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

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...

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Bibliographic Details
Published in:New journal of chemistry 2018, Vol.42 (9), p.6880-6888
Main Authors: Hosseini-Sarvari, Mona, Koohgard, Mehdi, Firoozi, Somayeh, Mohajeri, Afshan, Tavakolian, Hosein
Format: Article
Language:English
Subjects:
Alizarin
Ambient temperature
Bonding
Cascade chemical reactions
Chemical reactions
Hydrogen bonds
Light irradiation
Titanium dioxide
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Summary: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.
ISSN:1144-0546
1369-9261
DOI:10.1039/c8nj00476e