A utility for organoleads: selective alkyl and aryl group transfer to tin

Me₄Pb and Ph₄Pb readily transfer methyl or phenyl groups to an equivalent molar ratio of tin(IV) chlorides in the order SnCl₄ > MeSnCl₃ > Me₂SnCl₂ > Me₃SnCl, often in a selective manner. Me₃PbCl and Ph₃PbCl specifically transfer a single methyl/phenyl group under the same reaction conditions to produce recovered yields in >75%. Specific transfer of 2 methyl groups from PbMe₄ can be achieved at elevated temperatures and/or a 2 : 1 molar ratio Pb : Sn.