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Updated: May 10, 2026

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Pd-catalyzed bis-cyclization/dimerization reactions of ω-aminovinyl halides
Avinash Khanna1, Ilandari Dewage Udara Anulal Premachandra, Paul D Sung
1Departmentof Chemistry, University of California at Irvine, Irvine, California 92697-2025, USA.
Abstract:
Palladium is shown to catalyze the dimerization and cyclization of vinyl halides to generate pyrrolidine and piperidine dimers connected by a trans-ethylene bridge. The reaction tolerates a variety of N-alkyl substituents, including adamantyl. This remarkable dimerization reaction generates the skeleton of the alkaloid hyalbidone in a single step. A crossover experiment with a vinyl halide and a vinyl bromide is consistent with a Michael-type addition to a vinylpalladium cation to generate a Pd(0) alkylidene intermediate.
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