Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 18, Issue 38, Pages 12112-12121Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201201448
Keywords
carbenes; gold catalysts; hydroamination; imidazoles; N-heterocyclic carbenes
Categories
Funding
- Natural Sciences and Engineering Research Council of Canada (NSERC)
- NSERC Research and Tools Instrumentation Grant
- Canadian Foundation for Innovation
- Ontario Research Fund for Infrastructure Funding
- York University
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Gold(I) complexes of 1-[1-(2,6-dimethylphenylimino)alkyl]-3-(mesityl)imidazol-2-ylidene (C boolean AND ImineR), 1,3-dimesitylimidazol-2-ylidene (IMes) and of the corresponding thione derivatives (S boolean AND Imine(R) and IMesS) were prepared and structurally characterised. The solid-state structure of the C boolean AND Imine(R) and S boolean AND Imine(R) gold(I) complexes showed monodentate coordination of the ligand and a dangling imine group that could bind reversibly to the metal centre to stabilise otherwise unstable catalytic intermediates. Interestingly, reaction of C boolean AND Imine(tBu) with [AuCl(SMe2)] led to the formation of [(C boolean AND Imine(tBu))AuCl], which rearranges upon crystallisation into the unusual complex cation [(C boolean AND Imine(tBu))(2)Au](+), with AuCl2- as the counterion. The activity of the gold complexes in the hydroamination of phenylacetylene with substituted anilines was tested and compared to control catalyst systems. The best catalytic performance was obtained with [(C boolean AND Imine(tBu))AuCl], with the exclusive formation of the Markovnikov addition product in excellent yield (>95?%) regardless of the substituents on aniline.
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