Synthesis of 9-alkylidene-9H-fluorenes by a novel palladium-catalyzed rearrangement
In the presence of a palladium catalyst and NaOAc, aryl iodides react with 1-aryl-1-alkynes to afford 9-alkylidene-9H-fluorenes in good yields. This process appears to involve (1) oxidative addition of the aryl iodide to Pd(0), (2) alkyne insertion, (3) rearrangement of the resulting vinylic palladium intermediate to an arylpalladium species, and (4) aryl-aryl coupling with simultaneous regeneration of the Pd(0) catalyst.
Tian
Q
Department of Chemistry, Iowa State University, Ames, Iowa 50011, USA.
Larock
RC