Palladium-catalyzed oxidative activation of arylcyclopropanes.
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]
He
Zhi
Z
Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, Canada M5S 3H6.
Yudin
Andrei K
AK
D000577:Amides / Q000737:chemistry; D002384:Catalysis; D003521:Cyclopropanes / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000138:chemical synthesis; D007769:Lactams / Q000138:chemical synthesis; D009682:Magnetic Resonance Spectroscopy; D010084:Oxidation-Reduction; D010165:Palladium / Q000737:chemistry*
D000577:Amides; D003521:Cyclopropanes; D006571:Heterocyclic Compounds; D007769:Lactams; D010165:Palladium