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Chiral metal-containing ionic liquid: Synthesis and applications in the enantioselective cycloaddition of carbon dioxide to epoxides

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Abstract

A series of novel chiral metal-containing ionic liquids (CMILs) consisting of the cation of crown ether-chelated potassium/sodium and the anion of chiral amino acids were designed and synthesized. These new CMILs were used to catalyze the enantioselective cycloaddition of epoxides and carbon dioxide incorporating with the salenCo(OOCCCl3) to generate corresponding chiral cyclic carbonates under mild conditions. These new catalysts can be recycled at least five times without significant loss of activity and enantioselectivity.

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References

  1. Sheldon R. Catalytic reactions in ionic liquids. Chem Commun, 2001, 23: 2399–2407

    Article  Google Scholar 

  2. Dupont J, de Souza RF, Suarez PAZ. Ionic liquid (molten salt) phase organometallic catalysis. Chem Rev, 2002, 102: 3667–3692

    Article  CAS  Google Scholar 

  3. Binnemans K. Ionic liquid crystals. Chem Rev, 2005, 105: 4148–4204

    Article  CAS  Google Scholar 

  4. van Rantwijk F, Sheldon RA. Biocatalysis in ionic liquids. Chem Rev, 2007, 107: 2757–2785

    Article  Google Scholar 

  5. Mehnert CP. Supported ionic liquid catalysis. Chem Eur J, 2005, 11: 50–56

    Article  Google Scholar 

  6. Tao GH, He L, Liu WS, Xu L, Xiong W, Wang T, Kou Y. Preparation, characterization and application of amino acid-based green ionic liquids. Green Chem, 2006, 8: 639–646

    Article  CAS  Google Scholar 

  7. Feder-Kubis J, Kubicki M, Pernak J. 3-Alkoxymethyl-1-(1R,2S, 5R)-(−)-menthoxymethylimidazolium salts-based chiral ionic liquids. Tetrahedron Asymmetry, 2010, 21: 2709–2718

    Article  CAS  Google Scholar 

  8. Winkel A, Wilhelm R. New chiral ionic liquids based on imidazolinium salts. Tetrahedron Asymm, 2009, 20: 2344–2350

    Article  CAS  Google Scholar 

  9. Mloston G, Romanski J, Jasinski M, Heimgartner H. Exploration of 4,5-dimethyl-1H-imidazole N-oxide derivatives in the synthesis of new achiral and chiral ionic liquids. Tetrahedron Asymm, 2009, 20: 1073–1080

    Article  CAS  Google Scholar 

  10. Rahman MBA, Jumbri K, Basri M, Abdulmalek E, Sirat K, Salleh AB. Synthesis and physico-chemical properties of new tetraethylammonium-based amino acid chiral ionic liquids. Molecules, 2010, 15: 2388–2397

    Article  Google Scholar 

  11. Welton T. Room-temperature ionic liquids. solvents for synthesis and catalysis. Chem Rev, 1999, 99: 2071–2084

    Article  CAS  Google Scholar 

  12. Wasserscheid P, Keim W. Ionic liquids-new “solutions” for transition metal catalysis. Angew Chem Int Ed, 2000, 39: 3772–3789

    CAS  Google Scholar 

  13. Yang HZ, Gu YL, Deng YQ and Shi F. Electrochemical activation of carbon dioxide in ionic liquid: Synthesis of cyclic carbonates at mild reaction conditions. Chem Commun, 2002, 274–275

  14. Pârvulescu VI, Hardacre C. Catalysis in ionic liquids. Chem Rev, 2007, 107: 2615–1665

    Article  Google Scholar 

  15. Olivier-Bourbigou H, Magna L, Morvan D. Ionic liquids and catalysis: Recent progress from knowledge to applications. Appl Catal A: Gen, 2010, 373: 1–56

    Article  CAS  Google Scholar 

  16. Maltsev OV, Kucherenko AS, Chimishkyan AL, Zlotin SG. α,α-Diarylprolinol-derived chiral ionic liquids: recoverable organocatalysts for the domino reaction between α,β-enals and N-protected hydroxylamines. Tetrahedron Asymm, 2010, 21: 2659–2670

    Article  CAS  Google Scholar 

  17. Xie Y, Zhang ZF, Jiang T, He JL, Han BX, Wu TB, Ding KL. CO2 Cycloaddition reactions catalyzed by an ionic liquid grafted onto a highly cross-linked polymer matrix. Angew Chem Int Ed, 2007, 46: 7255–7258

