Heterogeneous photocatalysis of azides: extending nitrene photochemistry to longer wavelengths
Ignacio D. Lemir, Juan E. Argüello, Anabel E. Lanterna, J. C. Scaiano
Abstract
The photodecomposition of azides to generate nitrenes usually requires wavelengths in the <300 nm region. In this study, we show that this reaction can be readily performed in the UVA region (368 nm) when catalyzed by Pd-decorated TiO2. In aqueous medium the reaction leads to amines, with water acting as the H source; however, in non-protic and non-nucleophilic media, such as acetonitrile, nitrenes recombine to yield azo compounds, while azirine-mediated trapping occurs in the presence of nucleophiles. The heterogeneous process facilitates catalyst separation while showing great chemoselectivity and high yields.
Topics & Concepts
NitrenePhotochemistryPhotocatalysisAzideChemistryIrradiationWavelengthPhotodissociationPhotodegradationMaterials scienceOptoelectronicsCatalysisOrganic chemistryPhysicsNuclear physicsInnovative Microfluidic and Catalytic Techniques InnovationSynthesis and Catalytic ReactionsAdvanced Photocatalysis Techniques