MCM-41-immobilized Schiff base-pyridine bidentate copper(I) complex as a highly efficient and recyclable catalyst for the Sonogashira reaction

• The MCM-41-Sb,Py–CuI complex can be easily prepared by a simple procedure.
• This heterogeneous copper catalyst exhibits high activity for Sonogashira reaction.
• This copper catalyst can be reused for 10 times without any decrease in activity.
• Our catalytic system provides a practical route for the synthesis of aryl acetylenes.

A novel MCM-41-immobilized Schiff base-pyridine bidentate copper(I) complex [MCM-41-Sb,Py–CuI] was conveniently prepared from commercially available and inexpensive 3-aminopropyltriethoxysilane via immobilization on MCM-41, followed by reacting with pyridine-2-carboxaldehyde and copper(I) iodide. It was found that this heterogeneous copper complex is a highly efficient catalyst for the Sonogashira coupling of aryl halides with terminal alkynes, affording a variety of aryl acetylenes in good to excellent yields and can be recovered by a simple filtration of the reaction solution and reused for at least 10 consecutive trials without any decreases in activity.

The highly efficient heterogeneous Sonogashira coupling reaction of aryl iodides and bromides with terminal alkynes catalyzed by an MCM-41-immobilized Schiff base-pyridine bidentate copper(I) complex [MCM-41-Sb,Py–CuI] is described.Figure optionsDownload as PowerPoint slide