This research was funded by the National Research School Combination Catalysis (project no. 2004–2008-UVA-Elsevier-02/03). G.M. was the recipient of a Socrates/Erasmus fellowship from the University of Parma. We thank Dr. G. Rothenberg for helpful discussions and a critical reading of the manuscript.
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Communication
Transfer Semihydrogenation of Alkynes Catalyzed by a Zero-Valent Palladium N-Heterocyclic Carbene Complex†
Article first published online: 13 MAR 2008
DOI: 10.1002/anie.200705638
Copyright © 2008 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Hauwert, P., Maestri, G., Sprengers, J. W., Catellani, M. and Elsevier, C. (2008), Transfer Semihydrogenation of Alkynes Catalyzed by a Zero-Valent Palladium N-Heterocyclic Carbene Complex. Angewandte Chemie International Edition, 47: 3223–3226. doi: 10.1002/anie.200705638
- †
Publication History
- Issue published online: 8 APR 2008
- Article first published online: 13 MAR 2008
- Manuscript Received: 10 DEC 2007
Funded by
- National Research School Combination Catalysis. Grant Number: 2004–2008-UVA-Elsevier-02/03
Keywords:
- alkynes;
- carbene ligands;
- hydrogen transfer;
- hydrogenation;
- palladium
Graphical Abstract
Beyond Lindlar and without hydrogen: Transfer hydrogenation of internal alkynes catalyzed by a palladium(0) catalyst containing an N-heterocyclic carbene ligand gives Z alkenes without over-reduction to alkanes (see scheme). Contrary to most transfer hydrogenations, ketones are not reduced. As such, this is the first catalyst that shows excellent stereo- and chemoselectivity for the semihydrogenation of alkynes without the need for hydrogen gas.