5,5″-disubstituted 2,2′:6′,2″-terpyridines through and for metal-mediated cross-coupling chemistry

Article abstract of DOI:10.1002/(SICI)1521-3765(19990301)5:3<854::AID-CHEM854>3.0.CO;2-8

The 0.3-5 g scale syntheses of the 2,2′:6′,2″-terpyridines 3, 6, 9, and 10 are described. The pyridine units are connected to one another by Pd-catalyzed cross-coupling reactions. This method allows the easy introduction of halogen, stannyl, and boronic ester functionalities at positions C-5 and C-5″; this results in a novel functionality pattern for terpyridines that considerably widens the applicability of this class of tridentate ligands for supra- and macromolecular applications. The feasibility of growth reactions with these novel terpyridines was demonstrated by the synthesis of compounds 12a-c.