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Ionic Liquid-Based Suzuki Coupling Reaction: From Batch to Continuous Microflow System

Abstract

Transformed from heterogeneous to homogeneous state, an ionic liquid (IL)-based Suzuki coupling reaction was successfully implemented in a continuous microflow system. Triethylamine (Et3N) was introduced as the base, and N-methylpyrrolidinone (NMP) was used as the solvent of boronic acid, which brought about the first improvement on the reaction performance. Then, the implementation of this reaction in a continuous microflow system brought about further improvement on the reaction yield and selectivity due to better mixing condition. The combination of IL as the reaction medium and the continuous microflow system as the reactor in this work exhibited great potential for efficient Suzuki coupling reactions.

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References

  1. Johansson Seechurn, C. C. C.; Kitching, M. O.; Colacot, T. J.; Snieckus, V. Angew. Chem. Int. Ed. 2012, 51, 5062–5085.

    CAS  Article  Google Scholar 

  2. Suzuki, A. Angew. Chem., Int. Ed. 2011, 50, 6722–6737.

    CAS  Article  Google Scholar 

  3. Bellina, F.; Carpita, A.; Rossi, R. Synthesis 2004, 2419–2440.

    Google Scholar 

  4. Alonso, F.; Beletskaya, I. P.; Yus, M. Tetrahedron 2008, 64, 3047–3101.

    CAS  Article  Google Scholar 

  5. Kotha, S.; Lahiri, K.; Kashinath, D. Tetrahedron 2002, 58, 9633–9695.

    CAS  Article  Google Scholar 

  6. Leadbeater, N. E.; Marco, M. J. Org. Chem. 2003, 68, 888–892.

    CAS  Article  Google Scholar 

  7. Mondal, M.; Bora, U. Green Chem. 2012, 14, 1873–1876.

    CAS  Article  Google Scholar 

  8. Mathews, C. J.; Smith, P. J.; Welton, T. Chem. Commun. 2000, 1249–1250.

    Google Scholar 

  9. Leadbeater, N. E. Chem. Commun. 2014, 50, 1515–1518.

    CAS  Article  Google Scholar 

  10. McLachlan, F.; Mathews, C. J.; Smith, P. J.; Welton, T. Organometallics 2003, 22, 5350–5357.

    CAS  Article  Google Scholar 

  11. Mathews, C. J.; Smith, P. J.; Welton, T. J. Mol. Catal. A: Chem. 2004, 214, 27–32.

    CAS  Article  Google Scholar 

  12. Singh, R.; Sharma, M.; Mamgain, R.; Rawat, D. S. J. Braz. Chem. Soc. 2008, 19, 357–379.

    CAS  Article  Google Scholar 

  13. Joglekar, H. G.; Rahman, I.; Kulkarni, B. D. Chem. Eng. Technol. 2007, 30, 819–828.

    CAS  Article  Google Scholar 

  14. Hartman, R. L.; Jensen, K. F. Lab Chip 2009, 9, 2495–2507.

    CAS  Article  Google Scholar 

  15. Fukuyama, T.; Shinmen, M.; Nishitani, S.; Sato, M; Ryu, I. Org. Lett. 2002, 4, 1691–1694.

    CAS  Article  Google Scholar 

  16. Liu, S. F.; Fukuyama, T.; Sato, M.; Ryu, I. Org. Process Res. Dev. 2004, 8, 477–481.

    CAS  Article  Google Scholar 

  17. Greenway, G. M.; Haswell, S. J.; Morgan, D. O.; Skelton, V.; Styring, P. Sensors Actuat. B Chem. 2000, 63, 153–158.

    CAS  Article  Google Scholar 

  18. Basheer, C.; Jahir Hussain, F. S. J.; Lee, H. K.; Valiyaveettil, S. Tetrahedron Lett. 2004, 45, 7297–7300.

    CAS  Article  Google Scholar 

  19. Glasnov, T. N.; Kappe, C. O. Adv. Synth. Catal. 2010, 352, 3089–3097.

    CAS  Article  Google Scholar 

  20. Li, H.; Gao, X.; Ding, H.; Yang, M.; Pu, Q. Microfluid. Nanofluid. 2012, 12, 981–989.

    CAS  Article  Google Scholar 

  21. Nagaki, A.; Moriwaki, Y.; Yoshida, J. Chem. Commun. 2012, 48, 11211.

    CAS  Article  Google Scholar 

  22. Noël, T.; Kuhn, S.; Musacchio, A. J.; Jensen, K. F.; Buchwald, S. L. Angew. Chem. 2011, 50, 5943–5946.

    Article  Google Scholar 

  23. Shu, W.; Pellegatti, L.; Oberli, M. A.; Buchwald, S. L. Angew. Chem., Int. Ed. 2011, 50, 10665–10669.

    CAS  Article  Google Scholar 

  24. Shore, G.; Morin, S.; Organ, M. G. Angew. Chem. 2006, 118, 2827–2832.

    Article  Google Scholar 

  25. Amatore, C.; Jutand, A.; Le Duc, G. Chem. Eur. J. 2011, 17, 2492–2503.

    CAS  Article  Google Scholar 

  26. See http://www.organic-chemistry.org/namedreactions/suzuki-coupling.shtm.

  27. Lipshutz, B. H.; Petersen, T. B.; Abela, A. R. Org. Lett. 2008, 10, 1333–1336.

    CAS  Article  Google Scholar 

  28. Liang, Q.; Xing, P.; Huang, Z.; Dong, J.; Sharpless, K. B.; Li, X.; Jiang, B. Org. Lett. 2015, 17, 1942–1945.

    CAS  Article  Google Scholar 

  29. Wang, W.; Zhao, S.; Shao, T.; Jin, Y.; Cheng, Y. Chem. Eng. J. 2012, 192, 252–261.

    CAS  Article  Google Scholar 

  30. Gobby, D.; Angeli, P.; Gavriilidis, A. J. Micromech. Microeng. 2001, 11, 126.

    Article  Google Scholar 

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Correspondence to Yi Cheng.

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Bai, L., Fu, Y. & Cheng, Y. Ionic Liquid-Based Suzuki Coupling Reaction: From Batch to Continuous Microflow System. J Flow Chem 7, 52–56 (2017). https://doi.org/10.1556/1846.2017.00002

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  • DOI: https://doi.org/10.1556/1846.2017.00002

Keywords

  • Suzuki-Miyaura reaction
  • ionic liquid
  • microreactor
  • flow chemistry
  • homogeneous