Abstract
AbstractWe report an efficient method for a formal anti‐Markovnikov addition of water to styrenes through photocatalytic generation of redox equivalents, using a gold‐doped titanium dioxide (Au/TiO2) semiconductor as photocatalyst. Under irradiation with UV−A light, the photocatalytic activity of Au/TiO2 generates in situ under aerobic conditions hydrogen peroxide (H2O2) and under anaerobic conditions dihydrogen (H2). In the presence of oxygen and a Ru catalyst, the epoxidation of different styrene derivatives is achieved. Subsequently, regioselective reductive Pd‐catalyzed epoxide opening in the absence of oxygen gives the corresponding 2‐phenylethanol derivatives.
Highlights
TiO2-based semiconductor materials are used in photocatalytic processes, especially in applications for wastewater treatment and air purification.[1]
We show a photocatalytic alternative to classic synthetic strategies for 2-phenylethanol derivatives, which include Grignard reactions, Friedel-Crafts-type reactions, or biochemical approaches.[8]
Previous work has shown that Au/TiO2 is suitable for the photocatalytic generation of H2O2 as well as H2 from water or organic solvents.[9]
Summary
TiO2-based semiconductor materials are used in photocatalytic processes, especially in applications for wastewater treatment and air purification.[1] In most cases, hydrogen peroxide and hydroxyl radicals are produced by irradiation of TiO2 with light under aerobic conditions. Among others, these species are mainly responsible for the oxidative degradation of pollutants. TiO2 has attracted a lot of attention in photocatalytic energy production It is considered one of the most promising materials for hydrogen generation from oxidation of water under inert conditions.[2] In contrast, the use of TiO2 as photocatalyst for organic synthesis remains less explored with considerably fewer reports.[3]
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