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Issue 10, 2014
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Synthesis, structure and catalytic applications of amidoterephthalate copper complexes in the diastereoselective Henry reaction in aqueous medium

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Abstract

Terephthalic acid derivatives bearing amide side functional groups, viz. 2-propionamidoterephthalic acid (H2L1) and 2-acetamidoterephthalic acid (H2L2), have been structurally characterized using X-ray crystallography. While H2L1 is hydrogen bonded with DMF molecules forming a 1D hydrogen bonded network, H2L2 constructs a 2D hydrogen bonded network. They have been used to synthesize two new isostructural mononuclear copper complexes, [Cu(L1)(H2O)4] (1) and [Cu(L2)(H2O)4] (2), also characterized using X-ray crystallography. In these structures the hydrogen bonded assemblies of carboxylate and coordinated water molecules form a distorted cubane type of hydrogen bonded network. Complexes 1 and 2 act as heterogeneous catalysts for the diastereoselective nitroaldol (Henry) reaction in aqueous medium, 1 providing high yields (up to 77%) and good diastereoselectivities under ambient conditions. These catalysts can be recycled without significant loss of activity, and the catalytic process is efficient, simple, easy to work-up and operates under ‘green’ conditions.

Graphical abstract: Synthesis, structure and catalytic applications of amidoterephthalate copper complexes in the diastereoselective Henry reaction in aqueous medium

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Publication details

The article was received on 29 May 2014, accepted on 14 Jul 2014 and first published on 29 Jul 2014


Article type: Paper
DOI: 10.1039/C4NJ00878B
Citation: New J. Chem., 2014,38, 4837-4846
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    Synthesis, structure and catalytic applications of amidoterephthalate copper complexes in the diastereoselective Henry reaction in aqueous medium

    A. Karmakar, S. Hazra, M. F. C. Guedes da Silva and A. J. L. Pombeiro, New J. Chem., 2014, 38, 4837
    DOI: 10.1039/C4NJ00878B

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