Conclusion
In summary, TsDPEN-functionalized copolymers (PCP-TsDPEN) with the features of superhydrophobicity, high surface area, large pore volume, abundant mesoporosity, good thermal stability, and obvious chirality have been successfully synthesized from WYE-132 copolymerization of divinylbenzene with V-TsDPEN ligands. After coordination of Ru species, the PCP-TsDPEN-Ru catalysts show superior performance in ATH reactions using water as green solvent. The enrichment of the reactant in the catalyst and the product transfer from the catalyst to the water phase in the reaction system would be responsible for the superior catalytic performance. This feature should be potentially important for designing and preparing novel catalysts for organic synthesis in the future.
Experimental
Catalysts preparation
Synthesis of p-styrenesulfonyl chloride
p-styrenesulfonyl chloride was synthesized according to the literature [10]. As a excretory system typical run, 15 g of sodium p-styrenesulfonate was dissolved in 80 mL of anhydrous DMF (dried over CaH2) under N2 and cooled to 0 °C, followed by addition of 30 mL of SOCl2. After stirred at 0 °C for 30 min, the mixture was stirred at room temperature for another hour, and then poured into ice. The resulting aqueous layer was extracted with diethyl ether. Finally, the collected organic phase was combined, dried over MgSO4 and evaporated to obtain a light yellow liquid, which was p-styrenesulfonyl chloride.
In summary, TsDPEN-functionalized copolymers (PCP-TsDPEN) with the features of superhydrophobicity, high surface area, large pore volume, abundant mesoporosity, good thermal stability, and obvious chirality have been successfully synthesized from WYE-132 copolymerization of divinylbenzene with V-TsDPEN ligands. After coordination of Ru species, the PCP-TsDPEN-Ru catalysts show superior performance in ATH reactions using water as green solvent. The enrichment of the reactant in the catalyst and the product transfer from the catalyst to the water phase in the reaction system would be responsible for the superior catalytic performance. This feature should be potentially important for designing and preparing novel catalysts for organic synthesis in the future.
Experimental
Catalysts preparation
Synthesis of p-styrenesulfonyl chloride
p-styrenesulfonyl chloride was synthesized according to the literature [10]. As a excretory system typical run, 15 g of sodium p-styrenesulfonate was dissolved in 80 mL of anhydrous DMF (dried over CaH2) under N2 and cooled to 0 °C, followed by addition of 30 mL of SOCl2. After stirred at 0 °C for 30 min, the mixture was stirred at room temperature for another hour, and then poured into ice. The resulting aqueous layer was extracted with diethyl ether. Finally, the collected organic phase was combined, dried over MgSO4 and evaporated to obtain a light yellow liquid, which was p-styrenesulfonyl chloride.