Synthesis Of [60] Fullerene-fused Dihydrocarbolines Derivatives

Chemical functionalization of fullerenes is an important subject.Chemical functionalization of fullerenes can modulate their electronic and physicochemical properties,such as magnetic properties,fluorescence property,nonlinear optical performance,and lubricating property and so on.Up to now,fullerene materials play an important role in the superconductor,soft organic ferromagnet,optical materials,functional polymer material,and the biological activity material.Therefore,there is high demand to develop new and efficient methods for the synthesis of structurally diverse fullerene materials.In this dissertation,we have developed a transition-metal-free regioselective N-incorporation/annulation/elimination domino process for the synthesis of [60]fullerene-fused dihydrocarbolines under mild conditions.We explored the influence of different reaction conditions,including different nitrogen sources,acids,and solvents.Under the optimal conditions,we extended the scope of substrate,and experiment results proved that this transformation exhibited excellent functional-group tolerance and broad substrate scope.In the presence of NaNO2 and TFA,the reaction of [60]fullerene with C1-functionalized indoles efficiently delivered [60]fullerene-fused dihydrocarboline derivatives under room temperature.Simple and readily available NaNO2 serves as the nitrogen source and the oxidant in this unique transformation.The reaction is easily handled and proceeds under mild conditions.At last,the reaction mechanism was explored.