A new Cu-anchored mesoporous organosilica material for facile C–S coupling reactions under microwave irradiation

• Synthesis of Cu-anchored 2D-hexagonally ordered functionalized mesoporous silica.
• 3-(2-Aminoethylamino) propyl-dimethoxymethyl grafted SBA-15 showing D2 species in 29Si NMR.
• One-pot three-component C–S cross-coupling reactions for the synthesis of thioethers.
• Microwave assisted heating for fast and convenient C–S coupling reactions.

We report a new ordered Cu-anchored 2D-hexagonal mesoporous imine functionalized organosilica material Cu-MPIOS. This Cu-anchored mesoporous material has been synthesized via post synthetic functionalization of SBA-15 with 3-(2-aminoethylamino)propyl-dimethoxymethylsilane followed by Schiff-base condensation with 2-thiophene carboxaldehyde. Cu(I) has been grafted finally over Schiff-base functionalized mesoporous material through chemical impregnation to obtain Cu-MPIOS. The materials are characterized thoroughly using various techniques like powder X-ray diffraction, N2 adsorption/desorption analysis, FTIR, UV–vis spectroscopy, FEG-TEM, FE-SEM, 13C cross-polarization magic angle spinning NMR, TGA/DTA, EPR, AAS and CHN chemical analysis. High Brunauer–Emmett–Teller (BET) surface area and the presence of very large size mesopores (8.1 nm) in Cu-MPIOS has motivated us to explore its catalytic activity in one-pot three-component C–S cross coupling reaction by varying different aryl halides in the aqueous medium under microwave assisted heating conditions. This heterogeneous Cu-catalyst shows high catalytic performance as well as good recycling efficiency in this C–S coupling reaction, suggesting its future potential for the synthesis of value added thioether derivatives.

Cu-grafted functionalized SBA-15 material has been synthesized via post-synthesis functionalization of SBA-15 and it showed excellent catalytic activity for the synthesis of thioether derivatives via one-pot three component C–S coupling reactions.Figure optionsDownload high-quality image (144 K)Download as PowerPoint slide