DOI QR코드

DOI QR Code

Silica-Supported Palladium-Catalyzed Hiyama Cross-Coupling Reactions Using Continuous Flow System

  • Published : 2010.01.20

Abstract

Keywords

Continuous flow reaction;Hiyama;Palladium;Silica-supported;Immobilization

References

  1. Metal-Catalyzed Cross-Coupling Reactions, Second ed.; de Meijer, A., Diederich, F., Eds.; Wiley-VCH: 2004; Vol. 1 and 2.
  2. Farina, V.; Krishnamurthy, V.; Scott, W. J. The Stille Reaction, Wiley: New York, 1998.
  3. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483. https://doi.org/10.1021/cr00039a007
  4. Hassan, J.; Sevingnon, M.; Gozzi, D.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359-1470. https://doi.org/10.1021/cr000664r
  5. Old, D. W.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9722-9723. https://doi.org/10.1021/ja982250+
  6. Shaughnessy, K. H.; Booth, R. S. Org. Lett. 2001, 3, 2757-2759. https://doi.org/10.1021/ol0163629
  7. Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 2002, 41, 4176-4211. https://doi.org/10.1002/1521-3773(20021115)41:22<4176::AID-ANIE4176>3.0.CO;2-U
  8. Kantchev, E. A. B.; O'Brien, C. J.; Organ, M. G. Angew. Chem. Int. Ed. 2007, 46, 2768-2813. https://doi.org/10.1002/anie.200601663
  9. Fu, G. C. Acc. Chem. Res. 2008, 41, 1555-1564. https://doi.org/10.1021/ar800148f
  10. Kim, N.; Kwon, M. S.; Park, C. M.; Park, J. Tetrahedron Lett. 2004, 45, 7057-7059. https://doi.org/10.1016/j.tetlet.2004.07.126
  11. Polshettiwar, V.; Moln, A. Tetrahedron 2007, 63, 6949-6976. https://doi.org/10.1016/j.tet.2007.04.023
  12. Ooe, M.; Murata, M.; Mizugaki, T.; Ebitani, K.; Kaneda, K. J. Am. Chem. Soc. 2004, 126, 1604-1605. https://doi.org/10.1021/ja038455m
  13. Kidambi, S.; Dai, J.; Li, J.; Bruening, M. L. J. Am. Chem. Soc. 2004, 126, 2658-2659. https://doi.org/10.1021/ja038804c
  14. Kuhnert, N.; Danks, T. N. Green Chem. 2001, 3, 68-70. https://doi.org/10.1039/b008866h
  15. Fletcher, P. D. I.; Haswell, S. J.; Pombo-Villar, E.; Warrington, B. H.; Watts, P.; Wong, S. Y. F.; Zhang, X. Tetrahedron 2002, 58, 4735-4757. https://doi.org/10.1016/S0040-4020(02)00432-5
  16. Larhed, M.; Hallberg, A. J. Org. Chem. 1996, 61, 9582-9584. https://doi.org/10.1021/jo9612990
  17. Villemin, D.; Caillot, F. Tetrahedron Lett. 2001, 42, 639-642. https://doi.org/10.1016/S0040-4039(00)02027-X
  18. Kirshning, A.; Monenschein, H.; Wittenberg, R. Angew. Chem. Int. Ed. 2001, 40, 650-679. https://doi.org/10.1002/1521-3773(20010216)40:4<650::AID-ANIE6500>3.0.CO;2-C
  19. Jas, G.; Kirschning, A. Chem. Eur. J. 2003, 9, 5708-5723. https://doi.org/10.1002/chem.200305212
  20. Fletcher, P. D. I.; Haswell, S. J.; Pombo-Villar, E.; Warrington, B. H.; Watts, P.; Wong, S. Y. F.; Zhang, X. Tetrahedron 2002, 58, 4735-4757. https://doi.org/10.1016/S0040-4020(02)00432-5
  21. Hagio, H.; Sugiura, M.; Kobayashi, S. Org. Lett. 2006, 8, 375-378. https://doi.org/10.1021/ol052310y
