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Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
Published on: July 30, 2017
Palladium-catalyzed oxidative activation of arylcyclopropanes
1Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, Canada M5S 3H6.
Abstract:
Palladium chloride-catalyzed intramolecular activation of electroneutral cyclopropane derivatives results in cleavage of the cyclopropane ring followed by formation of heterocyclic derivatives. Phenols, carboxylic acids, and amide groups were considered as substituents ortho to the cyclopropane ring in this catalytic activation chemistry. The regioselectivity observed in the case of amide-containing substrates was different from that of carboxylic acid-containing substrates, ruling out simple cyclopropane isomerization followed by a Wacker oxidation as the mechanistic pathway. [reaction: see text]
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