Synthesis of the 3,3′-bipyrrole scaffold from diyne

-benzyl azomethine ylide has been demonstrated. In the first step, tungsten catalyzed twofold 1,3-dipolar cycloaddition gave rise to tetrahydrobipyrrole products in 42-85% yields. In the second step, a range of tetrahydrobipyrroles smoothly underwent copper-catalyzed dehydrogenative aromatization and provided 3,3'-bipyrroles in 54-80% yields. In addition, synthetic utilization and preliminary mechanistic studies were also performed. These bipyrroles might have potential utility in drug discovery and materials science.