title: Palladium-catalyzed direct C-h arylation of N-iminopyridinium ylides: application to the synthesis of (+/-)-anabasine.
abstract: 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.
authors: Department of Chemistry, Université de Montréal, P. O. Box 6128, Station Downtown, Montréal, Quebec, Canada H3C 3J7.
authors: Alexandre
authors: A
authors: Larivée
authors: James J
authors: JJ
authors: Mousseau
authors: André B
authors: AB
authors: Charette
mesh_terms: D000691:Anabasine / Q000138:chemical synthesis*; D002384:Catalysis; D006841:Hydrocarbons, Aromatic; D007306:Insecticides / Q000138:chemical synthesis; D010165:Palladium; D010880:Piperidines / Q000138:chemical synthesis; D011725:Pyridines
chemical_list: D006841:Hydrocarbons, Aromatic; D007306:Insecticides; D010880:Piperidines; D011725:Pyridines; D010165:Palladium; D000691:Anabasine