基于未活化烯烃自由基加成/环化反应合成二氢吲哚类化合物的研究进展

doi:10.6023/cjoc201904014

摘要/Abstract

二氢吲哚是一类具有广泛生物学特性的重要杂环, 是许多天然产物和生物活性化合物的关键结构骨架. 有效的二氢吲哚合成方法已成为广泛研究的主题. 描述了利用未活化烯烃合成各种官能化二氢吲哚的最新研究, 其涉及在氧化剂存在下的自由基加成/环化反应, 这些反应通常用容易获得的氧化剂和不同的金属或非金属作为催化剂, 在中性条件下进行反应.

关键词: 二氢吲哚, 烯烃, 氧化剂, 官能团, 自由基

Indolines, an important class of heterocycles with a wide range of biological properties, are a key structural motif in numerous natural products and biologically active compounds. As a result, efficient methods for indolines synthesis have been the subject of extensive studies. In this review, recent studies on the synthesis of various functionalized indolines using unactivated alkenes are described. It involves radical addition/cyclization reaction in the presence of oxidizing agent, which is usually carried out under neutral reaction conditions using readily available oxidizing agents and different transition metals or under metal-free as catalysts.

Key words: indolines, alkenes, oxidizing agent, functional group, free radical

引用此文

刘颖杰, 林立青, 韩莹徽, 张鑫. 基于未活化烯烃自由基加成/环化反应合成二氢吲哚类化合物的研究进展[J]. 有机化学, 2019, 39(10): 2705-2712.

Liu Yingjie, Lin Liqing, Han Yinghui, Zhang Xin. Recent Advances of the Synthesis of Indolines by Unactivated Alkenes[J]. Chinese Journal of Organic Chemistry, 2019, 39(10): 2705-2712.

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图/表 18

图1. 二氢吲哚结构图

Figure 1. Indoline nucleus

图2. 具有二氢吲哚结构的代表性天然生物碱

Figure 2. Representative natural alkaloids with the indoline framework

图式1. 未活化的烯烃通过自由基加成/环化反应双官能化

Scheme 1. Difunctionalization of unactivated alkenes through radical addition/cyclization

图式2. 黄原酸酯和N-烯丙基对氟苯胺的多氟烷基化

Scheme 2. Polyfluoroalkylation of xanthate and N-allyl p-fluoroaniline

图式3. 铜催化的未活化烯烃的三氟甲基化

Scheme 3. Copper-catalyzed trifluoromethylation of unactivated alkenes

图式4. TFAA与N-芳基烯丙胺的三氟烷基化

Scheme 4. Trifluoroalkylation of TFAA with N-arylallylamine

图式5. Umemoto和未活化烯烃的多氟烷基化反应

Scheme 5. Polyfluoroalkylation of Umemoto and unactivated alkenes

图式6. 钯催化的未活化的烯烃的芳基全氟烷基化

Scheme 6. Palladium-catalyzed aryl perfluoroalkylation of unactivated alkenes

图式7. 未活化烯烃的分子内三氟甲基化/芳基化串联反应

Scheme 7. Intramolecular trifluoromethylation/arylation cascade reaction of unactiveted alkenes

图式8. 钯催化的未活化烯烃的氧化芳基烷基化

Scheme 8. Palladium-catalyzed oxidative arylalkylation of unactivated alkenes

图式9. 未活化烯烃和偶氮二异丁腈的自由基氰甲基化/芳基化反应

Scheme 9. Radical cyanomethylation/arylation reaction of unactivated alkenes with azobisisobutyronitrile

图式10. 无金属条件下未活化烯烃的自由基级联氯甲基化反应

Scheme 10. Metal-free radical cascade chloromethylation of unactivated alkenes

图式11. 未活化烯烃的自由基级联/氯甲基化反应的可能机制

Scheme 11. Possible mechanism for radical cascade chloromethylation of unactivated alkenes

图式12. 无金属条件下未活化烯烃与丙酮的氧化自由基级联加成反应

Scheme 12. Metal-free oxidative radical cascade addition reaction of unactivated alkenes with acetone

图式13. 串联环化-SRN1反应合成二氢吲哚

Scheme 13. Syntheses of indolines by tandem ring closure-SRN1 reactions

图式14. 黄原酸酯与未活化烯烃合成磷酰基化二氢吲哚

Scheme 14. Synthesis of phosphorylated indolin by xanthates and unactivated alkenes

图式15. Me3SnPPh 2进行芳基自由基磷酰化氧化得到二氢吲哚

Scheme 15. Indolin was obtained by aryl radical phosphorylation oxidation of Me3SnPPh2

图式16. 银催化的未活化烯烃的自由基芳基磷酸化

Scheme 16. Silver-Catalyzed radical arylphosphorylation of unactivated alkenes

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