Functionalization of saturated hydrocarbons. Part 4. The Gif system for selective oxidation using molecular oxygen

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Abstract
Various systems for the selective oxidation of saturated hydrocarbons have been developed. These are based on the idea of an iron catalyst which is reduced by electron transfer and oxidized by molecular oxygen simultaneously in the presence of a source of protons. Four modifications of this system (the Gif system) have been devised of which the best (Gif IV) consists of an iron catalyst with metallic zinc as the reductant, acetic acid as the proton source and pyridine as the solvent. At room temperature, using oxygen or air saturated hydrocarbons are oxidized selectively to ketones in isolated yields superior to those reported for comparable model systems.