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The Use of Calcium Carbide as Acetylene Source in a Three-Component Coupling with ω-Chlorinated Ketones and Primary
Wim E Van Beek1, Karthik Gadde1, Kourosch Abbaspour Tehrani1
1Research Group Organic Synthesis, Department of Chemistry, University of Antwerp, Groenenborgerlaan 171, 2020, Antwerp, Belgium.
Abstract:
Calcium carbide was used in a CuI -catalysed three-component coupling with ω-chlorinated ketones and primary amines to generate terminal 2-alkynyl-N-heterocycles. The formation of an imine and the subsequent intramolecular substitution results in an active electrophilic iminium species, which can be alkynylated by in situ formed copper acetylide. A number of aliphatic primary (functionalised) amines and aliphatic or aromatic alkynes together with different alkyl- or aryl-substituted γ- or δ-chloroketones could be used. Simple acid-base workup instead of column chromatography can be applied to obtain the resulting 2-alkynylpyrrolidines and 2-alkynylpiperidines.
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