Synthesis of 5,5'-Diarylimino Quinoidal 2,2'-Bithiazoles.

A Pd(0)-catalyzed double C-N coupling of 5,5'-dibromo-2,2'-bithiazoles with (het)arylamines and subsequent in situ Ag2O-mediated oxidation provides access to cross-conjugated quinoidal 5,5'-diarylimino-2,2'-bithiazoles in moderate to high yield. The highly colored quinoidal 2,2'-bithiazoles were studied by UV/vis spectroscopy, cyclic voltammetry and computational methods.