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Heterogeneous High-Loading Hyperbranched Polyglycidol with Peripheral NHC–Pd Complex: Synthesis and Application as Catalyst in Suzuki Coupling Reaction

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Abstract

A new polymer-supported highly functionalized dendritic polyether with peripheral NHC–Pd complex was developed by the simple anionic ring opening polymerization of glycidol on bis(3-hydroxypropyl) amine grafted Merrifield resin and its subsequent functional modification of hydroxyl group to NHC–Pd complex. The polymeric material had high stability and swelling capacity in a wide range of solvents, even in water. Similar to supported higher generation dendrimer, the newly developed system showed high palladium content with uniformly distributed and well isolated metal nanocentres. The palladium content was found to be 2.02 mmol/g which was comparatively higher than other heterogeneous NHC–Pd based catalysts and the polymer was used as heterogeneous palladium catalyst for Suzuki coupling reaction. Various factors affecting the catalyst’s performance were studied. The high availability and increased accessibility of catalytic sites, stability and dendrimer like property of the polymeric support, reusability, better resistance to metal leaching, easy synthesis etc. are the important features of this newly synthesized catalytic system.

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References

  1. Bhagiyalakshmi M, Park SD, Cha WS, Jang HT (2010) Appl Surf Sci 256:6660

    Article  CAS  Google Scholar 

  2. Wang X, Gao H (2017) Polymers 9:188

    Article  CAS  PubMed Central  Google Scholar 

  3. Hirao A, Yoo HS (2011) Polym J 43:2

    Article  CAS  Google Scholar 

  4. Schüll C, Frey H (2012) ACS Macro Lett 1:461

    Article  CAS  Google Scholar 

  5. Gao C, Yan D (2004) Prog Polym Sci 29:183

    Article  CAS  Google Scholar 

  6. Voit BI, Lederer A (2009) Chem Rev 109:5924

    Article  CAS  PubMed  Google Scholar 

  7. Wilms D, Stiriba S, Frey H (2010) Acc Chem Res 43:129

    Article  CAS  PubMed  Google Scholar 

  8. Oikawa Y, Lee S, Kim DH, Kang DH, Kim BS, Saito K, Sasaki S, Oishi Y, Shibasaki Y (2013) Biomacromol 14:2171

    Article  CAS  Google Scholar 

  9. Turk H, Haag R, Alban S (2004) Bioconjugate Chem 15:162

    Article  CAS  Google Scholar 

  10. Kainthan RK, Janzen J, Levin E, Devin DV, Brooks DE (2006) Biomacromol 7:703

    Article  CAS  Google Scholar 

  11. Frey H, Haag R (2002) Rev Mol Biotechnol 90:257

    Article  CAS  Google Scholar 

  12. Siegers C, Biesalski M, Haag R (2004) Chem Eur J 10:2831

    Article  CAS  PubMed  Google Scholar 

  13. Venkatakrishnan S, Thengarai V, Keilitz J, Haag R (2014) Inorg Chim Acta 409:179

    Article  CAS  Google Scholar 

  14. Ferruti P, Knobloch S, Ranucci E, Duncan R, Gianasi E (1998) Macromol. Chem Phys 199:2565

    CAS  Google Scholar 

  15. Wroblewski S, Kopeckova J (1998) Macromol Chem Phys 199:2601

    Article  CAS  Google Scholar 

  16. Mammen M, Choi SK, Whitesides GM (1998) Angew Chem Int Ed 37:2754

    Article  Google Scholar 

  17. Li H, Jo JK, Zhang LD, Ha CS, Suh H, Kim I (2010) Langmuir 23:18442

    Article  CAS  Google Scholar 

  18. Pecchioli T, Kumar MM, Haag R, Christmann M (2015) Beilstein J Org Chem 11:730

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  19. Berkessel A, Kramer J, Mummy F, Neudçrfl JM, Haag R (2013) Angew Chem Int Ed 52:739

