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Copper-Catalyzed Dehydration of Primary Amides to Nitriles

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Abstract

In the present study we introduce a copper-catalyzed protocol for the dehydration of primary amides to their corresponding nitriles applying N-methyl-N-(trimethylsilyl)trifluoroacetamide (MSTFA) as silylation reagent. For that purpose investigations of various reaction parameters (copper source, solvent, temperature, MSTFA and copper loading) have been carried out to find suitable reaction conditions. Simple copper(I) chloride (2.5 mol%) and MSTFA (2.0 equiv) in toluene allow for the straightforward synthesis of a variety of nitriles (15 examples).

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Acknowledgment

Financial support from the Cluster of Excellence “Unifying Concepts in Catalysis” (funded by the Deutsche Forschungsgemeinschaft and administered by the Technische Universität Berlin) is gratefully acknowledged.

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Authors and Affiliations

  1. Department of Chemistry, Cluster of Excellence Unifying Concepts in Catalysis, Technische Universität Berlin, Straße des 17. Juni 135/C2, 10623, Berlin, Germany

    Stephan Enthaler & Maik Weidauer

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  1. Stephan Enthaler
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  2. Maik Weidauer
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Correspondence to Stephan Enthaler.

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Enthaler, S., Weidauer, M. Copper-Catalyzed Dehydration of Primary Amides to Nitriles. Catal Lett 141, 1079–1085 (2011). https://doi.org/10.1007/s10562-011-0660-9

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  • DOI: https://doi.org/10.1007/s10562-011-0660-9

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