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Allyl versus aryl C-H activation mediated by palladium acetate

Authors
Journal
Journal of Organometallic Chemistry
0022-328X
Publisher
Elsevier
Publication Date
Volume
548
Issue
2
Identifiers
DOI: 10.1016/s0022-328x(97)00450-6
Keywords
  • Amine
  • Allyl
  • Aryl
  • Cyclometallation
  • Catalysis
  • Palladium

Abstract

Abstract In the presence of a catalytic amount of palladium acetate and a 2:1 stoichiometry of 1,4-benzoquinone, N,N-dimethyl-2-propenylbenzenemethylamine afforded N,N-dimethyl-2-benzazepinium in up to 85% yield. Under similar conditions related N,N-dimethyl-2-propenylbenzenamine and N,N-dimethyl-2-butenylbenzene-methylamine afforded the quinolinium and the isoquinolinium derivatives with 85 and 21% yields, respectively. Running these reactions in the presence of stoichiometric amounts of palladium acetate led to the formation of cyclopalladated compounds formed by the orthopalladation of the aryl ring. Thus, under these latter conditions the aromatic C-H activation is in competition with the allylic one.

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