Palladium-catalyzed decarboxylative heterocyclizations of [60]fullerene: preparation of novel vinyl-substituted [60]fullerene-fused tetrahydrofurans/pyrans/quinolines

Abstract

A general and practical methodology for the preparation of novel vinyl-substituted [60]fullerene-fused tetrahydrofurans/pyrans/quinolines through palladium-catalyzed decarboxylative heterocyclizations of [60]fullerene with vinylethylene/2-alkylidenetrimethylene carbonates and vinyl carbamates was developed. Without additives or ligands, the Pd(PPh3)4-catalyzed transformations undergo decarboxylative O- and N-heteroannulation processes to efficiently furnish structurally diverse [60]fullerene-fused heterocyclic derivatives.