화학공학소재연구정보센터
Chemistry Letters, Vol.40, No.9, 967-969, 2011
Chemoselective Transfer of Allyl or Phenyl Group from Allyl(phenyl)germanes in Pd-catalyzed Reactions with Aryl Halides
Treatment of chloro(phenyl)germanes with allylmagnesium bromide yielded allyl(phenyl)germanes. Coupling of the allyl(phenyl)germanes with aryl halides in 1,4-dioxane in the presence of aqueous NaOH and Pd catalyst resulted in Fleck-type transfer of the allyl group providing the corresponding allylated aryls. On the other hand, reaction of allyl(phenyl)germanes with SbF5 intercalated in graphite in toluene and subsequent treatment of the resulting germanyl fluorides with TBAF generates reactive hypervalent fluorogermanates that undergo Stille-like Pd-catalyzed cross-coupling with aryl halides in wet toluene to provide biaryls.