Publication: Effects of appended hydroxyl groups and ligand chain length on copper coordination and oxidation activity
Issued Date
2018-01-01
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ISSN
13699261
11440546
11440546
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2-s2.0-85038834316
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Mahidol University
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SCOPUS
Bibliographic Citation
New Journal of Chemistry. Vol.42, No.1 (2018), 654-661
Suggested Citation
Attawit Jehdaramarn, Soraya Pornsuwan, Phongnarin Chumsaeng, Khamphee Phomphrai, Preeyanuch Sangtrirutnugul Effects of appended hydroxyl groups and ligand chain length on copper coordination and oxidation activity. New Journal of Chemistry. Vol.42, No.1 (2018), 654-661. doi:10.1039/c7nj03113k Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/45450
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Title
Effects of appended hydroxyl groups and ligand chain length on copper coordination and oxidation activity
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Abstract
© 2018 The Royal Society of Chemistry and the Centre National de la Recherche Scientifique. 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.