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Full Paper
Fe-Catalyzed Multicomponent Reactions: The Regioselective Alkoxy Allylation of Activated Olefins and its Application in Sequential Fe Catalysis
Article first published online: 16 JAN 2012
DOI: 10.1002/chem.201103009
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Dieskau, A. P., Holzwarth, M. S. and Plietker, B. (2012), Fe-Catalyzed Multicomponent Reactions: The Regioselective Alkoxy Allylation of Activated Olefins and its Application in Sequential Fe Catalysis. Chem. Eur. J., 18: 2423–2429. doi: 10.1002/chem.201103009
Publication History
- Issue published online: 10 FEB 2012
- Article first published online: 16 JAN 2012
- Manuscript Received: 26 SEP 2011
Funded by
- Studienstiftung des Deutschen Volkes
- Deutsche Forschungsgemeinschaft
Keywords:
- allylation;
- catalysis;
- iron;
- Michael addition;
- multicomponent reactions
Abstract
We present herein a versatile and broadly applicable Fe-catalyzed regioselective alkoxy allylation of activated double bonds. Substituted allylic carbonates are converted into the corresponding σ-enyl Fe complexes by reaction with Bu4N[Fe(CO)3(NO)] (TBAFe) at 30 °C. The liberated alkoxide adds to an activated double bond with the generation of a C-nucleophile, which is trapped by the σ-enyl Fe complex in a regioselective manner. Alternatively, the alkoxide acts as a base in deprotonating an external pronucleophile, which undergoes Michael addition. The method is characterized by a broad functional group tolerance, mild reaction conditions, low catalyst loadings, and high regioselectivities in favor of the ipso-substitution product.