Synthesis of Annulated Arenes and Heteroarenes Involving Lewis Acid-Mediated Regioselective Annulation of Unsymmetrical 1,2-(Diaryl/diheteroarylmethine)dipivalates

Abstract

A ZnBr(2)-mediated regioselective annulation of unsymmetrical 1,2-diarylmethinedipivalates in DCM at room temperature led to the formation of annulated arenes and heteroarenes. The annulation of the dipivalate proceeds through the intermediacy of benzylic carbocations followed by intramolecular cyclization and subsequent aromatization to give the annulated products. The annulation methodology is highly efficient for the syntheses of anthracene as well as naphtho[b]thiophene analogues.