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research article
Ketenimines from Isocyanides and Allyl Carbonates: Palladium-Catalyzed Synthesis of β,γ-Unsaturated Amides and Tetrazoles
The reaction of allyl ethyl carbonates with isocyanides in the presence of a catalytic amount of Pd(OAc)2 provided ketenimines through b-hydride elimination of the allyl imidoylpalladium intermediates. The insertion of the isocyanide into the p-allyl Pd complex proceeded via an unusual h1-allyl Pd species. The resulting ketenimines were hydrolyzed to b,g-unsaturated carboxamides during purification by flash column chromatography on silica gel or converted in situ into 1,5-disubstituted tetrazoles by [3+2] cycloaddition with hydrazoic acid or trimethylsilyl azide.
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Type
research article
Web of Science ID
WOS:000389224000036
Publication date
2016
Publisher
Published in
Volume
55
Issue
49
Start page
15377
End page
15381
Peer reviewed
REVIEWED
EPFL units
Available on Infoscience
November 30, 2016