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Communication | Regular issue | Vol 65, No. 2, 2005, pp.273-277
Published online, 24th December, 2004
DOI: 10.3987/COM-04-10280
Palladium(0)-catalyzed Amino-Heck Reaction of γ,δ-Unsaturated Ketone N,N,N-Trimethylhydrazonium Salts

Mitsuru Kitamura, Hideyuki Yanagisawa, Motoki Yamane, and Koichi Narasaka*

*Department of Chemistry, Graduate School of Science, University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan


Oxidative addition of N,N,N-trialkylhydrazonium salts takes place to a palladium(0) complex, resulting the formation of alkylideneaminopalladium(II) species. This N–N bond scission process is applied to the transformation of γ,δ-unsaturated ketone hydrazonium salts to pyrroles by amino-Heck reaction.