Palladium-catalyzed domino spirocyclization of [60]fullerene: synthesis of diverse [60]fullerene-fused spiro[4,5]/[5,5] derivatives

Abstract

Herein a new, general and practical method for the spirocyclization of [60]fullerene through a palladium-catalyzed domino Heck/C–H activation reaction is presented. A wide range of novel [60]fullerene-fused spirocyclic derivatives can be easily and flexibly synthesized with a broad substrate scope and excellent functional-group tolerance. A plausible mechanism involving an alkyl Pd(II) species as a key intermediate has been proposed.