Seleniranium ion-triggered reactions: new aspects of Friedel-Crafts and N-detosylative cyclizations.
Seleniranium ions at low temperatures (-90 to -78 degrees C) will initiate effective Friedel-Crafts cyclization if a suitably placed arene is allowed to react even when the arene is unactivated. These intermediates generated from N-aryl-N-tosylamides undergo a novel, surprisingly efficient, detosylative cyclization to form 5- or 6-membered nitrogen heterocycles. A debenzylation route is preferred if both benzyl and tosyl groups are present in the substrate.
Lim
Hwan Jung
HJ
Department of Chemistry, The Ohio State University, 100 West 18th Avenue, Columbus, Ohio 43210, USA.
RajanBabu
T V
TV
D001393:Azoles / Q000737:chemistry; D001555:Benzene Derivatives / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D003080:Cold Temperature; D003500:Cyclization; D015394:Molecular Structure; D016566:Organoselenium Compounds / Q000138:chemical synthesis / Q000737:chemistry*
D001393:Azoles; D001555:Benzene Derivatives; D016566:Organoselenium Compounds