American Chemical Society
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Facile Synthesis of Substituted Phenanthroline Ligands by Samarium-Promoted Coupling of Phenanthroline with Ketones

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journal contribution
posted on 1999-10-10, 00:00 authored by David J. O'Neil, Paul Helquist
1,10-Phenanthroline undergoes coupling with ketones promoted by samarium diiodide to produce 2-(1-hydroxyalkyl)-1,10-phenanthrolines. O-Methylation of these derivatives provides the corresponding 2-(1-methoxyalkyl)phenanthrolines. Demethoxylation with samarium diiodide then affords 2-alkylphenanthrolines. This process may be repeated to obtain 2,9-disubstituted phenanthrolines. A variety of new, substituted phenanthrolines are thus obtained. These compounds have numerous potential applications as ligands in metal-promoted reactions, including asymmetric catalysis.