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Synlett 1992; 1992(5): 435-438
DOI: 10.1055/s-1992-21372
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Reaction of Dicobalthexacarbonyl Propargyl Cations with Aldehydic N,N-Dibenzylenamines

Klaus-Dieter Roth*
  • *Institut für Organische Chemie der Universität Erlangen, Henkestr.42, D-8520 Erlangen, Germany
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Publication Date:
08 March 2002 (online)

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The reaction of cobalt-complexed propargylic cations 1 with aldehydic N,N-dibenzylenamines 2 is described, leading to iminium ions 3. These intermediates can be treated in a one-pot reaction with nucleophiles (Grignard reagents, Me3SiCN) to yield cobalt-complexed N,N-dibenzyl-4-alkynylamines 4, thus utilizing for the first time enamines for a Nicholas reaction. Compounds 4 can be efficiently demetalated to the corresponding N,N-dibenzyl-4-alkynylamines 5, which could possibly serve as building blocks for the synthesis of 5- and 6-membered N-heterocycles.

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