Synthesis of anti‐Markovnikov Alcohols via Epoxidation and Hydrogenation of Styrenes using Photocatalytically Generated Redox Equivalents
Andreas Graml, Burkhard König
Abstract
Abstract We 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/TiO 2 ) semiconductor as photocatalyst. Under irradiation with UV−A light, the photocatalytic activity of Au/TiO 2 generates in situ under aerobic conditions hydrogen peroxide (H 2 O 2 ) and under anaerobic conditions dihydrogen (H 2 ). 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.
Topics & Concepts
Markovnikov's rulePhotocatalysisChemistryCatalysisHydrogen peroxideRedoxRegioselectivityEpoxideTitanium dioxidePhotochemistryStyreneVinyl etherOxygenOrganic chemistryCombinatorial chemistryMaterials scienceCopolymerMetallurgyPolymerAdvanced Photocatalysis TechniquesTiO2 Photocatalysis and Solar CellsAdvanced Nanomaterials in Catalysis