Synthesis of Fullerotetrahydroquinolines via [4 + 2] Cycloaddition Reaction of [60]Fullerene with in Situ Generated Aza-o-quinone Methides.

An efficient [4 + 2] cycloaddition reaction of [60]fullerene with the in situ generated aza-o-quinone methides from N-(o-chloromethyl)aryl sulfonamides with the assistance of Cu2O has been developed to afford a series of fullerotetrahydroquinolines. This strategy exhibits a broad substrate scope and excellent functional group tolerance. A tentative reaction pathway for the formation of fullerotetrahydroquinolines is proposed on the basis of the experimental results.