Phenylsilatrane analogues containing reactive amino, bromo, boronic ester, and alkynyl functional groups for coupling reactions have been prepared. Pinacol boronic ester and ethynyl analogues were synthesized from 4-bromophenylsilatrane by palladium catalyzed reactions. The silatrane functional group was shown to be stable during the palladium catalysis procedures and silica-gel purification, making the molecules amenable to further synthetic manipulation. The described phenylsilatranes are useful building blocks for forming more complex organosilatrane species.