Hydroxylation of linear alkanes catalysed by iron porphyrins: particular efficacy and regioselectivity of perhalogenated porphyrins

Abstract

Iron porphyrins containing perhalogenated pyrroles are found to be much better catalysts for the hydroxylation of poorly reactive alkanes like pentane or heptane by PhIO (yields as high as 80%) than the corresponding iron porphyrins without halogens on the pyrrole rings; the chemoselectivity and regioselectivity of the oxidations are found to vary very much with the presence of pyrrole halogens suggesting a dramatic change in the structure of the oxygenating iron-oxo species.