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Synthesis of anti‐Markovnikov Alcohols via Epoxidation and Hydrogenation of Styrenes using Photocatalytically Generated Redox Equivalents
Author(s) -
Graml Andreas,
König Burkhard
Publication year - 2021
Publication title -
chemphotochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.13
H-Index - 18
ISSN - 2367-0932
DOI - 10.1002/cptc.202000205
Subject(s) - markovnikov's rule , photocatalysis , chemistry , catalysis , hydrogen peroxide , redox , regioselectivity , epoxide , titanium dioxide , photochemistry , styrene , vinyl ether , oxygen , organic chemistry , combinatorial chemistry , materials science , polymer , copolymer , metallurgy
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.