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Study on the Scale-Up of Phase-Transfer-Catalyzed Azo Coupling Reactions in Flow Reactors

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Chemistry of Heterocyclic Compounds Aims and scope

We report the first systematic study on the channel size effect in various microreactor systems on the efficiency of phase-transfercatalyzed azo coupling reactions. The optimum scaled-up channel diameter was 0.5 mm, which facilitated the synthesis of diazo compounds in high yields.

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References

  1. Wiles, C.; Watts, P. Chim. Oggi 2009, 27(3), 34.

    CAS  Google Scholar 

  2. Hessel, V.; Renken, A.; Schouten, J. C.; Yoshida, Y. Micro Process Engineering: A Comprehensive Handbook, Volume 2: Devices, Reactions and Applications; Wiley-VCH, 2009.

  3. Wiles, C.; Watts, P. Micro Reaction Technology in Organic Synthesis; CRC Press: Boca Raton, 2011.

    Google Scholar 

  4. Wiles, C.; Watts, P. Future Med. Chem. 2009, 1, 1593.

    Article  CAS  Google Scholar 

  5. Noël, T. Organmetallic Flow Chemistry; Springer, 2016.

  6. Wiles, C.; Watts, P. Chem. Commun. 2007, 443.

  7. Mason, B. P.; Price, K. E.; Steinbacher, J. L.; Bogdan, A. R.; McQuade, D. T. Chem. Rev. 2007, 107, 2300.

    Article  CAS  Google Scholar 

  8. Ahmed-Omer, B.; Brandt, J. C.; Wirth, T. Org. Biomol. Chem. 2007, 5, 733.

    Article  CAS  Google Scholar 

  9. Ley, S. V.; Fitzpatrick, D. E.; Myers, R. M.; Battilocchio, C.; Ingham, R. J. Angew. Chem., Int. Ed. 2015, 54, 10122.

  10. Baumann, M.; Baxendale, I. R. Beilstein J. Org. Chem. 2015, 11, 1194.

    CAS  Google Scholar 

  11. Nieuwland, P. J.; Segers, R.; Koch, K.; van Hest, J. C. M.; Rutjes, F. P. J. T. Org. Process Res. Dev. 2011, 15, 783.

    Article  CAS  Google Scholar 

  12. Bagley, M. C.; Fusillo,V.; Jenkins, L. R.; Lubinu, M. C.; Mason, C. Beilstein J. Org. Chem. 2013, 9, 1957.

  13. Wahab, B.; Ellames, G.; Passey, S.; Watts, P. Tetrahedron 2010, 66, 3861.

    Article  CAS  Google Scholar 

  14. Fuchs, M.; Goessler, W.; Pilger, C.; Kappe, C. O. Adv. Synth. Catal. 2010, 352, 323.

    Article  CAS  Google Scholar 

  15. Bogdan, A. R.; James, K. Org. Lett. 2011, 13, 4060.

    Article  CAS  Google Scholar 

  16. Suga, S.; Okajima, M.; Fujiwara, K.; Yoshida, J. J. Am. Chem. Soc. 2001, 123, 7941.

    Article  CAS  Google Scholar 

  17. Nagaki, A.; Togai, M.; Suga, S.; Aoki, N.; Mae, K.; Yoshida, J. J. Am. Chem. Soc. 2005, 127, 11666.

    Article  CAS  Google Scholar 

  18. Venturoni, F.; Nikbin, N.; Ley, S. V.; Baxendale, I. R. Org. Biomol. Chem. 2010, 8, 1798.

    Article  CAS  Google Scholar 

  19. Akwi, F. M.; Bosma, C.; Watts, P. J. Flow Chem. 2016, 6, 73.

    Article  Google Scholar 

  20. Zhao, C.-X.; Middelberg, A. P. J. Chem. Eng. Sci. 2011, 66, 1394.

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The authors would like to acknowledge Nelson Mandela Metropolitan University and the National Research Foundation of South Africa for financial support.

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Correspondence to Paul Watts.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2016, 52(11), 943–947

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Akwi, F.M., Watts, P. Study on the Scale-Up of Phase-Transfer-Catalyzed Azo Coupling Reactions in Flow Reactors. Chem Heterocycl Comp 52, 943–947 (2016). https://doi.org/10.1007/s10593-017-1990-3

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  • DOI: https://doi.org/10.1007/s10593-017-1990-3

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