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Zwitterionic Phosphine Ligand with a Lysine Tag and its Application for Hydroformylation of 1-Octene in Ionic Liquid/MeOH System

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Abstract

Here we report a highly active and selective hydroformylation of 1-octene in ionic liquid (IL)/MeOH system based on a zwitterionic phosphine ligand bearing a lysine moiety (L(NH2)COOH). The Rh-catalyst grafted lysine in the form of ammonium salt ([Rh-L(NH3 +)COOH]Tf2N) was successfully immobilized in the IL [bmim]Tf2N and recycled for seventeen times without significant loss of activity, selectivity and Rh catalysts. This study has provided a novel strategy for efficient separation and recycling of Rh catalysts.

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References

  1. Frohning CD, Kohlpainter CW (1996) In: Cornils B, Herrmann WA (eds) Applied homogeneous catalysis with organometallic compounds, 1st edn. Wiley, Weinheim, p 29

    Google Scholar 

  2. Kuntz EG (1987) ChemTech 17:570–575

    CAS  Google Scholar 

  3. Haumann M, Riisager A (2008) Chem Rev 108:1474–1497

    Article  CAS  Google Scholar 

  4. Welton T (1999) Chem Rev 99:2071–2084

    Article  CAS  Google Scholar 

  5. Dupont J, de Souza RF, Suarez PAZ (2002) Chem Rev 102:3667–3692

    Article  CAS  Google Scholar 

  6. Pârvulescu VI, Hardacre C (2007) Chem Rev 107:2615–2665

    Article  Google Scholar 

  7. Chauvin Y, Mussmann L, Olivier H (1995) Angew Chem Int Ed 34:2698–2700

    CAS  Google Scholar 

  8. Wasserscheid P, Waffenschmidt H, Machnitzki P, Kottsieper KW, Stelzer O (2001) Chem Commun 451–452

  9. Dupont J, Silva SM, de Souza RF (2001) Catal Lett 77:131–133

    Article  CAS  Google Scholar 

  10. Webb PB, Sellin MF, Kunene TE, Williamson S (2003) Slawin AMZ J Am Chem Soc 125(15577–1558):8

    Google Scholar 

  11. Silva SM, Bronger RPJ, Freixa Z, Dupont J, van Leeuwen PWNM (2003) New J Chem 27:1294–1296

    Article  CAS  Google Scholar 

  12. Mehner CP, Cook RA, Dispenziere NC, Mozeleski EJ (2004) Polyhedron 23:2679–2688

    Article  Google Scholar 

  13. Ni B, Headley AD (2010) Chem Eur J 16:4426–4436

    Article  CAS  Google Scholar 

  14. Lombardo M, Trombini C (2010) ChemCatChem 2:135–145

    Article  CAS  Google Scholar 

  15. Šebesta R, Kmentova I, Toma Š (2008) Green Chem 10:484–496

    Article  Google Scholar 

  16. Sirieix J, Ossberger M, Betzemeier B, Knochel P (2000) Synlett 11:1613–1615

    Google Scholar 

  17. Brasse CC, Englert U, Salzer A, Waffenschmidt H, Wasserscheid P (2000) Organometallics 19:3818–3823

    Article  CAS  Google Scholar 

  18. Favre F, Olivier-Bourbigou H, Commereuc D, Saussine L (2001) Chem Commun 1360–1361

  19. Bronger RPJ, Silva SM, Kamer PCJ, van Leeuwen PWNM (2002) Chem Commun 3044–3045

  20. Lee S, Zheng YJ, Piao JY, Yoon H, Song CE, Choi JH, Hong J (2003) Chem Commun 2624–2625

  21. Yao Q, Zhang Y (2003) Angew Chem Int Ed 42:3395–3398

    Article  CAS  Google Scholar 

  22. Audic N, Clavier H, Mauduit M, Guillemin JC (2003) J Am Chem Soc 125:9248–9249

    Article  CAS  Google Scholar 

  23. Baleizão C, Gigante B, Garcia H, Corma A (2003) Tetrahedron Lett 44:6813–6816

    Article  Google Scholar 

  24. Gadenne B, Hesemann P, Moreau JJE (2005) Tetrahedron Asymmetry 16:2001–2006

    Article  CAS  Google Scholar 

  25. Doherty S, Goodrich P, Hardacre C, Knight JG, Nguyen MT, Pârvulescu VI (2007) Adv Synth Catal 349:951–963

    Article  CAS  Google Scholar 

  26. Gavrilov KN, Lyubimov SE, Bondarev OG, Maksimova MG, Zheglov SV (2007) Adv Synth Catal 349:609–616

    Article  CAS  Google Scholar 

  27. Feng X, Pugin B, Kűsters E, Sedelmeier G, Blaser HU (2007) Adv Synth Catal 349:1803–1807

    Article  CAS  Google Scholar 

  28. Doherty S, Goodrich P, Hardacre C, Pârvulescu V, Paun C (2008) Adv Synth Catal 350:295–302

    Article  CAS  Google Scholar 

  29. Šebesta R, Bilčīk F (2009) Tetrahedron Asymmetry 20:1892–1896

    Article  Google Scholar 

  30. Jin X, Xu X, Zhao K (2012) Tetrahedron Asymmetry 23:1058–1067

    Article  CAS  Google Scholar 

  31. Kuang SM, Fanwick PE, Walton RA (2002) Inorg Chim Acta 338:219–227

    Article  CAS  Google Scholar 

  32. Hoffman RV (1974) Tetrahedron Lett 28:2415–2416

    Article  Google Scholar 

  33. Krompieca S, Penkalaa M, Szczubiałkab K, Kowalska E (2012) Coord Chem Rev 256:2057–2095

    Article  Google Scholar 

Download references

Acknowledgments

We gratefully thank the financial support from National Natural Science Foundation of China (No. 20606019, 20976086), Foundation of Key Laboratory of Oil & Gas Fine Chemicals, Ministry of Education, China (No. XJDX0908-2010 -01) and Qingdao Science and Technology Basic Research Foundation of China (No. 12-1-4-3-(6)-jch).

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Authors and Affiliations

  1. College of Chemical Engineering, Qingdao University of Science and Technology, 53 Zhengzhou Road, Qingdao, 266042, China

    Xin Jin, Kun Zhao, Fangfang Kong, Feifei Cui & Daoxing Yang

  2. Key Laboratory of Oil & Gas Fine Chemicals of Ministry of Education, Xinjiang University, Wulumuqi, 830046, China

    Xin Jin

Authors
  1. Xin Jin
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  2. Kun Zhao
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  3. Fangfang Kong
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  4. Feifei Cui
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  5. Daoxing Yang
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Correspondence to Xin Jin.

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Jin, X., Zhao, K., Kong, F. et al. Zwitterionic Phosphine Ligand with a Lysine Tag and its Application for Hydroformylation of 1-Octene in Ionic Liquid/MeOH System. Catal Lett 143, 839–843 (2013). https://doi.org/10.1007/s10562-013-0984-8

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  • DOI: https://doi.org/10.1007/s10562-013-0984-8

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