Iron-Catalyzed Cyanide-Free Synthesis of Alkyl Nitriles: Oxidative Deconstruction of Cycloalkanones with Ammonium Salts and Aerobic Oxidation

A sustainable, cyanide-free synthesis of alkyl nitriles via the aerobic oxidative deconstruction of unstrained cycloalkanones with ammonium salts has been developed. Using inexpensive and stable ammonium salts as the nitrogen source, a variety of alkyl nitriles containing a distal carbonyl group were obtained in good yields under visible-light-promoted iron catalysis. This protocol is characterized by mild conditions, abundant and environmentally benign materials, and high atom and step economy with minimal waste generation. The primary mechanism study revealed that ¹O₂ is likely to be involved in this reaction.