Homogeneous oxidation of alcohol and alkene with copper (II) complex in water

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Abstract

A new water-soluble copper(II) complex bearing 4-bromobenzoate/2,2’-dipyridylamine ligands was successfully synthesized and characterized by using single crystal X-ray diffraction and spectroscopic techniques. The catalytic activity of the compound was investigated as a homogeneous catalyst in the oxidation of several alcohols (benzyl alcohol, cinnamyl alcohol, 1-phenylethanol, cyclohexanol, 1-heptanol) and alkenes (styrene, ethylbenzene, cyclohexene) in aqueous medium. The copper(II) catalyst was found to be active for the studied alcohols and alkenes. \(\hbox {H}_{2}\hbox {O}_{2}\) was used as an active oxidant for alcohol oxidation, while t-BuOOH (TBHP) was used for alkenes. The compound exhibited high selectivity toward benzaldehyde (88%) in cinnamyl alcohol oxidation under mild conditions (70 \({^{\circ }}\hbox {C}\)) after 4 h. Particularly, remarkable results were obtained for the oxidation of styrene and cyclohexene; transformation via allylic oxidation to 2-cyclohexene-1-one as one product in 2 h \((\hbox {TOF} = 50\,\hbox {h}^{-1})\) and benzaldehyde in 1 h (100% conversion, TOF = 86 \(\hbox {h}^{-1}\), 100% selectivity). The Cu(II)/TBHP (or \(\hbox {H}_{2}\hbox {O}_{2})/\hbox {H}_{2}\hbox {O}\) system proved to be an alternative for catalytic oxidations in the green chemistry concept.

Graphical Abstract

New Copper(II)-complex bearing 4-bromobenzoate/2,2’-dipyridylamine ligands was synthesized and characterized by single crystal diffraction technique. The complex exhibited good catalytic oxidation activity on alcohols and alkenes in water, a green solvent.

Keywords

Copper (II) complex oxidation alcohol alkene 

Notes

Acknowledgements

Authors thankfully acknowledge the Medical Plants and Medicine Research Centre of Anadolu University, Eskişehir, Turkey for using X-ray Diffractometer.

Supplementary material

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Supplementary material 1 (docx 17 KB)
12039_2018_1439_MOESM2_ESM.pdf (148 kb)
Supplementary material 2 (pdf 147 KB)
12039_2018_1439_MOESM3_ESM.pdf (245 kb)
Supplementary material 3 (pdf 245 KB)

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Copyright information

© Indian Academy of Sciences 2018

Authors and Affiliations

  1. 1.Department of Chemistry, Faculty of ScienceAnadolu UniversityEskisehirTurkey

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