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Organoamine-functionalized graphene oxide as a bifunctional carbocatalyst with remarkable acceleration in a one-pot
Fang Zhang1, Huangyong Jiang, Xiaotao Wu
1The Education Ministry Key Lab of Resource Chemistry and Shanghai Key Laboratory of Rare Earth Functional Materials, Shanghai Normal University , Shanghai 200234, P. R. China.
Abstract:
In this work, we reported the synthesis of bifunctional carbocatalyst with acid-base dual-activation mechanism by introducing organoamines on the basal planes of graphene oxide (GO). Interestingly, GO-supported primary amine (AP-GO) exclusively promoted one-pot Henry-Michael reactions with excellent activity to give synthetically valuable multifunctionalized nitroalkanes. Notably, it also exhibited significantly higher activity than those using propylamine, activated carbon-supported primary amine, and mesoporous silica-supported primary amine as the catalysts. This superior catalytic performance originated from the unique properties of AP-GO, which provided the acid-base cooperative effect by the appropriate positioning of primary amines on their basal planes and carboxyl acids along their edges and the decreased diffusion resistance of the reactants and the intermediates during the multistep catalytic cycles because of its open two-dimensional sheet-like structure. Moreover, it could be readily recycled by simple filtration and subsequently reused without significant loss of its catalytic activity in a six times run test.
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