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Anchored [RuCl2(p-cymene)]2 in hybrid zirconium phosphate–phosphonate coated and pillared with double-stranded hydrophobic linear polystyrene as heterogeneous catalyst suitable for aqueous asymmetric transfer hydrogenation
A novel type of phosphonate-containing polystyrene copolymers 1a–e bearing an N′-alkylated TsDPEN chiral ligand and double-stranded polystyrene chains were prepared for the first time using simple radical copolymerization of 1-phosphonate styrene with (R,R)-N′-4′-vinylbenzyl-N-4-vinylbenzenesulfonyl-1,2-diphenylethylene-1,2-diamine. Through the coprecipitation of their supported Ru polystyrene copolymers 2a–e and NaH2PO4 with ZrOCl2, pillared hybrid zirconium phosphate–phosphonate-anchored Ru catalysts 3a–e and 4d1–d5 were obtained as heterogeneous catalysts suitable for aqueous asymmetric transfer hydrogenation. In the aqueous asymmetric transfer hydrogenation of aromatic ketones, the anchored Ru catalysts showed good catalytic activities, chemoselectivities (100%), and enantioselectivities (73.6% ee to 95.6% ee). The Ru catalysts retained their catalytic properties even at the fifth recycle time (92.2% conv., 92.1% ee). However, corresponding supported Ru catalyst 3d′ resulted in disappointing reusability because of the loss of ruthenium in every recycle process. The conversions of aromatic ketones were closely related to the o-, m- or p-positions of the substituents on the aromatic ring caused by shape-selective matching.
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