Iron-catalyzed olefin cis-dihydroxylation by H2O2: Electrophilic versus nucleophilic mechanisms

Megumi Fujita, Miquel Costas, Lawrence Que

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Abstract

Previous studies have classified a series of nonheme iron catalysts for olefin cis-dihydroxylation by H2O2 into two groups. Complex 1, [(TPA)Fe(OTf)2], representative of Class A catalysts, forms a low-spin FeIII-OOH intermediate that gives rise to a high-valent FeV(=O)OH oxidant. The preference of this catalyst for electron-rich olefins demonstrates its electrophilic character. On the other hand, complex 2, [(6-Me3-TPA)Fe(OTf)2], representative of Class B catalysts, prefers instead to oxidize electron-deficient olefins, suggesting an oxidant with nucleophilic character. It is suggested that such a nucleophilic oxidant may be the high-spin FeIII-OOH intermediate derived from 2 or the FeIV(=O)(•OH) species derived therefrom.

Original languageEnglish (US)
Pages (from-to)9912-9913
Number of pages2
JournalJournal of the American Chemical Society
Volume125
Issue number33
DOIs
StatePublished - Aug 20 2003

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