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Polymeric Micelles with Chiral Diamine-Ru(II) Catalysts for Asymmetric Transfer Hydrogenation of Ketones in Water

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Abstract

Chiral aromatic alcohols with unique structures have attracted wide attention in asymmetric catalysis for decades. In this study, polymeric micelles with chiral diamine-Ru(II) catalysts in the hydrophobic core for asymmetric transfer hydrogenation of ketones affording chiral aromatic alcohols were presented. Firstly, block copolymers with (1R,2R)-(+)-1,2-diphenyl ethylenediamine (DPEN) in the pendant chain were successfully synthesized by Ring-Opening Metathesis Polymerization (ROMP) using 1,1-dimethyl ethyl N-(2-amino-1,2-diphenylethyl) carbamate (NB-DPEN-Boc) and polyethylene glycol (NB-PEG2000) with norbornene groups as raw materials. The structures of block copolymers P(DPEN)-co-P(PEG2000) were characterized by FT-IR and 1H NMR. Next, Block copolymers with chiral DPEN ligand in the pendant chain coordinate with [RuCl2(p-cymene)]2 to provide amphiphilic polymers with chiral diamine-Ru(II) catalyst. Then, the self-assembly of the amphiphilic polymers in water produced the polymeric micelles with chiral diamine-Ru(II) catalysts in the hydrophobic core. The particle sizes were found to be 65 nm by DLS analysis. The polymeric micelles as catalytic nanoreactors were successfully applied in the asymmetric transfer hydrogenation (ATH) of various ketones in water. The heterogenization of homogeneous catalysts and construction of catalysts for aqueous catalysis demonstrate potential application prospects in the preparation of chiral aromatic alcohols.

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References

  1. R. Zhang, W. Liu, J. Zeng, J. Meng, H. Jiang, J. Wang, D. Xing, Eur. J. Med. Chem. 230, 114111 (2022)

    Article  CAS  PubMed  Google Scholar 

  2. M. Li, X. Lang, M. Moran Cabrera, S. De Keyser, X. Sun, N. Da Silva, I. Wheeldon, Biotechnol. Biofuels 14, 3 (2021)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  3. E. Bechthold, J.A. Schreiber, K. Lehmkuhl, B. Frehland, D. Schepmann, F.A. Bernal, C. Daniliuc, I. Álvarez, C.V. Garcia, T.J. Schmidt, G. Seebohm, B. Wünsch, J. Med. Chem. 64, 1170–1179 (2021)

    Article  CAS  PubMed  Google Scholar 

  4. K. Kodama, F. Takase, T. Hirose, RSC Adv. 11, 18162–18170 (2021)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  5. G.R. Boyce, S.F. Musolino, J. Yang, A.D. Smith, J.E. Taylor, J. Org. Chem. 87, 13367–13374 (2022)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  6. E. Şahin, Synth. Commun. 50, 549–557 (2019)

    Article  Google Scholar 

  7. Z. Yang, X. Li, G. Cai, C. Peng, Y. Zhong, X. Luo, Process Biochem. 76, 34–39 (2019)

    Article  CAS  Google Scholar 

  8. Y. Baydaş, E. Dertli, E. Şahin, Synth. Commun. 50, 1035–1045 (2020)

    Article  Google Scholar 

  9. R. Morris, S. Smith, Synthesis 47, 1775–1779 (2015)

    Article  Google Scholar 

  10. V.S. Shende, P. Singh, B.M. Bhanage, Catal. Sci. Technol. 8, 955–969 (2018)

    Article  CAS  Google Scholar 

  11. V. Bernal, A. Sevilla, M. Canovas, J.L. Iborra, Microb. Cell Fact. 6, 31 (2007)

    Article  PubMed  PubMed Central  Google Scholar 

  12. C. Ke, X. Yang, H. Rao, W. Zeng, M. Hu, Y. Tao, J. Huang, Springerplus 5, 591 (2016)

    Article  PubMed  PubMed Central  Google Scholar 

  13. A.M. Salvo, F. Giacalone, M. Gruttadauria, Molecules 21, 1288 (2016)

    Article  PubMed  PubMed Central  Google Scholar 

  14. T. Ayad, P. Phansavath, V. Ratovelomanana-Vidal, Chem. Rec. 16, 2750–2767 (2016)

    Article  CAS  PubMed  Google Scholar 

  15. A.M. Krieger, V. Sinha, G. Li, E.A. Pidko, Organometallics 41, 1829–1835 (2022)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  16. J. Margalef, T. Slagbrand, F. Tinnis, H. Adolfsson, M. Diéguez, O. Pàmies, Adv. Synth. Catal. 358, 4006–4018 (2016)

