Oxidation of 2,9‐Diphenyl‐1,10‐phenanthroline to Generate the 5,6‐Dione and Its Subsequent Alkylation Product

• DOI: 10.1002/jhet.2105
• Publication Date: 2014-01-30T22:42:09Z
• Authors: Ammon P. Lehnig; Megan S. Lazorski; Michael Mingroni; Kimberly A. O. Pa...; C. Michael Elliott
• Keywords: Phenanthroline

One group of ligands used in transition metal complexes is synthesized by derivatizing 1,10‐phenanthroline. These are interest for study the field photovoltaic devices and solar fuels. Previous strategies obtaining 5,6‐diones substituted 1,10‐phenanthrolines do not work 2,9‐diphenyl‐1,10‐phenanthroline due to undesired products resulting from oxidation phenyl substituents. However, 2,9‐diphenyl‐1,10‐phenanthroline‐5,6‐dione can be obtained reasonable yield with BrO 3 − weak aqueous acid. The dione converted directly 5,6‐dialkoxy product upon two electron reduction aprotic solvent followed treatment appropriate alkylating agents.