NH3⋅H2O: The Simplest Nitrogen-Containing Ligand for Selective Aerobic Alcohol Oxidation to Aldehydes or Nitriles in Neat Water.

Abstract

Aqueous ammonia (NH3⋅H2O) has been shown to serve as the simplest nitrogen‐containing ligand to effectively promote copper‐catalyzed selective alcohol oxidation under air in water. A series of alcohols with varying electronic and steric properties were selectively oxidized to aldehydes with up to 95 % yield. Notably, by increasing the amount of aqueous ammonia in neat water, the exclusive formation of aryl nitriles was also accomplished with good‐to‐excellent yields. Additionally, the catalytic system exhibits a high level of functional group tolerance with −OH, −NO2, esters, and heteroaryl groups all being amenable to the reaction conditions. This one‐pot and green oxidation protocol provides an important synthetic route for the selective preparation of either aldehydes or nitriles from commercially available alcohols.