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Issue 1, 2017
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Phosphinines versus mesoionic carbenes: a comparison of structurally related ligands in Au(i)-catalysis

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Abstract

Gold(I) complexes based on a 2,4,6-triarylphosphinine and a mesoionic carbene derivative have been prepared and characterized crystallographically. Although structurally related, both heterocycles differ significantly in their donor/acceptor properties. These opposed electronic characteristics have been exploited in Au(I)-catalyzed cycloisomerization reactions. For the conversion of the standard substrate dimethyl 2-(3-methylbut-2-enyl)-2-(prop-2-ynyl)malonate the results obtained for both Au-catalysts were found to be very similar and comparable to the ones reported in the literature for other carbene- or phosphorus(III)-based Au(I)-complexes. In contrast, a clear difference between the catalytic systems was found for the cycloisomerization of the more challenging substrate N-2-propyn-1-ylbenzamide. A combination of the phosphinine-based complex and [AgSbF6] or [Cu(OTf)2] leads to a catalytic species, which is more active than the mesoionic carbene-based coordination compound. We attribute these differences to the stronger π-accepting ability of phosphinines in comparison to mesoionic carbenes. The here presented results show for the first time that phosphinines can be used efficiently as π-accepting ligands in Au(I)-catalyzed cycloisomerization reactions.

Graphical abstract: Phosphinines versus mesoionic carbenes: a comparison of structurally related ligands in Au(i)-catalysis

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Supplementary files

Article information


Submitted
28 Sep 2016
Accepted
20 Nov 2016
First published
29 Nov 2016

Dalton Trans., 2017,46, 86-95
Article type
Paper

Phosphinines versus mesoionic carbenes: a comparison of structurally related ligands in Au(I)-catalysis

M. Rigo, L. Hettmanczyk, F. J. L. Heutz, S. Hohloch, M. Lutz, B. Sarkar and C. Müller, Dalton Trans., 2017, 46, 86
DOI: 10.1039/C6DT03766F

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