Journal
APPLIED CATALYSIS A-GENERAL
Volume 371, Issue 1-2, Pages 17-21Publisher
ELSEVIER SCIENCE BV
DOI: 10.1016/j.apcata.2009.09.011
Keywords
Aerobic oxidation; Alcohols; TEMPO; Copper(II) complexes; Salicylaldimine
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A series of bis(3,5-di-tert-butylsalicylaldimine)copper(II) complexes were synthesized and employed in the catalytic oxidation of alcohols using molecular oxygen as a terminal oxidant. These complexes, when combined with TEMPO form a highly efficient catalytic system for the aerobic oxidation of primary benzylic and allylic alcohols under mild reaction conditions. For example at 60 degrees C and 1 bar of O-2 pressure benzyl alcohol is quantitatively converted to benzyl aldehyde in 2 h with low catalyst loading. Attractive features of this catalytic system include the efficient use of molecular oxygen, high selectivity, low loading of both TEMPO (2 mol%) and copper catalyst (0.66 mol%) and mild reaction conditions (atmospheric oxygen and 60 degrees C temperature). In addition, the crystal structure of the complex was determined by X-ray diffraction analysis. The structure presents the Cu ion in a monomeric distorted square-planar geometry involving the unusual and sterically unfavorable cis-N2O2 coordination sphere. (C) 2009 Elsevier B.V. All rights reserved.
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