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Published on: May 21, 2019
Redox-innocent scandium(III) as the sole catalyst in visible light photooxidations
Amal Hassan Tolba1,2, Ahmed M El-Zohry3, Jafar Iqbal Khan4
1Department of Organic Chemistry, University of Chemistry and Technology, Prague, Prague, 166 28, Czech Republic. amal.hassan44@yahoo.com.
Abstract:
In recent years, the catalytic activity of scandium triflate Sc(OTf)3 has attracted significant attention due to its robust Lewis acidity and the oxophilicity of Sc3+. These features have led to impressive progress in developing diverse organic reactions, including C-C bond formation. The Sc3+ also facilitates single electron transfer in photoinduced reactions either by coordination to an organophotoredox catalyst, which modifies its redox reactivity, or by the formation of a scandium-superoxide anion complex after electron transfer from a light-absorbing redox-active compound. The prior consideration of Sc3+ as a redox-inactive/innocent metal ion initially hampered the investigation of the possibility of using Sc(OTf)3 as a sole visible light photoredox catalyst. This work demonstrates the use of Sc(OTf)3 as a visible light photocatalyst capable of direct and mild aerobic oxidative C-H functionalisation of aromatic substrates by oxidation of the benzylic position and direct cyanation of the aromatic ring.
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