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Issue 32, 2014
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Synthesis and characterization of new chiral Cu(ii)–N4 complexes and their application in the asymmetric aza-Henry reaction

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Abstract

Cu(II) Schiff base complexes Cu(II)-1 and Cu(II)-3 based on 2-acetyl pyridine with both (1R,2R)-1,2-diaminocyclohexane and (1S,2S)-1,2-diaminocyclohexane were synthesized in a single step. Subsequent reduction of ligands 1 and 3 with NaBH4 followed by complexation with Cu(OTf)2 resulted in generation of two more additional chiral centers in complexes Cu(II)-2 and Cu(II)-4. The ligands 1–4 and their corresponding complexes were well characterized by several spectral techniques like 1H-NMR, 13C-NMR, LC-MS, CD, UV-Vis spectroscopy and microanalysis. The respective Cu(II) complexes derived from ligands 2 and 4 were investigated using both the solution and solid state EPR spectra. The particular orientation of the reduced complex with Cu(OTf)2 was confirmed by the X-ray crystal structure of the corresponding complex. All the catalytic protocols were applied in the asymmetric aza-Henry reaction to evaluate the catalytic properties of the Cu(II) complexes in the present study.

Graphical abstract: Synthesis and characterization of new chiral Cu(ii)–N4 complexes and their application in the asymmetric aza-Henry reaction

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Supplementary files

Article information


Submitted
24 Apr 2014
Accepted
18 Jun 2014
First published
19 Jun 2014

Dalton Trans., 2014,43, 12357-12364
Article type
Paper

Synthesis and characterization of new chiral Cu(II)–N4 complexes and their application in the asymmetric aza-Henry reaction

A. Das, R. I. Kureshy, N. Ch. Maity, P. S. Subramanian, N. H. Khan, S. H. R. Abdi, E. Suresh and H. C. Bajaj, Dalton Trans., 2014, 43, 12357
DOI: 10.1039/C4DT01202J

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