4.8 Article

Ketenimines from Isocyanides and Allyl Carbonates: Palladium-Catalyzed Synthesis of β,γ-Unsaturated Amides and Tetrazoles

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 49, Pages 15377-15381

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201609034

Keywords

isocyanides; ketenimines; palladium; tetrazoles; beta,gamma-unsaturated amides

Funding

  1. EPFL (Switzerland)
  2. Swiss National Science Foundation (SNSF)

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The reaction of allyl ethyl carbonates with isocyanides in the presence of a catalytic amount of Pd(OAc)(2) provided ketenimines through -hydride elimination of the allyl imidoylpalladium intermediates. The insertion of the isocyanide into the -allyl Pd complex proceeded via an unusual (1)-allyl Pd species. The resulting ketenimines were hydrolyzed to ,-unsaturated carboxamides during purification by flash column chromatography on silica gel or converted insitu into 1,5-disubstituted tetrazoles by [3+2] cycloaddition with hydrazoic acid or trimethylsilyl azide.

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