Bifunctional Graphene-Based Metal-Free Catalysts for Oxidative Coupling of Amines.

Graphene oxide (GO), an emerging material ornamented with oxygen-containing functional groups, is becoming a promising alternative for various applications. The piranha solution treatment of GO can increase oxygen-containing functional groups and result in improved graphene oxide (IGO), as well as restore the functional groups lost because of the reaction. It is found that GO can oxidize the amine to the corresponding imine in the absence of oxygen and a catalyst, and the obtained IGO even shows higher activity. In addition, the piranha solution can partially restore the reactivity of GO after the reaction. The different roles of oxygen-containing functional groups in the oxidative coupling reaction are investigated. A possible reaction mechanism for the oxidation of benzylamine to N-benzylidene benzylamine is also proposed.