Palladium-Catalyzed Cross-Coupling Reactions of Allyl, Phenyl, Alkenyl, and Alkynyl Germatranes with Aryl Iodides

The potential of using organogermatranes in palladium-catalyzed cross-coupling with aryl
iodides has been investigated. We have found that organogermatranes are less reactive in
this analogue of Stille coupling than trialkylorganostannanes; nevertheless activation by
fluoride promotes the reaction. The hypervalent germanium species produced from the
germatranes provide a more efficient and more easily handled reagent than trialkoxygermanium analogues.