In this work, we report the efficient, high stable copper(II) complexes intercalated graphene oxide (GO) used as green catalysts for copper(II) complex mediated click reaction. Copper(II) Bis(2,2′‐bipyridine) [CuII (bpy)2] (C1) and Copper(II) Bis(1,10‐phenanthroline) [CuII (phen)2] (C2) have synthesized for the intercalation of corresponding nanocomposites with GO, [GO@CuII (bpy)2] (GO‐C1) and [GO@CuII (phen)2] (GO‐C2). The noncovalent interaction of complexes supported on the surface of the GO nanosheets proves as an evident active site to facilitate the enhanced catalytic activity of copper‐catalyzed alkyne azide cycloaddition (CuIIAAC) reaction for the isolation of 1,4‐disubstituted‐1,2,3‐triazoles as click products in shorter reaction time with 80%–91% yield (five examples). The X‐ray diffraction (XRD) pattern of these composites shows the enhanced interlayers d‐spacing range of 1.01–1.12 nm due to the intercalation of copper(II) complexes in between the GO basal planes and characterized by X‐ray photoelectron spectroscopy (XPS), Fourier‐transform infrared spectroscopy (FT‐IR), Raman, UV, scanning electron microscope (SEM), and thermogravimetric analysis (TGA). The as‐prepared nanocomposites were employed for the typical click reactions using the substrates of azide and acetylene. These classes of composite materials can be referred to recyclable, heterogeneous, green catalysts with high atom economy and could also be used for the isolation of click products in biomolecules.
We report the class of tetraaza coordinated copper(II) complexes of 1,10‐phenanthroline ([CuII(L1)2]ClO4), 2,2’‐bipyridine ([CuII(L2)2]ClO4) and 1,4,7,10‐tetraazacyclo‐dodecane ([CuII(L3)](ClO4)2) are employed as efficient catalysts for the Copper Catalyzed Azide Acetylene Cycloaddition (CuIIAAC) reaction. The complex [CuII(L1)2]ClO4 showed high catalytic activity with the reductant for [3+2] Huisgen cycloaddition of terminal alkyne and various azides due to its structural orientation. The corresponding 1,4‐disubstituted‐1,2,3‐triazoles are isolated in good yield (12 examples) at room temperature without the impact of additives. These complexes also facilitate the stabilization of in‐situ generated Cu(I)L species to a greater extent due to their ligand framework.
We report stable and heterogeneous graphene oxide (GO)–intercalated copper as an efficient catalyst for the organic transformations in green solvents. The GO-intercalated copper(II) complex of bis(1,4,7,10-tetraazacyclododecane) [Cu(II)-bis-cyclen] was prepared by a facile synthetic approach with a high dilution technique. The as-prepared GO-Cu(II)-bis-cyclen nanocomposite was used as a click catalyst for the 1,3 dipolar Huisgen cycloaddition reaction of terminal alkyne and azide substrates. On directing a great deal of attention toward the feasibility of the rapid electron transfer rate of the catalyst in proliferating the yield of 1,2,3-triazole products, the click catalyst GO-Cu(II)-bis-cyclen nanocomposite was designed and synthesized via non-covalent functionalization. The presence of a higher coordination site in an efficient 2D nanocomposite promotes the stabilization of Cu(I) L-acetylide intermediate during the catalytic cycle initiated by the addition of reductants. From the XRD analysis, the enhancement in the d-interlayer spacing of 1.04 nm was observed due to the intercalation of the Cu(II)-bis-cyclen complex in between the GO basal planes. It was also characterized by XPS, FT-IR, RAMAN, UV, SEM, AFM, and TGA techniques. The recyclability of the heterogeneous catalyst [GO-Cu(II)-cyclen] with the solvent effect has also been studied. This class of GO-Cu(II)-bis-cyclen nanocomposite paves the way for bioconjugation of macromolecules through the click chemistry approach.
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