<p>In recent years, the catalytic activity of scandium triflate Sc(OTf)<sub>3</sub> has attracted significant attention due to its robust Lewis acidity and the oxophilicity of Sc<sup>3+</sup>. These features have led to impressive progress in developing diverse organic reactions, including C-C bond formation. The Sc<sup>3+</sup> 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 Sc<sup>3+</sup> as a redox-inactive/innocent metal ion initially hampered the investigation of the possibility of using Sc(OTf)<sub>3</sub> as a sole visible light photoredox catalyst. This work demonstrates the use of Sc(OTf)<sub>3</sub> 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.</p>

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Redox-innocent scandium(III) as the sole catalyst in visible light photooxidations

  • Amal Hassan Tolba,
  • Ahmed M. El-Zohry,
  • Jafar Iqbal Khan,
  • Eva Svobodová,
  • Josef Chudoba,
  • Jiří Klíma,
  • Karol Lušpai,
  • Martin Pižl,
  • Jiří Šturala,
  • Radek Cibulka

摘要

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.