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Issue 9, 2018
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Alizarin red S–TiO2-catalyzed cascade C(sp3)–H to C(sp2)–H bond formation/cyclization reactions toward tetrahydroquinoline derivatives under visible light irradiation

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Abstract

A very low amount of organic dye (Alizarin red S) sensitized TiO2 and it was successfully used to catalyze cascade C(sp3)–H to C(sp2)–H bond formation/cyclization reactions under visible light irradiation. The modified TiO2 photocatalyst efficiently, for the first time, advanced [4+2] cyclization of N,N-dimethylanilines and maleimides to the corresponding tetrahydroquinolines in air atmosphere. The reaction proceeds through α-amino radicals without additional oxidant at ambient temperature to afford products in good to excellent yields.

Graphical abstract: Alizarin red S–TiO2-catalyzed cascade C(sp3)–H to C(sp2)–H bond formation/cyclization reactions toward tetrahydroquinoline derivatives under visible light irradiation

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Publication details

The article was received on 27 Jan 2018, accepted on 22 Mar 2018 and first published on 24 Mar 2018


Article type: Paper
DOI: 10.1039/C8NJ00476E
Citation: New J. Chem., 2018,42, 6880-6888
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    Alizarin red S–TiO2-catalyzed cascade C(sp3)–H to C(sp2)–H bond formation/cyclization reactions toward tetrahydroquinoline derivatives under visible light irradiation

    M. Hosseini-Sarvari, M. Koohgard, S. Firoozi, A. Mohajeri and H. Tavakolian, New J. Chem., 2018, 42, 6880
    DOI: 10.1039/C8NJ00476E

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