Palladium-catalyzed direct C-h arylation of N-iminopyridinium ylides: application to the synthesis of (+/-)-anabasine.
Palladium-catalyzed direct C-H arylation of N-iminopyridinium ylides provides a powerful and versatile method for the synthesis of functionalized piperidines in good yields. Chemoselective functionalization of the pyridinium ring in the presence of a pyridine substituent is possible as exemplified by the expedient synthesis of anabasine in 61% overall yield over three steps.
Larivée
Alexandre
A
Department of Chemistry, Université de Montréal, P. O. Box 6128, Station Downtown, Montréal, Quebec, Canada H3C 3J7.
Mousseau
James J
JJ
Charette
André B
AB
D000691:Anabasine / Q000138:chemical synthesis*; D002384:Catalysis; D006841:Hydrocarbons, Aromatic; D007306:Insecticides / Q000138:chemical synthesis; D010165:Palladium; D010880:Piperidines / Q000138:chemical synthesis; D011725:Pyridines
D006841:Hydrocarbons, Aromatic; D007306:Insecticides; D010880:Piperidines; D011725:Pyridines; D010165:Palladium; D000691:Anabasine