Synthesis, structure, and metal complexation behavior of a new type of functionalized chiral phenanthroline derivative.

SmI(2) serves as an effective promoter for the coupling of 1,10-phenanthroline with an epoxide to generate a new class of chiral, functionalized ligands that readily form complexes with metals. Structural studies of the resulting phenanthroline derivative and two of its metal complexes are reported.

Samarium-promoted coupling of pyridine-based heteroaryl analogues of benzylic acetates with carbonyl compounds.

2-Substituted pyridine, quinoline, isoquinoline, bipyridine, and 1,10-phenanthroline analogues of benzylic acetates undergo SmI(2)-promoted coupling with aldehydes and ketones to afford (2-hydroxyalkyl)heteroaromatics. [reaction: see text]

Samarium-promoted coupling of 1,10-phenanthroline with carbonyl compounds for synthesis of new ligands.

1,10-Phenanthroline reacts with aldehydes and ketones in the presence of samarium diiodide to produce 2-(1-hydroxyalkyl)-1,10-phenanthrolines. The hydroxyalkyl substituent can be functionalized in numerous ways or removed to permit further ligand variation. The carbonyl coupling reaction can also be repeated to provide 2,9-disubstituted phenanthrolines.