2006/11/11 by Joseph M. Grill, J. W. Ogle, Stephen A. Miller · 1 citation
Chemistry · Materials Science · #Chemical Synthesis and Reactions #Mesoporous Materials and Catalysis #Oxidative Organic Chemistry Reactions
paper · doi:10.1021/jo0612574
openalex publication_date 2006/11/11 · openalex created_date 2016/06/24 · openalex updated_date 2026/06/26
Upon exposure to commercial bleach (approximately 5% aqueous sodium hypochlorite), nickel(II) chloride or nickel(II) acetate is transformed quantitatively into an insoluble nickel species, nickel oxide hydroxide. This material consists of high surface area nanoparticles (ca. 4 nm) and is a useful heterogeneous catalyst for the oxidation of many organic compounds. The oxidation of primary alcohols to carboxylic acids, secondary alcohols to ketones, aldehydes to carboxylic acids, and alpha, beta-unsaturated carboxylic acids to epoxy acids is demonstrated using 2.5 mol % of nickel catalyst and commercial bleach as the terminal oxidant. We demonstrate the controlled and selective oxidation of several organic substrates using this system affording 70-95% isolated yields and 90-100% purity. In most cases, the oxidations can be performed without an organic solvent, making this approach attractive as a "greener" alternative to conventional oxidations.