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Access to functionalized quinones via the aromatic oxidation of phenols bearing an alcohol or olefinic function catalyzed by supported iron phthalocyanine

2006; Royal Society of Chemistry; Volume: 30; Issue: 12 Linguagem: Inglês

10.1039/b608834a

1369-9261

Olga V. Zalomaeva, Alexander B. Sorokin,

Metal-Catalyzed Oxygenation Mechanisms

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.