Access to Functionalized Quinones via the Aromatic Oxidation of Phenols Bearing an Alcohol or Olefinic Function Catalyzed by Supported Iron Phthalocyanine
New Journal of Chemistry
, E-ISSN: 1369-9261
Zalomaeva Olga V.
Sorokin Alexander B.
Institute of Researches on Catalysis and Environment in Lyon
Boreskov Institute of Catalysis SB RAS
The controlled oxidation at only one position of compounds with several oxidizable sites, while keeping the other sites intact, has been demonstrated for phenols bearing alcohol or olefinic functional groups. Iron tetrasulfophthalocyanine supported on silica was found to be an efficient catalyst for the preparation of functionalized quinones under mild conditions, with tert-butylhydroperoxide as the oxidant. A novel rapid and mild one-pot procedure for the covalent grafting of iron tetrasulfophthalocyanine onto silica has been developed. The supported catalyst was characterized by chemical analysis, a specific surface study, UV-vis spectroscopy and XPS. A non-radical mechanism for this unusual selective oxidation has been revealed by 18O labelling experiments.