O'Neill D J, Helquist P
Department of Chemistry, University of Notre Dame, Indiana 46556, USA.
Org Lett. 1999 Nov 18;1(10):1659-62. doi: 10.1021/ol990284w.
[formula: see text] 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.
[化学式：见正文] 1,10-菲咯啉在二碘化钐促进下与酮发生偶联反应，生成2-(1-羟烷基)-1,10-菲咯啉。这些衍生物的O-甲基化反应可得到相应的2-(1-甲氧基烷基)菲咯啉。然后用二碘化钐进行脱甲氧基反应可得到2-烷基菲咯啉。该过程可重复进行以获得2,9-二取代菲咯啉。由此可得到多种新型的、取代的菲咯啉。这些化合物作为配体在金属促进的反应（包括不对称催化）中具有众多潜在应用。
