Journal article

Authors list: Becker, J; Gupta, P; Angersbach, F; Tuczek, F; Näther, C; Holthausen, MC; Schindler, S

Publication year: 2015

Pages: 11735-11744

Journal: Chemistry - A European Journal

Volume number: 21

Issue number: 33

ISSN: 0947-6539

DOI Link: https://doi.org/10.1002/chem.201501003

Publisher: Wiley

Abstract: 
The formation of a bis(μ-oxido)dicopper complex with the ligand 2-(diethylaminoethyl)-6-phenylpyridine (PPN) and its subsequent hydroxylation of the pendant phenyl group (studied earlier by Holland et al., Angew. Chem. Int. Ed.- 1999, 38, 1139-1142) has been reinvestigated to gain a better understanding of such systems in view of the development of new synthetic applications. To this end, we prepared a simple copper imine complex system that also affords selective o-hydroxylation of aromatic aldehydes by using dioxygen as the oxidant: Applying the ligand N'-benzylidene-N,N-diethylethylenediamine (BDED), salicylaldehyde was prepared in good yields and we show that this reaction also occurs through an intermediate bis-μ-oxido copper complex. The underlying reaction mechanism for the PPN-supported complex was studied at the BLYP-D/TZVP level of density functional theory and the results for representative stationary points along reaction paths of the BDED-supported complex reveal a closely related mechanistic scenario. The results demonstrate a new facile synthetic way to introduce OH groups into aromatic aldehydes.

Harvard Citation style: Becker, J., Gupta, P., Angersbach, F., Tuczek, F., Näther, C., Holthausen, M., et al. (2015) Selective Aromatic Hydroxylation with Dioxygen and Simple Copper Imine Complexes, Chemistry - A European Journal, 21(33), pp. 11735-11744. https://doi.org/10.1002/chem.201501003

APA Citation style: Becker, J., Gupta, P., Angersbach, F., Tuczek, F., Näther, C., Holthausen, M., & Schindler, S. (2015). Selective Aromatic Hydroxylation with Dioxygen and Simple Copper Imine Complexes. Chemistry - A European Journal. 21(33), 11735-11744. https://doi.org/10.1002/chem.201501003