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Effects of Alkali Halide Salts on Hydrocarboxylation of Styrene Catalyzed by Water-Soluble Palladium Phosphine Complexes

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Abstract

Hydrocarboxylation of styrene catalyzed by water-soluble Pd-TPPTS complexes was investigated. The reaction conditions, including reaction pressure, temperature, time and etc. have a significant influence on the catalytic performance. It was found that the yield of total acids and the selectivity towards 3-phenylpropionic acid were enhanced by adding a suitable amount of alkali metal halide salts. In addition, the reaction mechanism and the role of alkali metal halide salts in the reaction were discussed on the basis of the characterization of 1H NMR and 31P NMR.

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References

  1. Lapidus A, Eliseev O, Bondarenko T, Stepin N (2006) J Mol Catal A: Chem 252:245

    Article  CAS  Google Scholar 

  2. Williams DBG, Shaw ML, Hughes T (2011) Organometallics 30:4968

    Article  CAS  Google Scholar 

  3. Tortosa-Estorach C, Ruiz N, Masdeu-Bulto AM (2006) Chem Commun 26:2789

    Article  Google Scholar 

  4. del Río I, Claver C, van Leeuwen PWNM (2001) Eur J Inorg Chem 2001:2719

    Google Scholar 

  5. Seayad A, Kelkar AA, Chaudhari RV, Toniolo L (1998) Ind Eng Chem Res 37:2180

    Article  CAS  Google Scholar 

  6. Zhou LM, Guo CH, Fu HY, Jiang XH, Chen H, Li RX, Li XJ (2012) Spectrochimica Acta Part A 93:198

    Article  CAS  Google Scholar 

  7. Jayasree S, Seayad A, Chaudhari RV (2000) Chem Commun 2000:1239

    Article  Google Scholar 

  8. Tilloy S, Monflier E, Bertoux F, Castanet Y, Mortreux A (1997) New J Chem 21:529

    CAS  Google Scholar 

  9. Bertoux F, Tilloy S, Monflier E, Castanet Y, Mortreux A (1999) J Mol Catal A: Chem 138:53

    Article  CAS  Google Scholar 

  10. Bertoux F, Monflier E, Castanet Y, Mortreux A (1999) J Mol Catal A: Chem 143:11

    Article  CAS  Google Scholar 

  11. Karlsson M, Ionescu A, Andersson C (2006) J Mol Catal A: Chem 259:231

    Article  CAS  Google Scholar 

  12. Six N, Guerriero A, Landy D, Peruzzini M, Gonsalvi L, Hapiot F, Monflier E (2011) Catal Sci Technol 1:1347

    Article  CAS  Google Scholar 

  13. Franke R, Selent D, Börner A (2012) Chem Rev 112:58

    Article  Google Scholar 

  14. Aghmiz A, Giménez-Pedrós M, Masdeu-Bultó A, Schmidtchen FP (2005) Catal Lett 103:191

    Article  CAS  Google Scholar 

  15. Duvenhage DJ, Coville NJ (2005) Catal Lett 104:129

    Article  CAS  Google Scholar 

  16. Monflier E, Tilloy S, Bertoux F, Castanet Y, Mortreux A (1997) New J Chem 21:857

    CAS  Google Scholar 

  17. Tilloy S, Bertoux F, Mortreux A, Monflier E (1999) Catal Today 48:245

    Article  CAS  Google Scholar 

  18. Li Z, Peng Q, Yuan Y (2003) Appl Catal A Gen 239:79

    Article  CAS  Google Scholar 

  19. Bertoux F, Monflier E, Castanet Y, Mortreux A (1999) J Mol Catal A: Chem 143:23

    Article  CAS  Google Scholar 

  20. Mukhopadhyay K, Sarkar BR, Chaudhari RV (2002) J Am Chem Soc 124:9692

    Article  CAS  Google Scholar 

  21. Seayad A, Jayasree S, Damodaran K, Toniolo L, Chaudhari RV (2000) J Organomet Chem 601:100

    Article  CAS  Google Scholar 

  22. Seayad A, Kelkar AA, Toniolo L, Chaudhari RV (2000) J Mol Catal A: Chem 151:47

    Article  CAS  Google Scholar 

  23. Atla SB, Kelkar AA, Chaudhari RV (2009) J Mol Catal A: Chem 307:134

    Article  CAS  Google Scholar 

  24. Seayad A, Jayasree S, Chaudhari RV (1999) Org Lett 1:459

    Article  CAS  Google Scholar 

  25. Ding H, Hanson BE (1994) J Chem Soc, Chem Commun 13:2747

    Article  Google Scholar 

  26. Ionescu A, Ruppel M, Wendt OF (2006) J Organomet Chem 691:3806

    Article  CAS  Google Scholar 

  27. Papadogianakis G, Peters JA, Maat L, Sheldon RA (1995) J Chem Soc, Chem Commun 32:1105

    Article  Google Scholar 

  28. Papadogianakis G, Verspui G, Maat L, Sheldon RA (1997) Catal Lett 47:43

    Article  CAS  Google Scholar 

  29. Binkowski C, Cabou J, Bricout H, Hapiot F, Monflier E (2004) J Mol Catal A: Chem 215:23

    Article  CAS  Google Scholar 

  30. Ali BE, Fettouhi M (2002) J Mol Catal A: Chem 182–183:195

    Article  Google Scholar 

  31. Fontana G, Lubineau A, Scherrmann MC (2005) Org Biomol Chem 3:1375

    Article  CAS  Google Scholar 

  32. Benedek C, Törös S, Heil B (1999) J Organomet Chem 586:85

    Article  CAS  Google Scholar 

  33. Klingshirn MA, Rogers RD, Shaughnessy KH (2005) J Organomet Chem 690:3620

    Article  CAS  Google Scholar 

  34. Kuntz EG, Vittori OM (1998) J Mol Catal A: Chem 129:159

    Article  CAS  Google Scholar 

  35. del Río I, Ruiz N, Claver C, van der Veen LA, van Leeuwen PWNM (2000) J Mol Catal A Chem 161: 39

    Google Scholar 

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Acknowledgments

The authors are grateful for the support from the National Natural Science Foundation of China (U1179302) and One Hundred Person Project of the Chinese Academy of Sciences.

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Correspondence to Zhenshan Hou.

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He, Z., Hou, Z., Luo, Y. et al. Effects of Alkali Halide Salts on Hydrocarboxylation of Styrene Catalyzed by Water-Soluble Palladium Phosphine Complexes. Catal Lett 143, 289–297 (2013). https://doi.org/10.1007/s10562-013-0961-2

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