Issue 12, 2015

Cyclometallated gold(iii) aryl-pyridine complexes as efficient catalysts for three-component synthesis of substituted oxazoles

Abstract

Cyclometallated aryl-pyridine gold(III) complexes are shown to be efficient catalysts for the multicomponent reaction between N-benzyl imines, alkynes, and acyl chlorides to form trisubstituted oxazoles. The reaction typically proceeds in good yields (up to over 80%) and short reaction times (∼15 minutes). The high stability of the investigated cyclometallated catalysts enables a retained efficiency for this reaction in terms of rate and yield using as little as 0.5 mol% catalyst, a reduction by an order of magnitude compared to previously used Au(III)–salen complexes. An attractive feature of the present catalytic system is that active catalysts can be formed from simple pre-catalysts under the reaction conditions. Both cyclometallated and non-cyclometallated complexes were characterized in the solid state by single crystal X-ray diffraction.

Graphical abstract: Cyclometallated gold(iii) aryl-pyridine complexes as efficient catalysts for three-component synthesis of substituted oxazoles

Supplementary files

Article information

Article type
Paper
Submitted
11 Dec 2014
Accepted
09 Feb 2015
First published
09 Feb 2015
This article is Open Access
Creative Commons BY-NC license

Dalton Trans., 2015,44, 5347-5353

Author version available

Cyclometallated gold(III) aryl-pyridine complexes as efficient catalysts for three-component synthesis of substituted oxazoles

H. von Wachenfeldt, A. V. Polukeev, N. Loganathan, F. Paulsen, P. Röse, M. Garreau, O. F. Wendt and D. Strand, Dalton Trans., 2015, 44, 5347 DOI: 10.1039/C4DT03806A

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