Recent Advances of the Synthesis of Indolines by Unactivated Alkenes

doi:10.6023/cjoc201904014

Abstract

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

Cite this article

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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Fig. & Tab. 18

Figure 1. Indoline nucleus

Figure 2. Representative natural alkaloids with the indoline framework

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

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

Scheme 3. Copper-catalyzed trifluoromethylation of unactivated alkenes

Scheme 4. Trifluoroalkylation of TFAA with N-arylallylamine

Scheme 5. Polyfluoroalkylation of Umemoto and unactivated alkenes

Scheme 6. Palladium-catalyzed aryl perfluoroalkylation of unactivated alkenes

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

Scheme 8. Palladium-catalyzed oxidative arylalkylation of unactivated alkenes

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

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

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

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

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

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

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

Scheme 16. Silver-Catalyzed radical arylphosphorylation of unactivated alkenes

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