Synthesis of 3,3-Disubstituted-2,2-bipyridines from 1,10-Phenanthroline-5,6-quinone

A route to 3,3ʹ-disubstituted-2,2ʹ-bipyridines from 1,10-phenanthroline-5,6-quinone is described. The methodology involves the 1,2-addition of an organometallic reagent to the quinone, followed by lead tetraacetate cleavage of the diol. This, in turn, is followed by L?che or Wolf–Kishner reduction affording diols or alkanes respectively.