Mechanistic Studies on the Hexadecafluorophthalocyanine–Iron‐Catalyzed Wacker‐Type Oxidation of Olefins to Ketones**
Florian Puls, F. Seewald, Vadim Grinenko, H.‐H. Klauß, Hans‐Joachim Knölker
Abstract
Abstract The hexadecafluorophthalocyanine–iron complex FePcF 16 was recently shown to convert olefins into ketones in the presence of stoichiometric amounts of triethylsilane in ethanol at room temperature under an oxygen atmosphere. Herein, we describe an extensive mechanistic investigation for the conversion of 2‐vinylnaphthalene into 2‐acetylnaphthalene as model reaction. A variety of studies including deuterium‐ and 18 O 2 ‐labeling experiments, ESI‐MS, and 57 Fe Mössbauer spectroscopy were performed to identify the intermediates involved in the catalytic cycle of the oxidation process. Finally, a detailed and well‐supported reaction mechanism for the FePcF 16 ‐catalyzed Wacker‐type oxidation is proposed.