A Sustainable C-H Activation of Indoles, Pyrroles and Furans with Blue LED and Iodine Ylides and Its Application in the Synthesis of Azepin[4, 5-B]Indoles

Social Science Research Network(2021)

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For the first-time pyrrole and indole derivatives are functionalized with dimethylmalonate derived phenyl iodonium ylide 4a in presence of blue LED via C-H activation of the respective heterocycles to generate the desired compounds 5 - 7 in moderate to good yields. Control experiments and density functional theory calculations provide insight into the probable reaction mechanism. Iodine ylides derived from 2, 4-dinitrophenyl acetate was generated in situ to provide alkylated pyrrole 5m. Finally the strategy is successfully applied in the generation of azepino[4, 5-b]indole 14a.
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Key words
indoles,synthesis,iodine ylides
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