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Merrifield resin supported ionic liquids/L-proline as effcient and recyclable catalyst systems for asymmetric aldol reaction have been developed. L -Proline with Merrifield resin supported ionic liquids can catalyze asymmetric aldol reaction smoothly and generate the corresponding products in good to excellent yields and ee values. In addition, the supported catalyst systems can be recycled simply by filtration and reused for five times without significant decrease in activity.

A novel silica-anchored proline-copper(I) organic-inorganic hybrid material as an efficient catalyst for the Sonoga-shira reaction was developed. Terminal alkynes were reacted with aryl iodides and bromides smoothly in the presence of a proline-functionalized silica-anchored copper(I) catalyst in DMF to afford the corresponding cross-coupling products in good to excellent yields. Furthermore, silica-anchored proline-copper(I) catalyst was recovered and recycled by a simple filtration of the reaction solution and reused for six times without significant decreases in activity.

The immobilization of palladium on silica gel in Heck reaction has been developed. Iodobenzenes, bromobenzenes and activated chlorobenzenes were coupled with olefins (Heck reaction) smoothly to afford the corresponding cross-coupling products in good to excellent yields under phosphine- and amine-free reaction conditions in the presence of silica gel supported palladium, Silica-Ap-Pd cat. as catalyst, potassium carbonate as base and DMF as solvent. Furthermore, the silica-supported palladium catalyst 3 could be recovered and recycled by a simple filtration of the reaction solution and used for 6 consecutive trials without significant loss of its catalytic activity.