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Fabrication of Nanoreactors Based on End-Functionalized Polymethacrylate and Their Catalysis Application

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Abstract

Polymer-based nanoreactor, which can be achieved by self-assembling of amphiphilic polymers in water, has attracted more and more attention in recent years. In this study, a kind of Pd-nanoreactor was fabricated by self-assembling of chiral palladium complex-containing amphiphilic polymers in water. Firstly, chain transfer reagent (CTA) CEPA-PyOx was obtained by condensation reaction of (S,S)-4-hydroxymethyl-5-phenyl-2-(2′-pyridinyl)-1,2-oxazoline (PyOx) and 4-cyano-4-[((ethylthio)carbonothioyl)thio] pentanoic acid (CEPA) in the presence of EDC·HCl. Next, polymethacrylate with a terminal chiral oxazoline ligand (CEPA-POEGMA36-PyOx) was synthesized through Reversible Addition-Fragmentation Chain Transfer (RAFT) polymerization. After removal of the thioester bond and coordination with palladium trifluoroacetate, the polymer self-assembled in water affording Pd-nanoreactor, which possess core-shell structure and with chiral palladium complex in the core. At last, the nanoreactor was successfully applied in the asymmetric catalytic synthesis of flavanone in aqueous phase, and the catalyst loading was greatly reduced compared to unsupported palladium complex. In the presence of low palladium loading (0.5 mol%), flavanone was successfully synthesized with excellent yield (98%) and high enantioselectivity (82%).

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Acknowledgements

The authors appreciate the financial support to this research by the Zhejiang Provincial Natural Science Foundation of China (No. LY17B020013) and the Fundamental Research Funds of Zhejiang Sci-Tech University (No. 2019Q020).

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Authors and Affiliations

  1. College of Textile Science and Engineering, Eco-Dyeing and Finishing Engineering Research Center, Ministry of Education, National Base for International Science and Technology Cooperation in Textiles and Consumer-Goods Chemistry, Zhejiang Sci-Tech University, Hangzhou, 310018, Zhejiang, China

    Lei Zhou, Jiaqi Qiu, Maolin Wang, Zhenkai Xu & Tao Chen

  2. College of Textile and Fashion, Shanghai University Of Engineering Science, Shanghai, 201620, China

    Jiping Wang

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  1. Lei Zhou
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  2. Jiaqi Qiu
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  3. Maolin Wang
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  4. Zhenkai Xu
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  6. Tao Chen
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Correspondence to Jiping Wang or Tao Chen.

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Zhou, L., Qiu, J., Wang, M. et al. Fabrication of Nanoreactors Based on End-Functionalized Polymethacrylate and Their Catalysis Application. J Inorg Organomet Polym 30, 4569–4577 (2020). https://doi.org/10.1007/s10904-020-01599-2

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  • DOI: https://doi.org/10.1007/s10904-020-01599-2

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