Selective Oxidation of Benzylic Alcohols to the Corresponding Aldehydes or Ketones with Perster in the Presence of CuPF6 as a Catalyst

Document Type : Research Article

Authors

1 Department of Chemistry, Faculty of Science, Babol Noshirvani University of Technology, Babol, I.R. IRAN

2 Department of Chemistry, Faculty of Science, University of Kurdistan, Sanandaj, I.R. IRAN

Abstract

The catalytic activity of CuPF6 has been studied for the selective oxidation of benzylic alcohols to the corresponding aldehydes using tert-butyl p-nitrobenzoperoxoate an oxidizing agent. This system showed excellent catalytic activity for the oxidation of benzylic alcohols to the corresponding aldehydes with high selectivity. The complete conversion of the benzylic alcohols to the corresponding aldehydes is achieved within a short reaction period at 40 °C. The catalytic performance is obtained to be dependent on the electronic and steric effects of the substituents present on the phenyl ring. Electron donating groups on the para and meta position of phenyl ring increase the efficiency and reduce the reaction time (electronic effects). Also, different types of groups, such as donor and withdraw, on the ortho position of phenyl ring reduce the reaction efficiency and increase reaction time (steric effects). The oxidation of 1-phenylethanol and 1-indanol to the corresponding ketones was performed using a tert-butyl p-nitrobenzoperoxoate in the presence of CuPF6 for 5 hours, with a yield of 15% and 23% respectively. Oxidation of non-benzylic alcohols could not be oxidized to the corresponding aldehydes or ketones even after 24 h. Thus, tert-butyl p-nitrobenzoperoxoate was found to act as a highly chemoselective oxidant for the oxidation of primary and secondary benzylic alcohols in the presence of CuPF6 as a catalyst.

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References

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