Advertisement

Catalysis Letters

, Volume 145, Issue 7, pp 1396–1402 | Cite as

Methoxycarbonylation of Styrene Using a New Type of Palladium Complexes Bearing P,N-donor Ligands as Catalysts

  • Gabriel Abarca
  • Kareen Brown
  • Sergio A. Moya
  • J. Carles Bayón
  • Pedro A. Aguirre
Article
  • 328 Downloads

Abstract

Palladium complexes of the type [Pd(L)Cl(PPh3)]Cl (L = 2-diphenylphosphinoamino)pyrimidine, or 2-diphenylphosphinoaniline), generated in situ by addition of one equivalent of PPh3 to the corresponding neutral complexes [Pd(L)Cl2], were tested as catalysts for the methoxycarbonylation of styrene. The catalyst containing the pyrimidinyl ligand shows almost complete chemo- and regioselectivity together with a high conversion rate. However, in identical conditions, the [Pd(Ph2PNHC6H4PPh2)Cl2] complex, where the P,N-ligand has been replaced by a related bidentate P-donor one, shows a significantly lesser performance.

Graphical Abstract

Keywords

Palladium catalyst Phosphorus nitrogen ligand Methoxycarbonylation Styrene Homogeneous catalysis 

Notes

Acknowledgments

We are grateful for the financial support provided by Fondecyt-Chile (Grant 1120149) and to Daniel Peral (UAB) for his valuable comments.

References

  1. 1.
    Bell S, Wuestenberg B, Kaiser S, Menges F, Netscher T, Pfaltz A (2006) Science 311:642–644CrossRefGoogle Scholar
  2. 2.
    Pàmies O, Andersson PG, Diéguez M (2010) Chem Eur J 16:14232–14240CrossRefGoogle Scholar
  3. 3.
    Kumar P, Kumar Singh A, Yadav M, Li P, Singh SK, Xu Q, Pandey DS (2011) Inorg Chim Acta 368:124–131CrossRefGoogle Scholar
  4. 4.
    Bichler B, Veiros LF, Öztopcu Ö, Puchberger M, Mereiter K, Matsubara K, Kirchner KA (2011) Organometallics 30:5928–5942CrossRefGoogle Scholar
  5. 5.
    Schareina T, Kempe R (2002) Angew Chem Int Ed 41:1521–1523CrossRefGoogle Scholar
  6. 6.
    Proch S, Kempe R (2007) Angew Chem Int Ed 46:3135–3138CrossRefGoogle Scholar
  7. 7.
    Michlik S, Kempe R (2010) Chem Eur J 16:13193–13198CrossRefGoogle Scholar
  8. 8.
    Leca F, Fernández F, Muller G, Lescop C, Réau R, Gómez M (2009) Eur J Inorg Chem 36:5583–5591CrossRefGoogle Scholar
  9. 9.
    Mata Y, Pàmies O, Diéguez M (2009) Adv Synt Catal 351:3217–3234CrossRefGoogle Scholar
  10. 10.
    Wehman P, van Donge HMA, Hagos A, Kamer PCJ, van Leeuwen PWNM (1997) J Organomet Chem 535:183–193CrossRefGoogle Scholar
  11. 11.
    Burrows AD, Mahon MF, Varrone M (2003) Dalton Trans 4718–4730Google Scholar
  12. 12.
    Dekker GPCM, Buijs A, Elsevier CJ, Vrieze K, van Leeuwen PWNM, Smeets WJJ, Spek AL, Wang YF, Stam CH (1992) Organometallics 11:1937–1948CrossRefGoogle Scholar
  13. 13.
    Crawford L, Cole-Hamilton DJ, Drent E, Buehl M (2014) Chem Eur J 20:13924–13926 and references thereinCrossRefGoogle Scholar
  14. 14.
    Zhang X, Zhao W, Zhang S (1995) Shiyou Huagong 24:691–694Google Scholar
  15. 15.
    Beller M, Tafesh AM (2002) In: Cornils B, Hermann WA (eds) Applied homogeneous catalysis with organometallics compounds catalysis with organometallics compounds, 2nd edn. Wiley, Weinheim, pp 182–194Google Scholar
  16. 16.
    van Leeuwen PWNM (2004) Homogenous catalysis. Kluwer Academic Publishers, Dordrecht, pp 239–270CrossRefGoogle Scholar
  17. 17.
    Brennführer A, Neumann H, Beller M (2009) ChemCatChem 1:28–41CrossRefGoogle Scholar
  18. 18.
    Godard C, Ruiz A, Diéguez M, Pàmies O, Claver C (2010) In: Ojima I (ed) Catalytic asymmetric synthesis, 3rd edn. Wiley, Hoboken, pp 799–838CrossRefGoogle Scholar
  19. 19.
    Eastham GR, Tooze RP, Wang XL, Whiston K (1996) WO1996019434 PatentGoogle Scholar
  20. 20.
    Kiss G (2001) Chem Rev 101:3435–3456CrossRefGoogle Scholar
  21. 21.
    Blanco C, Godard C, Zangrando E, Ruiz A, Claver C (2011) Dalton Trans 41:6980–6991 and references thereinCrossRefGoogle Scholar
  22. 22.
    Jedlicka B, Weissensteiner W, Kégl T, Kollár L (1998) J Organomet Chem 563:37–41CrossRefGoogle Scholar
  23. 23.
    Aguirre PA, Lagos C, Moya SA, Zúñiga C, Vera-Oyarce C, Sola E, Peris G, Bayón JC (2007) Dalton Trans 46:5419–5426CrossRefGoogle Scholar
  24. 24.
    Scheurmann ML, Grice KA, Ruppel MJ, Roselló-Merino M, Kamisnsky W, Goldberg KI (2014) Organometallics 43:12018–12025Google Scholar
  25. 25.
    Cooper MK, Downes JM, Duckworth PA (1989) Inorg Synth 25:129–133CrossRefGoogle Scholar
  26. 26.
    Floerke U, Haupt HJ (1993) Z Kristallogr 205:127–128CrossRefGoogle Scholar
  27. 27.
    Aucott SM, Slawin AMZ, Woollins JD (1999) J Organomet Chem 582:83–89CrossRefGoogle Scholar
  28. 28.
    Chatterjee S, Hockless DCR, Salem G, Waring P (1997) J Chem Soc Dalton Trans 3889–3895Google Scholar
  29. 29.
    Aucott SM, Slawin AMZ, Woolins JD (2001) Dalton Trans 2279–2287Google Scholar

Copyright information

© Springer Science+Business Media New York 2015

Authors and Affiliations

  • Gabriel Abarca
    • 1
  • Kareen Brown
    • 2
  • Sergio A. Moya
    • 2
  • J. Carles Bayón
    • 3
  • Pedro A. Aguirre
    • 1
  1. 1.Facultad de Ciencias Químicas y FarmacéuticasUniversidad de ChileSantiago 1Chile
  2. 2.Facultad de Química y BiologíaUniversidad de Santiago de ChileSantiagoChile
  3. 3.Departament de QuímicaUniversitat Autonòma de BarcelonaBarcelonaSpain

Personalised recommendations