Synthesis of 9-fluorenylidenes and 9,10-phenanthrenes through palladium-catalyzed aryne annulation by o-halostyrenes and o-halo allylic benzenes.
A number of functionally substituted 9-fluorenylidenes and 9,10-phenanthrenes have been synthesized from substituted o-halostyrenes and o-halo allylic benzenes respectively in good yields by the palladium-catalyzed annulation of arynes. The methodology tolerates a variety of functional groups, including cyano, ester, aldehyde, and ketone groups, occurs under relatively mild reaction conditions, and involves the generation of two new carbon-carbon bonds, thus providing these important carbocyclic ring systems in a single synthetic step.
Worlikar
Shilpa A
SA
Department of Chemistry, Iowa State University, Ames, Iowa 50011, USA.
Larock
Richard C
RC
D000498:Allyl Compounds; D001554:Benzene; D002384:Catalysis; D005449:Fluorenes / Q000138:chemical synthesis*; D008722:Methods; D010165:Palladium; D010616:Phenanthrenes / Q000138:chemical synthesis*; D013343:Styrenes
D000498:Allyl Compounds; D005449:Fluorenes; D010616:Phenanthrenes; D013343:Styrenes; D010165:Palladium; D001554:Benzene