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Lang, Xianjun; Zhao, Jincai; Chen, Xiaodong
Angewandte Chemie (International ed.), April 4, 2016, Volume: 55, Issue: 15Journal Article
TiO2 photoredox catalysis has recently attracted much interest for use in performing challenging organic transformations under mild reaction conditions. However, the reaction scheme is hampered by the fact that TiO2 can only be excited by UV light of wavelengths λ shorter than 385 nm. One promising strategy to overcome this issue is to anchor an organic, preferably metal‐free dye onto the surface of TiO2. Importantly, we observed that the introduction of a catalytic amount of the redox mediator TEMPO (2,2,6,6‐tetramethylpiperidin‐1‐yl)oxyl ensured the stability of the anchored dye, alizarin red S, thereby resulting in the selective oxidation of organic sulfides with O2. This result affirms the essential role of the redox mediator in enabling the organic transformations by visible‐light photoredox catalysis. Dye‐sensitized titanium dioxide and a catalytic amount of the redox mediator TEMPO, (2,2,6,6‐tetramethylpiperidin‐1‐yl)oxyl, served as a well‐organized scheme of photoredox catalysis for the selective oxidation of sulfides into sulfoxides using oxygen under irradiation of visible light. The redox mediator enabled the organic transformations by visible‐light‐induced photoredox catalysis.
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