Advertisement

Catalysis Letters

, Volume 141, Issue 6, pp 839–843 | Cite as

An Efficient and Recyclable Fluorous Palladium Catalyst for the Room-Temperature Suzuki Reaction

  • Li Wan
  • Chun Cai
Article

Abstract

A new fluorous nano-palladium catalyst was prepared and characterized. The catalytic activity of the catalyst has been evaluated for the Suzuki reaction of aryl halides and aryl boronic acids to afford the corresponding products in high yields. The reaction proceeded smoothly in the presence of 0.1 mol% catalyst in EtOH/H2O at room temperature. In addition, the catalyst could be recovered by fluorous liquid–liquid separation and reused for three times without significant loss of activity.

Graphical Abstract

The Suzuki reaction catalyzed by a new fluorous nano-palladium catalyst to afford the products in high yields at room temperature has been described. The catalyst can be recovered by fluorous liquid–liquid separation and reused for several times without significant loss of activity.

Keywords

Nano-palladium Suzuki reaction Co-solvent Fluorous palladium catalyst 

References

  1. 1.
    Hassan J, Sévignon M, Gozzi C, Schulz E, Lemaire M (2002) Chem Rev 102:1359CrossRefGoogle Scholar
  2. 2.
    Suzuki A (1999) J Organomet Chem 576:147CrossRefGoogle Scholar
  3. 3.
    Miyaura N, Suzuki A (1995) Chem Rev 95:2457CrossRefGoogle Scholar
  4. 4.
    Bellina F, Carpita A, Rossi R (2004) Synthesis 2419Google Scholar
  5. 5.
    Horton DA, Bourne GT, Smythe LM (2003) Chem Rev 103:893CrossRefGoogle Scholar
  6. 6.
    Baudoin O, Gueritte F (2003) Stud Nat Prod Chem 29:355CrossRefGoogle Scholar
  7. 7.
    Lightowler S, Hird M (2005) Chem Mater 17:5538CrossRefGoogle Scholar
  8. 8.
    Kertesz M, Choi CH, Yang S (2005) Chem Rev 105:3448CrossRefGoogle Scholar
  9. 9.
    Mei X, Wolf C (2006) J Am Chem Soc 128:13326CrossRefGoogle Scholar
  10. 10.
    Barder TE, Walker SD, Martinelli JR, Buchwald SL (2005) J Am Chem Soc 127:4685CrossRefGoogle Scholar
  11. 11.
    Herrmann WA (2002) Angew Chem Int Ed 41:1290CrossRefGoogle Scholar
  12. 12.
    Zim D, Nobre SM, Monteiro AL (2008) J Mol Catal A Chem 287:16CrossRefGoogle Scholar
  13. 13.
    Al-Hashimi M, Qazi A, Sullivan AC, Wilson JRH (2007) J Mol Catal A Chem 278:160CrossRefGoogle Scholar
  14. 14.
    Dai MJ, Liang B, Wang CH, You ZJ, Xiang J, Dong GB, Chen JH, Yang Z (2004) Adv Synth Catal 346:1669CrossRefGoogle Scholar
  15. 15.
    Yang D, Chen YC, Zhu NY (2004) Org Lett 6:1577CrossRefGoogle Scholar
  16. 16.
    Chen W, Li R, Li BJ, Chen YC, Wu Y, Ding LS, Yang D (2006) Eur J Org Chem 1177Google Scholar
  17. 17.
    Grasa GA, Singh R, Stevens ED, Nolan SP (2003) J Organomet Chem 687:269CrossRefGoogle Scholar
  18. 18.
    Buchmeiser MR, Wurst K (1999) J Am Chem Soc 121:11101CrossRefGoogle Scholar
  19. 19.
    Gossage PA, Jenkins HA, Yadav PN (2004) Tetrahedron Lett 45:7689CrossRefGoogle Scholar
  20. 20.
    Gupta AK, Song CH, Oh CH (2004) Tetrahedron Lett 45:4113CrossRefGoogle Scholar
  21. 21.
    Park SB, Alper H (2003) Org Lett 5:3209CrossRefGoogle Scholar
  22. 22.
    Deng W, Wang YF, Zou Y, Liu L, Guo QX (2004) Tetrahedron Lett 45:2311CrossRefGoogle Scholar
  23. 23.
    Liu HQ, Wang L, Ph Li (2008) Synthesis 15:2405Google Scholar
  24. 24.
    Croxtall B, Hope EG, Stuart AM (2003) Chem Commun 2003:2430CrossRefGoogle Scholar
  25. 25.
    Matsugi M, Curran DP (2005) J Org Chem 70:1636CrossRefGoogle Scholar
  26. 26.
    Molnár Á (2011) Chem Rev 111:2251CrossRefGoogle Scholar
  27. 27.
    Bernini R, Cacchi S, Fabrizi G, Forte G, Petrucci F, Prastaro A, Niembro S, Shafird A, Vallribera A (2010) Green Chem 12:150CrossRefGoogle Scholar
  28. 28.
    Bernini R, Cacchi S, Fabrizi G, Forte G, Petrucci F, Prastaro A, Niembro S, Shafird A, Vallribera A (2009) Org Biomol Chem 7:2270CrossRefGoogle Scholar
  29. 29.
    Yu MS, Curran DP, Nagashima T (2005) Org Lett 7:3677CrossRefGoogle Scholar
  30. 30.
    Chu Q, Yua MS, Curran DP (2007) Tetrahedron 63:9890CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC 2011

Authors and Affiliations

  1. 1.Chemical Engineering CollegeNanjing University of Science & TechnologyNanjingPeople’s Republic of China
  2. 2.Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic ChemistryChinese Academy of SciencesShanghaiPeople’s Republic of China

Personalised recommendations