Development of efficient solid chiral catalysts with designable linkage for asymmetric transfer hydrogenation of quinoline derivatives

Developing chiral solid catalysts for asymmetric catalysis is desirable for the elimination of homogeneous catalysis flaws but remains an immense challenge. Herein, we report the immobilization of TsDPEN on SBA-15 with an ionic liquid (IL) linkage via the one-pot reaction of imidazole-TsDPEN-N-Boc with 3-(trimethoxysilyl)propyl bromide in the SBA-15 mesopores. After coordination to Rh, the chiral solid catalysts could efficiently catalyze quinoline transfer hydrogenation, achieving 97% conversion with 93% ee, which was comparable to their homogeneous counterparts. The chiral solid catalyst with the IL linkage afforded much higher turnover frequency than that without the IL linkage (93 h(-1) vs. 33 h(-1)), attributed to the phase transfer and formate-enriching ability of the IL linkage. Furthermore, the effect of the pH on the reaction rate of the solid catalyst was investigated, preventing reaction rate retardation during the catalytic process. The tuning of the linkage group is an efficient approach for catalytic activity improvement of immobilized chiral catalysts. (C) 2021, Dalian Institute of Chemical Physics, Chinese Academy of Sciences. Published by Elsevier B.V. All rights reserved.

Automated summary

Developing chiral solid catalysts for asymmetric catalysis to overcome homogeneous catalysis drawbacks is a significant challenge. In this study, the immobilization of TsDPEN on SBA-15 with an ionic liquid linkage improved the catalytic performance of chiral solid catalysts, achieving high conversion and selectivity.