4.8 Article

Hyper-Crosslinked Porous Chiral Phosphoric Acids: Robust Solid Organocatalysts for Asymmetric Dearomatization Reactions

Journal

ACS CATALYSIS
Volume 12, Issue 8, Pages 4545-4553

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acscatal.2c00397

Keywords

chiral phosphoric acid; dearomatization; direct knitting; hyper-crosslinked; porous organocatalyst

Funding

  1. National Key R&D Program of China [2021YFA1500100]
  2. NSFC [21821002, 22031012]
  3. Science and Technology Commission of Shanghai Municipality [19590750400, 21520780100]

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Knitting rigid aromatic building blocks using external crosslinkers has become an effective strategy for synthesizing porous polymers. In this study, porous chiral phosphoric acids were synthesized using this strategy, and they were found to enable highly enantioselective dearomatization reactions. These hyper-crosslinked porous chiral phosphoric acids exhibit high reactivity, selectivity, stability, and recyclability, which are significant for practical catalyst design.
Knitting rigid aromatic building blocks using external crosslinkers has been developed into an effective strategy for thesynthesis of porous polymers in recent years. Here, we report the synthesis of porous chiral phosphoric acids by this strategy.Moreover, these porous chiral phosphoric acids were found to enable highly enantioselective dearomatization reactions. Remarkably,after being reused for 10 runs, no obvious loss in catalytic activity and selectivity was observed. The features of high reactivity,selectivity, stability, and recyclability of these hyper-crosslinked porous chiral phosphoric acids are significant for practical catalystdesign.

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