme 33. Synthesis of disulfide-functionalized enaminones and 1,4-thiazines via the reactions of enaminones and β-aminoethanethiol

图式34. 通过烯胺酮的多米诺C-H磺酰化反应合成吡咯

Scheme 34. Synthesis of pyrazole by domino C-H sulfonylation of enaminones

图式35. K2S2O8为氧化剂烯胺酮的硫氰化

Scheme 35. K2S2O8 oxidized the thiocyanation of enaminone

图式36. 以PIDA为介导烯胺酮的硫氰化

Scheme 36. PIDA mediated the thiocyanation of enaminone

图式37. 光催化的烯胺酮的硫氰化

Scheme 37. Visible light-induced thiocyanation of enaminone

图式38. NBS促进烯胺酮的硫氰基化

Scheme 38. NBS promoted the thiocyanation of enaminone

图式39. 铜催化硫氰酸酯与末端炔烃的硫炔基化反应

Scheme 39. Copper-catalyzed thioalkynylation of thiocyanates with terminal alkynes

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