Abstract
Iron(II) perchlorate in an H2O-H2O2-CH3CN mixture was used to efficiently carry out CH bond activations of benzene to form phenol and/or hydroquinone, and of toluene to form benzaldehyde, benzyl alcohol, o-cresol, p-cresol, and/or methyl-p-benzoquinone. The reactions were facilely tuned and controlled to selectively yield either a single or double oxygenation of benzene as well as a sp3 or sp2 CH bond oxidation of toluene. On the basis of H/D kinetic isotope effect data, we determined the aromatic oxidation to mostly proceed by way of formation of an arene oxide or a σ-complex intermediate from high-valence iron species and to then undergo a 1,2-hydride shift, i.e., NIH-shift rearrangement.
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