CHEN Wei, WANG Peilong, SUN Yue, SU Yiming, ZHENG Xiaoqi*
(Department of Chemistry, University of Science and Technology of China, Hefei 230026, P. R. China)
Abstract: Ni(OAc)2 combined with pyridine and tert-Butylhydroperoxide (TBHP) affords selective catalytic aerobic oxidations of benzylic C-Hs and alcohols under mild conditions (80-90℃, O2 1 atm). The effects of ligand, solvent, temperature and the nature of the peroxide additives were investigated to give an optimised oxidation protocol for these compounds. In the oxidation of the benzylic C-Hs, a high ketone/ alcohol selectivity were obtained. Ni(III) was detected by ESR, and the mechanism was verified. Competition experiments revealed that formation of the carbonyl compounds is not a result of further oxidation of the alcohols. It is suggested that ketone are a product of metal-catalysed decomposition of the hydroperoxide.
Key words: molecular oxygen; oxidation/ nickel catalysis; alcohol; C-H functionalization
E-mail: xqzheng@ustc.edu.cn
Journal of Molecular Catalysis, Vol. 26, Issue 1, 2012, 19-25
