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Aerobic oxidation of benzylic alcohols with bis(3,5-di-tert-butylsalicylaldimine)copper(II) complexes

Paper ID Volume ID Publish Year Pages File Format Full-Text
42380 45923 2009 5 PDF Available
Title
Aerobic oxidation of benzylic alcohols with bis(3,5-di-tert-butylsalicylaldimine)copper(II) complexes
Abstract

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 °C and 1 bar of O2 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 °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.

Graphical abstractA catalytic procedure for aerobic oxidation of alcohols was developed by utilizing bis(3,5-di-tert-butylsalicylaldimine)copper(II) complexes. The use of molecular oxygen as an ultimate stoichiometric oxidant, low loading of both TEMPO and copper catalyst make the system attractive candidate for sustainable oxidation of benzylic alcohols. Under optimal conditions, various alcohols could be selectively transformed into their corresponding aldehydes in excellent conversions.Figure optionsDownload full-size imageDownload high-quality image (49 K)Download as PowerPoint slide

Keywords
Aerobic oxidation; Alcohols; TEMPO; Copper(II) complexes; Salicylaldimine
First Page Preview
Aerobic oxidation of benzylic alcohols with bis(3,5-di-tert-butylsalicylaldimine)copper(II) complexes
Publisher
Database: Elsevier - ScienceDirect
Journal: Applied Catalysis A: General - Volume 371, Issues 1–2, 15 December 2009, Pages 17–21
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Catalysis