Synthesis, Immobilization and Catalytic Activity of a CopperII Complex with a Chiral BisoxazolineReport as inadecuate


Synthesis, Immobilization and Catalytic Activity of a CopperII Complex with a Chiral Bisoxazoline


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1

Department of Chemistry, CICECO, University of Aveiro, Aveiro 3810-193, Portugal

2

Departamento de Física de Polímeros, Elastámeros y Applicaciones Energéticas, Instituto de Ciencia e Tecnología de Polímeros, CSIC, Madrid 28006, Spain

3

Green Chemistry Centre of Excellence, Department of Chemistry, University of York, York YO10 5DD, UK





*

Author to whom correspondence should be addressed.



Abstract A chiral bisoxazoline bearing CH2OH groups was synthesized from a commercial bisoxazoline and characterized by 1H- and 13C-NMR, high resolution ESI-mass spectrometry and FTIR. The corresponding copperII complex was immobilized onto the surface of a mesoporous carbonaceous material Starbon® 700 in which the double bonds had been activated via conventional bromination. The materials were characterized by elemental analysis, ICP-OES, XPS, thermogravimetry and nitrogen adsorption at 77 K. The new copperII bisoxazoline was tested both in the homogeneous phase and once immobilized onto a carbonaceous support for the kinetic resolution of hydrobenzoin. Both were active, enantioselective and selective in the mono-benzoylation of hydrobenzoin, but better enantioselectivities were obtained in the homogeneous phase. The heterogeneous catalyst could be separated from the reaction media at the end of the reaction and reused in another catalytic cycle, but with loss of product yield and enantioselectivity. View Full-Text

Keywords: copperII; bisoxazoline; homogeneous catalysis; heterogeneous catalysis; asymmetric catalysis copperII; bisoxazoline; homogeneous catalysis; heterogeneous catalysis; asymmetric catalysis





Author: Liliana Carneiro 1, Ana R. Silva 1,* , Peter S. Shuttleworth 2, Vitaly Budarin 3 and James H. Clark 3

Source: http://mdpi.com/



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