Development of a Graphene Oxide-Supported N-Heterocyclic Carbene Copper(I) Complex as a Heterogeneous Catalyst for the Selective N-Monoalkylation of Amines

A new N-heterocyclic carbene (NHC) copper(I) complex supported on graphene oxide (GO-NHC-Cu) was synthesised and thoroughly characterised by various instrumental techniques such as FT-IR, FT-Raman, PXRD, XPS, FESEM, EDX, HRTEM, TGA and ICP-OES. The catalytic activity of the supported complex was explored in the N-alkylation of anilines with alcohols under solvent-free and aerobic conditions to afford monoalkylated products in good to excellent yields (20 products, 83-96%). All products were isolated and characterised by H-1 and C-13{H-1} NMR spectroscopy. The catalyst was recuperated from the reaction mixture by simple filtration and reused for up to five successive cycles with insignificant loss in the catalytic activity. The control experiments showed that the reaction proceeded in aerobic conditions. The green chemistry metrics for the reaction were found to be fairly close to the ideal values: carbon efficiency (95.9%), E-factor (0.15), atom economy (92.14%), process mass intensity (1.15) and reaction mass efficiency (86.80%). The air stability, selectivity, recyclability of the catalyst, and the high yields of the products under solvent-free conditions are some of the salient features of the reported methodology.

Automated summary

A new N-heterocyclic carbene (NHC) copper(I) complex supported on graphene oxide (GO-NHC-Cu) was synthesized and successfully used as a catalyst for the N-alkylation of anilines with alcohols under solvent-free and aerobic conditions, showing high catalytic activity and yields. The methodology is simple, green and efficient.