Bipyrrole units often occur in biologically significant and materials-relevant compounds. The current synthetic routes to afford these compounds suffer from harsh reaction conditions and/or tedious synthetic steps. Herein, a two-step approach for assembling substituted bipyrroles starting from 1,3-diyne and N-benzyl azomethine ylide has been demonstrated. In the first step, tungsten catalyzed twofold 1,3-dipolar cycloaddition gave rise to a range of tetrahydrobipyrroles with broad substrate scope. In the second step, selective tetrahydrobipyrroles smoothly underwent copper-catalyzed dehydrogenative aromatization through sp3 C-H functionalization to provide bipyrroles. In addition, synthetic utilization and preliminary mechanistic studies were also performed. These bipyrroles might have potential utility in drug discovery and material science.

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