    Article  CAS  Google Scholar 

  17. V.J. Kolcsár, G. Szőllősi, ChemCatChem 14, 1501 (2021)

    Google Scholar 

  18. M. Vasiloiu, P. Gaertner, R. Zirbs, K. Bica, Eur. J. Org. Chem. 2015, 2374–2381 (2015)

    Article  CAS  Google Scholar 

  19. J.-X. Zhou, D.-Y. Zhu, J. Chen, X.-J. Zhang, M. Yan, A.S.C. Chan, Tetrahedron Lett. 65, 152792 (2021)

    Article  CAS  Google Scholar 

  20. M.S. Shukla, P.E. Hande, S. Chandra, ChemistrySelect 7, 549 (2022)

    Article  Google Scholar 

  21. R. Qu, H. Suo, Y. Gu, Y. Weng, Y. Qin, Polymers (Basel) 14, 1128 (2022)

    Article  CAS  PubMed  Google Scholar 

  22. Z. Wang, R.L. Yang, J.D. Zhu, X.X. Zhu, Sci. China Chem. 53, 1844–1852 (2010)

    Article  CAS  Google Scholar 

  23. L. Wang, X. Chen, Y. Duan, Q. Luo, D. Wang, Catal. Sci. Technol. 10, 4191–4200 (2020)

    Article  CAS  Google Scholar 

  24. N. Nath, S. Chakroborty, P. Panda, K. Pal, Top. Catal. 65, 1706–1718 (2022)

    Article  CAS  Google Scholar 

  25. R.K. Sharma, D. Rawat, J. Inorg. Organomet. Polym. 21, 619–626 (2011)

    Article  CAS  Google Scholar 

  26. T.H. Abdtawfeeq, Z.A. Farhan, K. Al-Majdi, M.A. Jawad, R.S. Zabibah, Y. Riadi, S.K. Hadrawi, A. Al-Alwany, M.A. Shams, J. Inorg. Organomet. Polym. 33, 472–483 (2022)

    Article  Google Scholar 

  27. S. Luo, Z. Zeng, G. Zeng, Z. Liu, R. Xiao, M. Chen, L. Tang, W. Tang, C. Lai, M. Cheng, B. Shao, Q. Liang, H. Wang, D. Jiang, ACS Appl. Mater. Interfaces 11, 32579–32598 (2019)

    Article  CAS  PubMed  Google Scholar 

  28. R. Tanbour, A.M. Martins, W.G. Pitt, G.A. Husseini, Curr. Pharm. Des. 22, 2796–2807 (2016)

    Article  CAS  PubMed  Google Scholar 

  29. Z. Yang, K. Fu, J. Yu, X. Liu, J. Inorg. Organomet. Polym. 29, 59–65 (2018)

    Article  Google Scholar 

  30. M. Wang, Y. Min, J. Huang, Y. Shi, X. Dong, X. Zhou, X. Yu, D. Qi, Z. Hua, T. Chen, ACS Appl. Polym. Mater. 4, 1411–1421 (2022)

    Article  CAS  Google Scholar 

  31. X. Zhu, X. Wang, X. Dong, L. Zhang, D. Qi, Z. Hua, T. Chen, J. Mol. Struct. 1285, 135482 (2023)

    Article  CAS  Google Scholar 

  32. J. Huang, X. Zhu, Y. Wang, Y. Min, X. Li, R. Zhang, D. Qi, Z. Hua, T. Chen, Polymer 255, 125173 (2022)

    Article  CAS  Google Scholar 

  33. X. Zhu, X. Wang, G. Zhou, H. Yin, D. Qi, H. Deng, T. Chen, J. Inorg. Organomet. Polym. (2023). https://doi.org/10.1007/s10904-023-02752-3

    Article  Google Scholar 

  34. L. Zhou, J.Q. Qiu, M.L. Wang, Z.K. Xu, J.P. Wang, T. Chen, J. Inorg. Organomet. Polym. 30, 4569–4577 (2020)

    Article  CAS  Google Scholar 

  35. D. Plażuk, J. Zakrzewski, M. Salmain, A. Błauż, B. Rychlik, P. Strzelczyk, A. Bujacz, G. Bujacz, Organometallics 32, 5774–5783 (2013)

