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Issue 1, 2018
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Effects of appended hydroxyl groups and ligand chain length on copper coordination and oxidation activity

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Abstract

Treatment of a series of (imino)pyridine ligands bearing appended hydroxyl groups 2-((pyridin-2-ylmethylene)amino)phenol (Hpyph), 2-((pyridin-2-ylmethylene)amino)ethanol (Hpyet), and 3-((pyridin-2-ylmethylene)amino)propanol (Hpypr) with one equiv. of CuCl2·2H2O afforded the corresponding Cu(II) complexes in low to moderate yields. The crystal structure of (μ-Cl)2[CuCl(κ2-N,N-Hpyet)]2 reveals a symmetric dinuclear structure with the bidentate N,N-coordination mode of (imino)pyridine with no Cu–OH interaction. On the other hand, the dinuclear Cu(II) complex of the related propyl ligand Hpypr possesses a significantly different crystal structure involving nucleophilic addition of the hydroxyl group to the aldehyde group of 2-pyridinecarboxaldehyde. The Cu complex/Cu0/TEMPO/Na2CO3 (TEMPO = 2,2,6,6-tetramethylpiperidinyl-1-oxyl) catalyst system generally exhibited good activity for aerobic oxidation of benzyl alcohol to benzaldehyde in H2O at room temperature. The dinuclear Cu(II) complex (μ-Cl)2[CuCl(κ2-N,N-Hpyet)]2 was demonstrated as an effective catalyst toward aerobic oxidation of various benzyl alcohol derivatives, cinnamyl alcohol, and 2-thiophenemethanol.

Graphical abstract: Effects of appended hydroxyl groups and ligand chain length on copper coordination and oxidation activity

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Publication details

The article was received on 20 Aug 2017, accepted on 28 Nov 2017 and first published on 28 Nov 2017


Article type: Paper
DOI: 10.1039/C7NJ03113K
Citation: New J. Chem., 2018,42, 654-661
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    Effects of appended hydroxyl groups and ligand chain length on copper coordination and oxidation activity

    A. Jehdaramarn, S. Pornsuwan, P. Chumsaeng, K. Phomphrai and P. Sangtrirutnugul, New J. Chem., 2018, 42, 654
    DOI: 10.1039/C7NJ03113K

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