A General Method of Synthesis of Regiospecifically N-Oxidized or N-Quaternized Polyazines by Palladium-Catalyzed Cross-Coupling of N-Oxidized or N-Quaternized Hetaryl Stannanes

N-Oxides of tributylstannylated pyridine, quinoline, and isoquinoline and tributylstannylated N-methiodides of pyridine and quinoline were readily prepared, many for the first time. In the presence of a palladium catalyst these materials were cross-coupled to various chloro, bromo, and iodo hetaryl halides to give polyazines having the N-functional group placed unequivocally in eleven different polycyclic ring systems. The use of tosylate as a counterion with quaternized salts minimized decomposition of the stannane.