The exact nature of the gold–carbon bond formed during homogeneous gold catalysis has recently attracted a lot of interest and is somewhat controversial. Now a study of the bonding and trends in reactivity of various gold complexes offers new insights into whether such structures can be defined as gold-stabilized cations or gold carbenes.
References
Olah, G. A. J. Org. Chem. 70, 2413–2429 (2005).
Lavallo, V., Dyker, C. A., Donnadieu, B. & Bertrand, G. Angew. Chem. Int. Ed. 48, 1540–1542 (2009).
Benitez, D. et al. Nature Chem. 1, 482–486 10.1038/nchem.331(2009).
Fürstner, A. & Morency, L. Angew. Chem. Int. Ed. 47, 5030–5033 (2008).
Seidel, G., Mynott, R. & Fürstner, A. Angew. Chem. Int. Ed. 48, 2510–2513 (2009).
Jiménez-Núñez, E. & Echavarren, A. M. Chem. Rev. 108, 3326–3350 (2008).
Gorin, D. J., Sherry, B. D. & Toste, F. D. Chem. Rev. 108, 3351–3378 (2008).
Steinborn, D. et al. Z. Anorg. Allg. Chem. 624, 1303–1307 (1998).
Johansson, M. J., Gorin, D. J., Staben, S. T. & Toste, F. D. J. Am. Chem. Soc. 127, 18002–18003 (2005).
López, S., Herrero-Gómez, E., Pérez-Galán, P., Nieto-Oberhuber, C. & Echavarren, A. M. Angew. Chem. Int. Ed. 45, 6029–6032 (2006).
Jiménez-Núñez, E., Claverie, C. K., Bour, C., Cárdenas, D. J. & Echavarren, A. M. Angew. Chem. Int. Ed. 47, 7892–7895 (2008).
Fañanás-Mastral, M. & Aznar, F. Organometallics 28, 666–668 (2009).
Snyder, J. P. et al. J. Am. Chem. Soc. 123, 11318–11319 (2001).
Straub, B. F. Angew. Chem. Int. Ed. 44, 5974–5978 (2005).
Tantillo, D. J. & Hoffmann, R. J. Am. Chem. Soc. 123, 9855–9859 (2001).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Echavarren, A. Carbene or cation?. Nature Chem 1, 431–433 (2009). https://doi.org/10.1038/nchem.344
Issue Date:
DOI: https://doi.org/10.1038/nchem.344
- Springer Nature Limited
This article is cited by
-
Gold(I)-catalyzed intramolecular cyclization/intermolecular cycloaddition cascade as a fast track to polycarbocycles and mechanistic insights
Nature Communications (2021)
-
Synthesis and structures of gold and copper carbene intermediates in catalytic amination of alkynes
Nature Communications (2017)
-
A ligand-directed divergent catalytic approach to establish structural and functional scaffold diversity
Nature Communications (2017)
-
Metal-Diazo Radicals of α-Carbonyl Diazomethanes
Scientific Reports (2016)