Synthesis of [60]Fullerene-Fused Spiroindanes by Palladium-Catalyzed Oxidative Annulation of [60]Fullerene with 2-Aryl Cyclic 1,3-Dicarbonyl Compounds

Abstract

A convenient and facile palladium-catalyzed reaction of [60]fullerene (C60) with 2-aryl cyclic 1,3-dicarbonyl compounds via the enolate-directed sp(2) C-H activation and sp(3) C-H functionalization has been exploited to synthesize the novel and rare C60-fused spiroindanes for the first time. This reaction is easy to perform with broad substrate scope and provides diversified products in 20-50% yields. A plausible reaction mechanism involving the palladium-catalyzed enolate-directed C-H activation and subsequent cyclization has been proposed, and the electrochemistry of the C60-fused spiroindanes has also been investigated.