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Molecules 2009, 14(8), 3019-3029; doi:10.3390/molecules14083019
Article

Coupling Reactions of α-Bromocarboxylate with Non-Aromatic N-Heterocycles

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Received: 20 July 2009 / Revised: 30 July 2009 / Accepted: 12 August 2009 / Published: 13 August 2009
(This article belongs to the Special Issue Heck Coupling)
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Abstract

The conditions for the C-N bond forming reaction (C-N coupling reaction) between α-bromocarboxylate and nitrogen-containing non-aromatic heterocyclic rings under heterogeneous copper(I) oxide catalysis are investigated in this paper. All the generated compounds were fully characterized by IR, NMR and MS spectroscopy. Ab initio/DFT calculations of partial charges on nitrogen atoms in all the discussed heterocycles and on C(2) of carboxylate under applied conditions were predicted. These in silico results correlate relatively with the experimental observations.
Keywords: C-N nucleophilic coupling; N-heterocycles; ω-lactams; copper catalyst; ab initio/DFT calculations C-N nucleophilic coupling; N-heterocycles; ω-lactams; copper catalyst; ab initio/DFT calculations
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Brychtova, K.; Slaba, B.; Placek, L.; Jampilek, J.; Raich, I.; Csollei, J. Coupling Reactions of α-Bromocarboxylate with Non-Aromatic N-Heterocycles. Molecules 2009, 14, 3019-3029.

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