  22. He, P.; Haswell, S. J.; Fletcher, P. D. I. Appl. Catal. A: Gen. 2004, 274, 111-114. https://doi.org/10.1016/j.apcata.2004.05.042
  23. Phan, N. T. S.; Brown, D. H.; Adams, H.; Spey, S. E.; Styring, P. Dalton Trans. 2004, 1348-1357.
  24. Karbass, N.; Sans, V.; Garcia-Verdugo, E.; Burguete, M. I.; Luis, S. V. Chem. Comm. 2006, 3095-3097.
  25. Leese, M. P.; Williams, J. M. J. Synlett 1999, 1645-1647.
  26. Hatanaka, Y.; Hiyama, T. J. Org. Chem. 1988, 53, 918-920. https://doi.org/10.1021/jo00239a056
  27. Pierrat, P.; Gros, P.; Fort, Y. Org. Lett. 2005, 7, 697-700. https://doi.org/10.1021/ol047482u
  28. Zhang, L.; Wu, J. J. Am. Chem. Soc. 2008, 130, 12250-12251. https://doi.org/10.1021/ja804672m
  29. Mowery, M. E.; DeShong, P. Org. Lett. 1999, 1, 2137-2140. https://doi.org/10.1021/ol991186d
  30. Lee, H. M.; Nolan, S. P. Org. Lett. 2000, 2, 2053-2055. https://doi.org/10.1021/ol005956t
  31. Yuranov, I.; Moeckli, P.; Suvorova, E.; Buffat, P.; Kiwi-Minsker, L.; Renken, A. J. Mol. Catal. A: Chem. 2003, 192, 239-251. https://doi.org/10.1016/S1381-1169(02)00441-7
  32. Calo, V.; Nacci, A.; Monopoli, A.; Fornaro, A.; Sabbatini, L.; Cioffi, N.; Ditaranto, N. Organometallics 2004, 23, 5154-5158. https://doi.org/10.1021/om049586e
  33. Chen, R.; Bronger, R. P. J.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Reek, J. N. H. J. Am. Chem. Soc. 2004, 126, 14557-14566. https://doi.org/10.1021/ja046956h
  34. Ju, J.; Nam, H.; Jung, H. M.; Lee, S. Tetrahedron Lett. 2006, 47, 8673-8676. https://doi.org/10.1016/j.tetlet.2006.10.017
  35. Kwon, M. S.; Kim, N.; Park, C. M.; Lee, J. S.; Kang, K. Y.; Park, J. Org. Lett. 2005, 7, 1077-1079. https://doi.org/10.1021/ol047381w
  36. Huang, J.; Jiang, T.; Gao, H.; Han, B.; Liu, Z.; Wu, W.; Chang, Y.; Zhao, G. Angew. Chem. Int. Ed. 2004, 43, 1397-1399. https://doi.org/10.1002/anie.200352682
  37. Kunz, U.; Schoenfeld, H.; Solodenko, W.; Jas, G.; Kirschnig, A. Ind. Eng. Chem. Res. 2005, 44, 8458-8467. https://doi.org/10.1021/ie048891x

Cited by

  1. Immobilized Transition Metals as Catalysts for Cross-Couplings in Continuous Flow-A Critical Assessment of the Reaction Mechanism and Metal Leaching vol.6, pp.12, 2014, https://doi.org/10.1002/cctc.201402483
  2. Ultrasonic Activation of Suzuki and Hiyama Cross-Coupling Reactions Catalyzed by Palladium vol.06, pp.02, 2016, https://doi.org/10.4236/aces.2016.62013
  3. The Hiyama Cross-Coupling Reaction: New Discoveries vol.16, pp.6, 2016, https://doi.org/10.1002/tcr.201600063
  4. Continuous flow Negishi cross-couplings employing silica-supported Pd-PEPPSI–IPr precatalyst vol.6, pp.13, 2016, https://doi.org/10.1039/C6CY00331A
  5. Palladium-Catalyzed Suzuki–Miyaura Cross-Coupling in Continuous Flow vol.7, pp.5, 2017, https://doi.org/10.3390/catal7050146
  6. ChemInform Abstract: Silica-Supported Palladium-Catalyzed Hiyama Cross-Coupling Reactions Using Continuous Flow System. vol.41, pp.22, 2010, https://doi.org/10.1002/chin.201022080