Synthesis, Immobilization and Catalytic Activity of a Copper(II) Complex with a Chiral Bis(oxazoline)
authors Carneiro, L; Silva, AR; Shuttleworth, PS; Budarin, V; Clark, JH
nationality International
journal MOLECULES
author keywords copper(II); bis(oxazoline); homogeneous catalysis; heterogeneous catalysis; asymmetric catalysis
keywords HETEROGENEOUS CATALYSTS; ACTIVATED CARBON; ENANTIOSELECTIVE CATALYSIS; ASYMMETRIC BENZOYLATION; MESOPOROUS SILICAS; CYCLOPROPANATION; EPOXIDATION; AZA-BIS(OXAZOLINE); MICROWAVE; REPLICAS
abstract A chiral bis(oxazoline) bearing CH2OH groups was synthesized from a commercial bis(oxazoline) and characterized by H-1- and C-13-NMR, high resolution ESI-mass spectrometry and FTIR. The corresponding copper(II) complex was immobilized onto the surface of a mesoporous carbonaceous material (Starbon (R) 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 copper(II) bis(oxazoline) 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.
publisher MDPI AG
issn 1420-3049
year published 2014
volume 19
issue 8
beginning page 11988
ending page 11998
digital object identifier (doi) 10.3390/molecules190811988
web of science category Chemistry, Organic
subject category Chemistry
unique article identifier WOS:000341502600072
link 25116806
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journal impact factor 3.098
5 year journal impact factor 3.268
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