    Article  Google Scholar 

  36. M. Alaboalirat, L. Qi, K.J. Arrington, S. Qian, J.K. Keum, H. Mei, K.C. Littrell, B.G. Sumpter, J.-M.Y. Carrillo, R. Verduzco, J.B. Matson, Macromolecules 52, 465–476 (2018)

    Article  Google Scholar 

  37. G. Tang, M. Chen, J. Fang, Z. Xu, H. Gong, Q. Peng, Z. Hou, Catal. Commun. 121, 43–47 (2019)

    Article  CAS  Google Scholar 

  38. I. Dragutan, V. Dragutan, P. Filip, B.C. Simionescu, A. Demonceau, Molecules 21, 198 (2016)

    Article  PubMed  PubMed Central  Google Scholar 

  39. S.I. Subnaik, C.E. Hobbs, Polym. Chem. 10, 4524–4528 (2019)

    Article  CAS  Google Scholar 

  40. D. Astruc, J. Inorg. Organomet. Polym. Mater. 30, 111–120 (2019)

    Article  Google Scholar 

  41. J.K. Su, Z. Jin, R. Zhang, G. Lu, P. Liu, Y. Xia, Angew. Chem. Int. Ed. 58, 17771–17776 (2019)

    Article  CAS  Google Scholar 

  42. D.C. Church, L. Takiguchi, J.K. Pokorski, Polym. Chem. 11, 4492–4499 (2020)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  43. I. Dragutan, V. Dragutan, H. Fischer, J. Inorg. Organomet. Polym. 18, 311–324 (2008)

    Article  CAS  Google Scholar 

  44. R. Bandari, M.R. Buchmeiser, Catal. Sci. Technol. 2, 220–226 (2012)

    Article  CAS  Google Scholar 

  45. N. Li, H. Wang, X. Qu, Y. Chen, Mar. Drugs 15, 223 (2017)

    Article  PubMed  PubMed Central  Google Scholar 

  46. X. Lin, J. Shi, S. Niwayama, RSC Adv. 13, 3494–3504 (2023)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  47. V. Athanasiou, P. Thimi, M. Liakopoulou, F. Arfara, D. Stavroulaki, I. Kyroglou, D. Skourtis, I. Stavropoulou, P. Christakopoulos, M. Kasimatis, P.G. Fragouli, H. Iatrou, Polymers-Basel 12, 2819 (2020)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  48. F. Zhong, M. Ma, Z. Zhong, X. Lin, M. Chen, Chem. Sci. 12, 1783–1790 (2020)

    Article  PubMed  PubMed Central  Google Scholar 

  49. Y. Jiang, L.-C. Cheng, Y. Xie, L.-L. Qiu, Q. Yang, H.-Y. Lu, Oncotarget 8, 3315–3326 (2017)

    Article  PubMed  Google Scholar 

  50. Z. Binkhathlan, W. Qamar, R. Ali, H. Kfoury, M. Alghonaim, Saudi Pharm. J. 25, 944–953 (2017)

    Article  PubMed  PubMed Central  Google Scholar 

Download references

Funding

The authors acknowledge the financial support from the National Natural Science Foundation of China (52273216), the Zhejiang Provincial Key Research and Development Program (2023C01094), and the Leading Talents of the Zhejiang Provincial 10000 Talents Plan for Scientific and Technological Innovation (2020R52023).

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Authors and Affiliations

  1. Zhejiang Provincial Engineering Research Center for Green and Low-Carbon Dyeing and Finishing, Zhejiang Sci-Tech University, Hangzhou, 310018, China

    Lianpei Zhou, Peipei Ji, Xiuwu Wang, Dongming Qi & Tao Chen

  2. Key Laboratory of Green Cleaning Technology and Detergent of Zhejiang Province, Lishui, 323000, China

    Dongming Qi & Tao Chen

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  1. Lianpei Zhou
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  2. Peipei Ji
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Contributions

LZ: conducting the experiments and writing the first draft. PJ and XW: participating in some experiments and data analysis. DQ: funding acquisition and co-supervision of the students. TC: funding acquisition, design of the catalyst and revision of the final manuscript. All authors agreed with the final version of the submitted manuscript.

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Correspondence to Tao Chen.

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Zhou, L., Ji, P., Wang, X. et al. Polymeric Micelles with Chiral Diamine-Ru(II) Catalysts for Asymmetric Transfer Hydrogenation of Ketones in Water. J Inorg Organomet Polym 34, 1172–1180 (2024). https://doi.org/10.1007/s10904-023-02878-4

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