    Article  CAS  Google Scholar 

  18. Kim YJ, Varma RS. Tetrahaloindate(III)-based ionic liquids in the coupling reaction of carbon dioxide and epoxides to generate cyclic carbonates: H-bonding and mechanistic studies. J Org Chem, 2005, 70: 7882–7891

    Article  CAS  Google Scholar 

  19. Li FW, Xiao LF, Xia CG, Hu B. Chemical fixation of CO2 with highly efficient ZnCl2/[BMIm]Br catalyst system. Tetrahedron Lett, 2004, 45: 8307–8310

    Article  CAS  Google Scholar 

  20. Wong WL, Chan PH, Zhou ZY, Lee KH, Cheung KC, Wong KY. A robust ionic liquid as reaction medium and efficient organocatalyst for carbon dioxide fixation. ChemSusChem, 2008, 1: 67–70

    Article  CAS  Google Scholar 

  21. Yang ZZ, He LN, Miao CX, Chanfreau S. Lewis basic ionic liquids-catalyzed conversion of carbon dioxide to cyclic carbonate. Adv Synth Catal, 2010, 352: 2233–2240

    Article  CAS  Google Scholar 

  22. Zhang SL, Huang YZ, Jing HW, Yao WX, Yan P. Chiral ionic liquids improved the asymmetric cycloaddition of CO2 to epoxides. Green Chem, 2009, 11: 935–938

    Article  Google Scholar 

  23. Lu XB, Liang B, Zhang YJ, Tian ZY, Wang YM, Bai CX, Wang H, Zhang R. Asymmetric catalysis with CO2: Direct synthesis of optically active propylene carbonate from racemic epoxides. J Am Chem Soc, 2004, 126: 3732–3733

    Article  CAS  Google Scholar 

  24. Yan P and Jing HW. Catalytic asymmetric cycloaddition of carbon dioxide and propylene oxide using novel chiral polymers of binolsalen-cobalt(III) salts. Adv Synth Catal, 2009, 351: 1325–1332

    Article  CAS  Google Scholar 

  25. Jin LL, Huang YZ, Jing HW, Chang T, Yan P. Chiral catalysts for the asymmetric cycloaddition of carbon dioxide with epoxides. Tetrahedron: Asymm, 2008, 19: 1947–1953

    Article  CAS  Google Scholar 

  26. Chang T, Jin LL, Jing HW. Bifunctional chiral catalyst for the synthesis of chiral cyclic carbonates from carbon dioxide and epoxides. ChemCatChem, 2009, 1: 379–383

    Article  CAS  Google Scholar 

  27. Berkessel A and Brandenburg M. Catalytic asymmetric addition of carbon dioxide to propylene oxide with unprecedented enantioselectivity. Org Lett, 2006, 8: 4401–4404

    Article  CAS  Google Scholar 

  28. Chen SW, Kawthekar RB, Kim GJ. Efficient catalytic synthesis of optically active cyclic carbonates via coupling reaction of epoxides and carbon dioxide. Tetrahedron Lett, 2007, 48: 297–300

    Article  CAS  Google Scholar 

  29. Yamada W, Kitaichi Y, Tanaka H, Kojima T, Sato M, Ikeno T, Yamada T. Enantioselective incorporation of carbon dioxide into epoxides catalyzed by optically active cobalt(II) complexes. Bull Chem Soc Jpn, 2007, 80: 1391–1401

    Article  CAS  Google Scholar 

  30. Sakakura T and Kohno K. The synthesis of organic carbonates from carbon dioxide. Chem Commun, 2009, 1312-1310

  31. North M, Pasquale R, Young C. Synthesis of cyclic carbonates from epoxides and CO2. Green Chem, 2010, 12: 1514–1539

    Article  CAS  Google Scholar 

  32. Chang T, Jing HW, Jin LL, Qiu WY. Quaternary onium tribromide catalyzed cyclic carbonate synthesis from carbon dioxide and epoxides. J Mol Catal A: Chem, 2007, 264: 241–247

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. State Key Laboratory of Applied Organic Chemistry; College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, 730000, China

    YingYing Song, QianRu Jin, SuLing Zhang, HuanWang Jing & QianQian Zhu

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  1. YingYing Song
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  2. QianRu Jin
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  3. SuLing Zhang
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  4. HuanWang Jing
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  5. QianQian Zhu
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Correspondence to HuanWang Jing.

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Song, Y., Jin, Q., Zhang, S. et al. Chiral metal-containing ionic liquid: Synthesis and applications in the enantioselective cycloaddition of carbon dioxide to epoxides. Sci. China Chem. 54, 1044–1050 (2011). https://doi.org/10.1007/s11426-011-4274-2

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  • DOI: https://doi.org/10.1007/s11426-011-4274-2

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