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Issue 19, 2015
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The fluxional amine gold(iii) complex as an excellent catalyst and precursor of biologically active acyclic carbenes

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Abstract

A new amine gold(III) complex [Au(C6F5)2(DPA)]ClO4 with the di-(2-picolyl)amine (DPA) ligand has been synthesised. In the solid state the complex has a chiral amine nitrogen because the ligand coordinates to the gold centre through one nitrogen atom from a pyridine and through the NH moiety, whereas in solution it shows a fluxional behaviour with a rapid exchange between the pyridine sites. This complex can be used as an excellent synton to prepare new gold(III) carbene complexes by the reaction with isocyanide CNR. The resulting gold(III) derivatives have unprecedented bidentate C^N acyclic carbene ligands. All the complexes have been spectroscopically and structurally characterized. Taking advantage of the fluxional behaviour of the amine complex, its catalytic properties have been tested in several reactions with the formation of C–C and C–N bonds. The complex showed excellent activity with total conversion, without the presence of a co-catalyst, and with a catalyst loading as low as 0.1%. These complexes also present biological properties, and cytotoxicity studies have been performed in vitro against three tumour human cell lines, Jurkat (T-cell leukaemia), MiaPaca2 (pancreatic carcinoma) and A549 (lung carcinoma). Some of them showed excellent cytotoxic activity compared with the reference cisplatin.

Graphical abstract: The fluxional amine gold(iii) complex as an excellent catalyst and precursor of biologically active acyclic carbenes

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Publication details

The article was received on 16 Feb 2015, accepted on 09 Apr 2015 and first published on 09 Apr 2015


Article type: Paper
DOI: 10.1039/C5DT00703H
Dalton Trans., 2015,44, 9052-9062

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    The fluxional amine gold(III) complex as an excellent catalyst and precursor of biologically active acyclic carbenes

    S. Montanel-Pérez, R. P. Herrera, A. Laguna, M. D. Villacampa and M. C. Gimeno, Dalton Trans., 2015, 44, 9052
    DOI: 10.1039/C5DT00703H

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