Palladacycles bearing pendant benzamidinate ligands as catalysts for the Suzuki and Heck coupling reactions

Three pendant benzamidines [Ph–C(double bond; length as m-dashNC6H5)–{NH(CH2)2NMe2}] (), [Ph–C(double bond; length as m-dashNC6H5)–{NH(CH2Py)}] () and [Ph–C(double bond; length as m-dashNC6H5)-{NH(o-C6H4)(oxazoline)}] () are described. Reactions of , or with one molar equivalent of Pd(OAc)2 in THF give the palladacyclic complexes [Ph–C{–NH(η1-C6H4)}{double bond; length as m-dashN(CH2)2NMe2}]Pd(OAc) (), [Ph–C{–NH(η1-C6H4)}{double bond; length as m-dashN (CH2Py)}]Pd(OAc) () and [Ph–C{–NH(η1-C6H4)}{double bond; length as m-dashN(o-C6H4)(oxazoline)}]Pd(OAc) (), respectively. Treatment of , or with excess of LiCl in chloroform affords [Ph–C{–NH(η1-C6H4)}{double bond; length as m-dashN(CH2)2NMe2}]PdCl (), [Ph–C{–NH(η1-C6H4)}{double bond; length as m-dashN(CH2Py)}]PdCl () and [Ph–C{–NH(η1-C6H4)}{double bond; length as m-dashN(o-C6H4)(oxazoline)}]PdCl (). The crystal and molecular structures are reported for compounds , , , and . The application of these palladacyclic complexes to the Suzuki and Heck coupling reactions was examined.