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Short Communication
Direct Hydrosilylation of Tertiary Amides to Amines by an In Situ Formed Iron/N-Heterocyclic Carbene Catalyst
Article first published online: 1 MAR 2013
DOI: 10.1002/ejoc.201300010
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Volkov, A., Buitrago, E. and Adolfsson, H. (2013), Direct Hydrosilylation of Tertiary Amides to Amines by an In Situ Formed Iron/N-Heterocyclic Carbene Catalyst. Eur. J. Org. Chem., 2013: 2066–2070. doi: 10.1002/ejoc.201300010
Publication History
- Issue published online: 3 APR 2013
- Article first published online: 1 MAR 2013
- Manuscript Received: 4 JAN 2013
Keywords:
- Hydrosilylation;
- Iron;
- Carbenes;
- Amides;
- Amines
Abstract
Tertiary amides were efficiently reduced to their corresponding tertiary amines in high isolated yields by using the commercially available and inexpensive polymeric silane polymethylhydrosiloxane (PMHS) as the reducing agent. The reaction is efficiently catalyzed by an in situ generated iron/N-heterocyclic carbene complex (1 mol-%) obtained from iron(II) acetate and 1-(2-hydroxy-2-phenylethyl)-3-methylimidazolium triflate ([PhHEMIM][OTF]). A catalytic amount of lithium chloride (1 mol-%) present in the reaction mixture significantly reduced the reaction time and increased the chemoselectivity of the reduction process.