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Keywords:

  • cascade cyclization;
  • heteroarenes;
  • iridium;
  • vinyl radicals;
  • visible-light photocatalysis

Abstract

Thumbnail image of graphical abstract

Vinyl radicals were generated from α-bromochalcones or α-bromocinnamate ethyl ester under visible light photoredox catalyzed conditions via an oxidative quenching cycle of the iridium complex [Ir{dF(CF3)ppy}2(dtbbpy)]PF6 and subjected to cascade cyclizations with heteroarenes entailing two consecutive C[BOND]C bond formations and three C[BOND]H activations. The process is amenable to furans, benzofurans, pyrroles, and indoles, giving rise to a broad variety of novel polycyclic frameworks in high yields under mild and environmentally benign reaction conditions.