An immobilization of copper(I) in organic-inorganic hybrid materials catalyzed Sonogashira coupling reaction was developed. Terminal alkynes reacted with aryl iodides and aryl bromides in the presence of 3-(2-aminoethylamino)propyl functionalized silica gel immobilized copper(I) catalyst, triphenylphosphine and potassium carbonate in DMF. The reactions generated the corresponding cross-coupling products in good to excellent yields. Furthermore, silica-supported copper was recovered and recycled by a simple filtration of the reaction solution and used for six consecutive trials without decreases in activity.
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Wang et al. (2006) studied this question.