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(Green) Photocatalytic Synthesis Employing Nitroaromatic Compounds

Published online by Cambridge University Press:  17 May 2011

Ralf Dillert
Affiliation:
Institut für Technische Chemie, Gottfried Wilhelm Leibniz Universität, Callinstrasse 3, 30167 Hannover, Germany
Amer Hakki
Affiliation:
Institut für Technische Chemie, Gottfried Wilhelm Leibniz Universität, Callinstrasse 3, 30167 Hannover, Germany
Detlef W. Bahnemann
Affiliation:
Institut für Technische Chemie, Gottfried Wilhelm Leibniz Universität, Callinstrasse 3, 30167 Hannover, Germany
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Abstract

The combination of a solid photocatalyst (TiO2) and a co-catalyst (p-toluenesulfonic acid) has been successfully applied for the light-induced conversion of nitroarenes in O2-free ethanolic suspensions yielding substituted quinolines and tetrahydroquinolines, while in the presence of TiO2 loaded with a noble metal (Pt, Pd) N-alkylarylamines and N,N-dialkylarylamines were formed. Depending on the compounds that have been detected by GC–MS the reaction mecha-nism is discussed comprising the formation of anilines and ethanal by a photocatalytic reaction step and their subsequent thermal reactions to quinolines, tetrahydroquinolines, and N-alkylated anilines via a Schiff base as an intermediate product.

Type
Research Article
Copyright
Copyright © Materials Research Society 2011

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