Divergent reactivity of α-azidochalcones with metal β-diketonates: tunable synthesis of substituted pyrroles and indoles

Abstract

A divergent reactivity of α-azidochalcones with metal β-diketonates for the synthesis of substituted pyrroles and indoles is described. Metal β-diketonates have been applied as bifunctional reactive partners. With a copper complex, the synthesis of substituted pyrroles in micellar media via 2H-azirine intermediates has been achieved under mild conditions, while with Fe(acac)₂ as a catalyst, the reaction proceeds smoothly to yield indoles regioselectively.