    Article  CAS  Google Scholar 

  20. Hebel A, Haag R (2002) J Org Chem 67:9452

    Article  CAS  PubMed  Google Scholar 

  21. King ASH, Twyman LJ (2002) J Chem Soc 1:2209

    Google Scholar 

  22. Schüll C, Frey H (2013) Polymer 54:5443

    Article  CAS  Google Scholar 

  23. Roller S, Turk H, Stumbe JF, Rapp W, Haag R (2006) J Comb Chem 8:350

    Article  CAS  PubMed  Google Scholar 

  24. Dong Z, Ye Z (2015) Appl Catal A 489:61

    Article  CAS  Google Scholar 

  25. Murugan E, Shanmugam P (2016) J Nanosci Nanotechnol 16(1):426

    Article  CAS  PubMed  Google Scholar 

  26. Rezaei SJT, Shamseddin A, Ramazani A, Malekzadeh AM, Asiabi PA (2017) Appl Organomet Chem 31:e3707

    Article  CAS  Google Scholar 

  27. He Y, Cai C (2011) Chem Commun 47:12319

    Article  CAS  Google Scholar 

  28. Tamami B, Nezhad MM, Ghasemi S, Farjadian F (2016) Phosphorus, Sulfur Silicon Relat Elem 191:123

    Article  CAS  Google Scholar 

  29. He Y, Lv MF, Cai C (2012) Dalton Trans 41:12428

    Article  CAS  PubMed  Google Scholar 

  30. Schwarz J, Böhm VPW, Gardiner MG, Grosche M, Herrmann WA, Hieringer W, Raudaschl-Sieber G (2000) Chem Eur J 6:1773

    Article  CAS  PubMed  Google Scholar 

  31. Díez-González S, Marion N, Nolan SP (2009) Chem Rev 109:3612

    Article  CAS  PubMed  Google Scholar 

  32. Peris E, Loch JA, Mata J, Crabtree RH (2001) Chem Commun. https://doi.org/10.1039/B008038L

    Article  Google Scholar 

  33. Kang T, Feng Q, Luo M (2005) Synlett 15:2305

    Google Scholar 

  34. Lázaro G, Fernández-Alvarez FJ, Iglesias M, Horna C, Vispe E, Sancho R, Lahoz FJ, Iglesias M, Pérez-Torrente JJ, Oro LA (2014) Catal Sci Technol 4:62

    Article  Google Scholar 

  35. Byun JW, Lee YS (2004) Tetrahedron Lett 45:1837

    Article  CAS  Google Scholar 

  36. Kim JH, Jun BH, Byun JW, Lee YS (2004) Tetrahedron Lett 45:5827

    Article  CAS  Google Scholar 

  37. Kim JW, Kim JH, Lee DH, Lee YS (2006) Tetrahedron Lett 47:4745

    Article  CAS  Google Scholar 

  38. Jadhav SN, Kumbhar AS, Mali SS, Hongc CK, Salunkhe RS (2015) New J Chem 39:2333

    Article  CAS  Google Scholar 

  39. Ranganath KVS, Onitsuka S, Kiran Kumar A, Inanaga J (2013) Catal. Sci Technol 3:2161

    CAS  Google Scholar 

  40. Rostamnia S, Hossieni HG, Doustkhah E (2015) J Organomet Chem 791:18

    Article  CAS  Google Scholar 

  41. Haag R, Sunder A, Stumbe JF (2000) J Am Chem Soc 122:2954

    Article  CAS  Google Scholar 

  42. Jisha KA, Sreekumar K (2017) Catal Lett 147:964

    Article  CAS  Google Scholar 

  43. Siyad MA, Nair ASV, Kumar GSV (2010) J Comb Chem 12:298

    Article  CAS  PubMed  Google Scholar 

  44. Wang X, Hu P, Xue F, Wei Y (2014) Carbohydr Polym 114:476

    Article  CAS  PubMed  Google Scholar 

  45. Meise M, Haag R (2008) Chemsuschem 1:637

    Article  CAS  PubMed  Google Scholar 

  46. Kale D, Rashinkar G, Kumbhar A, Salunkhe R (2017) React Funct Polym 116:9

    Article  CAS  Google Scholar 

  47. Rajesh KG, Sreekumar K (2010) Soft Mater 2:114

    Google Scholar 

  48. Bukhryakov KV, Mugemana C, Vu KB, Rodionov VO (2015) Org Lett 17:4826

    Article  CAS  PubMed  Google Scholar 

Download references

Acknowledgements

The authors gratefully acknowledge STIC-CUSAT, IISc- Bangalore, and NCESS-TVM, for the assistance in various spectral analysis. One of the authors (K. J. A) acknowledges the CSIR, Govt. of India for financial assistance.

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  1. Department of Applied Chemistry, Cochin University of Science and Technology, Kochi, Kerala, 682022, India

    J. K. Anjali & K. Sreekumar

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  1. J. K. Anjali
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  2. K. Sreekumar
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Correspondence to K. Sreekumar.

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Anjali, J.K., Sreekumar, K. Heterogeneous High-Loading Hyperbranched Polyglycidol with Peripheral NHC–Pd Complex: Synthesis and Application as Catalyst in Suzuki Coupling Reaction. Catal Lett 149, 1952–1964 (2019). https://doi.org/10.1007/s10562-019-02784-w

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