Catalytic divergent synthesis of imidazoles reaction condition-dependent [3 + 2] cyclization of TosMIC

A base-catalyzed divergent synthesis of multisubstituted imidazoles through TosMIC-based [3 + 2] cyclization reaction has been developed. In the presence of ketenimines and t BuONa, 1,4,5-trisubstituted imidazoles were obtained. Nonetheless, in the absence of ketenimines, 1,4-disubstituted imidazole was produced through cyclodimerization of TosMIC. A base-catalyzed divergent synthesis of 1,4,5-trisubstituted or 1,4-disubstituted imidazoles through TosMIC-based [3 + 2] cyclization reaction has been developed.