N-Heterocyclic Carben Catalyzed Synthesis Of [60] Fullerene-fused Cyclopentanone And [60] Fullerene-fused 2-cyclohexen-1-one

The introduction of versatile functional groups on the fullerene core can improve the solubility of fullerenes,level and electron affinity as well as other physical and chemical properties,thus expanding the application of fullerenes in the field of optoelectronic materials and biological medicine,etc.Therefore,the development of new and effective methods for creating novel fullerene derivatives is of crucial importance.In this dissertation,we developed organic small molecular N-heterocyclic carbenes-catalyzed carboannulation for the synthesis of [60]fullerene-fused cyclopentanone derivatives and [60]fullerene-fused2-cyclohexenone derivatives.We employed ?,?-unsaturated aldehydes as starting material to successfully realize the synthesis of a series of novel [60] fullerene fused cyclopentanones and 2-cyclohexenones through umpolung strategy in the presence N-heterocyclic carbine,base and oxidant.This is also the first example of cycloacylation of[60]fullerene achieved by polarity reversal strategy of aldehydes.By screening different N-heterocyclic carbines,bases and oxidants and their dosage,we explored the effect of different reaction conditions on this reaction.Under the optimal conditions,we extended a series of reaction substrates and investigated the effect of different substituents on this reaction.At the same time,the electrochemical properties of the new obtained products were investigated.The results of electrochemical properties revealed that these novel[60]fullerene derivatives are potential electron acceptor materials.This carboannulation reaction uses environmentally friendly organic small molecule catalyst,exhibits a broad substrate scope and functional group tolerance,and is also suitable for the large-scale synthesis.