Copper-Mediated Radical-Induced Ring-Opening Relay Cascade Carboannulation Reaction of [60]Fullerene with Cyclobutanone Oxime Esters: Access to [60]Fullerene-Fused Cyclopentanes.

An unexpected copper-mediated radical-induced ring-opening relay cascade carboannulation reaction of [60]fullerene with cyclobutanone oxime esters is presented for the preparation of various Cl-/Br-incorporated [60]fullerene-fused cyclopentanes. The unique relay cascade transformation uses inexpensive copper salts as promoters and halogen sources and features simple redox-neutral conditions and a broad substrate scope, providing a practical access to a class of novel five-membered carbocycle-fused fullerenes.