Synthesis Of MCM-41-supported Copper Complexes And Their Applications In Carbon-carbon And Carbon-sulfur Bonds Formation Reactions

1. MCM-41-supported Schiff base-pyridine bidentate nitrogen copper(I)complex [MCM-41-Sb,Py-CuI] was prepared from commercially available3-aminopropyl-triethoxysilane via immobilization on MCM-41, followed by reactingwith pyridine-2-carboxaldehyde and copper iodide. This supported copper catalystwas characterized by XRD, ICP and elemental analysis. We investigated Sonogashirareaction of aryl iodides with terminal alkynes catalyzed by the MCM-41-Sb,Py-CuIcomplex. It was found that the Sonogashira reaction of aryl iodides with terminalalkynes proceeded smoothly in the presence of5mol%MCM-41-Sb,Py-CuI to givethe corresponding coupling products in excellent yields. This novel heterogeneouscopper catalyst can be easily recovered by simple filtration and reused several timeswithout significant loss of activity.2. Dinitrogen-functionalized MCM-41anchored copper(I)complex(MCM-41-2N-CuI) was conveniently prepared from commercially available3-(2-aminoethylamino)-propyltrimethoxysilane via immobilization on MCM-41,followed by reacting with cuprous iodide. The supported copper complex wascharacterized by XRD, ICP and elemental analysis. We found that this heterogeneouscopper complex exihibited good catalytic activity in the reaction of a variety of2-halobenzamide with β-keto esters, yielding the corresponding3,4-disubstitutedisoquinolin-1(2H)-one in good yields. The novel supported bidentate nitrogen coppercatalyst can be easily recovered by simple filtration and reused many times withoutobvious loss of activity.3. Trihydroxy-functionalized MCM-41anchored copper complex wasconveniently prepared from the reaction product of3-aminopropyltriethoxysilane andbenzoyl chloride-4-formaldehyde via immobilization on MCM-41, followed byreacting with trihydroxymethyl aminomethane and cuprous iodide. The supportedcopper complex was characterized by XRD, ICP and elemental analysis. Its catalyticperformance in the coupling reaction of aryl iodides and thiols was studied. We foundthat this heterogeneous copper complex catalyst exihibited high activity in thereaction of ary liodides and thiols, and it can be easily recovered by simple filtrationand reused several times without significant loss of activity.