3 years ago

Reactivity of Copper Complexes with Bis(piperidinyl)methane and Bis(quinolinyl)methane Ligands

Reactivity of Copper Complexes with Bis(piperidinyl)methane and Bis(quinolinyl)methane Ligands
Richard Göttlich, Jonathan Becker, Tim-Daniel J. Stumpf, Manfred Steinbach, Christian Würtele, Siegfried Schindler, Sabine Becker, Roland Fröhlich
Copper complexes with bis(piperidinyl)methane (BP) and bis(quinolinyl)methane (BQ) ligands were investigated. A dinuclear carbonato-bridged copper(II) complex as well as a dinuclear copper(I) complex with BP ligands were structurally characterized. The reaction of a copper(I)–BP complex was investigated by low-temperature stopped-flow techniques, which showed that the very fast formation of a bis(µ-oxido)copper intermediate leads to an intramolecular ligand hydroxylation. However, substrates such as benzyl alcohol could also be oxidized with this complex. In contrast, no intermediates could be observed spectroscopically for complexes with the BQ ligand or derivatives of this ligand. Instead, complex reaction behavior was observed when copper(II) chloride was treated with BQ in air or under inert conditions. Several crystal structures helped to establish mechanisms for these reactions. A coordination polymer was obtained as an interesting reaction product. Copper complexes with bis(piperidinyl)methane (BP) ligands can form a bis(µ-oxido) intermediate, which is capable of not only intramolecular ligand hydroxylation but also the oxidation of substrates, (for example, benzyl alcohol to benzaldehyde). In contrast, copper complexes with sterically more demanding bis(quinolinyl)methane (BQ) ligands are not useful for substrate oxidation reactions.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/ejic.201700755

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