Catalysis Letters

, 129:363 | Cite as

Suzuki Cross-Coupling Reaction Catalyzed by the Palladium Complex Pd[N-MorphC(S)NP(O)(OiPr)2-O,S]2

  • Damir A. Safin
  • Maria G. Babashkina
  • Axel Klein


Suzuki cross-coupling reaction between phenyl bromide and phenylboronic acid, catalyzed by the palladium complex Pd[N-MorphC(S)NP(O)(OiPr)2-1,5-O,S)]2 in acetonitrile, toluene, THF or DMF has been investigated. Bases employed for the reaction were Na2CO3, K2CO3 or Cs2CO3. Varying largely the experimental conditions we found that excellent yields of the product were obtained using toluene and K2CO3 at 100 °C at the catalyst amount of 0.02 mmol.


Cross-coupling Phenylboronic acid Phenyl bromide Suzuki-Miyaura reaction N-Phosphorylthiourea Palladium 



This work was supported by the joint program of CRDF and the Russian Ministry of Education and Science (BRHE 2008 Y5-C-07-09); Russian Science Support Foundation. DAS and MGB thank DAAD for the scholarships (Forschungsstipendien 2008/2009).


  1. 1.
    Martin R, Buchwald SL Acc Chem Res. doi:  10.1021/ar800036s
  2. 2.
    Weng Z, Teo S, Hor TSA (2007) Acc Chem Res 40:676CrossRefGoogle Scholar
  3. 3.
    Phan NTS, Sluys MVD, Jones CV (2006) Adv Synth Catal 348:609CrossRefGoogle Scholar
  4. 4.
    Miyaura N (2004) In: Diederich F, de Meijere A (eds) Metal-catalyzed cross-coupling reaction, Wiley-VCH, New York, Chap 2Google Scholar
  5. 5.
    Bellina F, Carpita A, Rossi R (2004) Synthesis 15:2419Google Scholar
  6. 6.
    Kotha S, Lahiri K, Kashinath D (2002) Tetrahedron 58:9633CrossRefGoogle Scholar
  7. 7.
    Suzuki A (2002) J Organomet Chem 653:83CrossRefGoogle Scholar
  8. 8.
    Hassan J, Sevignon M, Gozzi C, Schulz E, Lemaire M (2002) Chem Rev 102:1359CrossRefGoogle Scholar
  9. 9.
    Littke AF, Fu GC (2002) Angew Chem Int Ed 41:4176CrossRefGoogle Scholar
  10. 10.
    Chemler SR, Trauner D, Danishefsky SJ (2001) Angew Chem Int Ed 40:4544CrossRefGoogle Scholar
  11. 11.
    Suzuki A (1999) J Organomet Chem 576:147CrossRefGoogle Scholar
  12. 12.
    Miyaura N, Suzuki A (1995) Chem Rev 95:2457CrossRefGoogle Scholar
  13. 13.
    Kantchev EAB, O’Brien CJ, Organ MG (2007) Angew Chem Int Ed 46:2768 refernces thereinCrossRefGoogle Scholar
  14. 14.
    Liu W-J, Xie Y-X, Liang Y, Li J-H (2006) Synthesis 8:860CrossRefGoogle Scholar
  15. 15.
    Dai M, Liang B, Wang C, Chen J, Yang Z (2004) Org Lett 6:1577CrossRefGoogle Scholar
  16. 16.
    Dai M, Liang B, Wang C, Chen J, Yang Z (2004) Org Lett 6:221CrossRefGoogle Scholar
  17. 17.
    Sokolov FD, Baranov SV, Safin DA, Hahn FE, Kubiak M, Pape T, Babashkina MG, Zabirov NG, Galezowska J, Kozlowski H, Cherkasov RA (2007) New J Chem 31:1661CrossRefGoogle Scholar
  18. 18.
    Safin DA, Sokolov FD, Szyrwiel Ł, Baranov SV, Babashkina MG, Gimadiev TR, Kozlowski H (2008) Polyhedron 27:1995CrossRefGoogle Scholar
  19. 19.
    Safin DA, Szyrwiel Ł, Baranov SV, Sokolov FD, Babashkina MG, Kozlowski H (2008) Inorg Chem Commun 11:330CrossRefGoogle Scholar
  20. 20.
    Sokolov FD, Zabirov NG, Yamalieva LN, Shtyrlin VG, Garipov RR, Brusko VV, Verat AYu, Baranov SV, Mlynarz P, Glowiak T, Kozlowski H (2006) Inorg Chim Acta 359:2087CrossRefGoogle Scholar
  21. 21.
    Safin DA, Babashkina MG (2008) Inorg Chim Acta (submitted)Google Scholar
  22. 22.
    Safin DA, Sokolov FD, Baranov SV, Hahn FE, Pape T,Babashkina MG (2008) Polyhedron (submitted)Google Scholar
  23. 23.
    Zabirov NG (1995) Synthesis, structure and properties of N-acyl- and Nacyl(thio)amidophosphates, Doctor thesis, Kazan State University, Kazan, Russia, p. 483Google Scholar
  24. 24.
    Solov’ev VN, Shamsevaleev FM, Cherkasov RA, Chekhlov AN, Tsifarkin AG, Martynov IV (1991) Russ J Gen Chem (USSR) 61:657Google Scholar

Copyright information

© Springer Science+Business Media, LLC 2008

Authors and Affiliations

  • Damir A. Safin
    • 1
    • 2
  • Maria G. Babashkina
    • 1
    • 2
  • Axel Klein
    • 2
  1. 1.A. M. Butlerov Chemistry InstituteKazan State UniversityKazanRussian Federation
  2. 2.Institut für Anorganische ChemieUniversität zu KölnCologneGermany

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