Solvent-promoted catalyst-free regioselective <i>N</i>-incorporation multicomponent domino reaction: rapid assembly of π-functionalized [60]fullerene-fused dihydrocarbolines

Abstract

Described here is the first example of solvent-promoted catalyst-free N-incorporation multicomponent domino reaction for the direct construction of novel π-extension [60]fullerene-fused dihydrocarbolines from simple hydrocarbons. This unprecedented transformation is proposed to proceed by a sequential N-incorporation/[4+2] cycloaddition/elimination process, involving multiple types of bond cleavage and formation in a single chemical operation. Mechanistic studies uncover that solvent is crucial for the success of the transformation, and multiple solvent-aided deprotonation and proton transfer are involved as key steps.