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
- 2.
Williams DBG, Shaw ML, Hughes T (2011) Organometallics 30:4968
- 3.
Tortosa-Estorach C, Ruiz N, Masdeu-Bulto AM (2006) Chem Commun 26:2789
- 4.
del Río I, Claver C, van Leeuwen PWNM (2001) Eur J Inorg Chem 2001:2719
- 5.
Seayad A, Kelkar AA, Chaudhari RV, Toniolo L (1998) Ind Eng Chem Res 37:2180
- 6.
Zhou LM, Guo CH, Fu HY, Jiang XH, Chen H, Li RX, Li XJ (2012) Spectrochimica Acta Part A 93:198
- 7.
Jayasree S, Seayad A, Chaudhari RV (2000) Chem Commun 2000:1239
- 8.
Tilloy S, Monflier E, Bertoux F, Castanet Y, Mortreux A (1997) New J Chem 21:529
- 9.
Bertoux F, Tilloy S, Monflier E, Castanet Y, Mortreux A (1999) J Mol Catal A: Chem 138:53
- 10.
Bertoux F, Monflier E, Castanet Y, Mortreux A (1999) J Mol Catal A: Chem 143:11
- 11.
Karlsson M, Ionescu A, Andersson C (2006) J Mol Catal A: Chem 259:231
- 12.
Six N, Guerriero A, Landy D, Peruzzini M, Gonsalvi L, Hapiot F, Monflier E (2011) Catal Sci Technol 1:1347
- 13.
Franke R, Selent D, Börner A (2012) Chem Rev 112:58
- 14.
Aghmiz A, Giménez-Pedrós M, Masdeu-Bultó A, Schmidtchen FP (2005) Catal Lett 103:191
- 15.
Duvenhage DJ, Coville NJ (2005) Catal Lett 104:129
- 16.
Monflier E, Tilloy S, Bertoux F, Castanet Y, Mortreux A (1997) New J Chem 21:857
- 17.
Tilloy S, Bertoux F, Mortreux A, Monflier E (1999) Catal Today 48:245
- 18.
Li Z, Peng Q, Yuan Y (2003) Appl Catal A Gen 239:79
- 19.
Bertoux F, Monflier E, Castanet Y, Mortreux A (1999) J Mol Catal A: Chem 143:23
- 20.
Mukhopadhyay K, Sarkar BR, Chaudhari RV (2002) J Am Chem Soc 124:9692
- 21.
Seayad A, Jayasree S, Damodaran K, Toniolo L, Chaudhari RV (2000) J Organomet Chem 601:100
- 22.
Seayad A, Kelkar AA, Toniolo L, Chaudhari RV (2000) J Mol Catal A: Chem 151:47
- 23.
Atla SB, Kelkar AA, Chaudhari RV (2009) J Mol Catal A: Chem 307:134
- 24.
Seayad A, Jayasree S, Chaudhari RV (1999) Org Lett 1:459
- 25.
Ding H, Hanson BE (1994) J Chem Soc, Chem Commun 13:2747
- 26.
Ionescu A, Ruppel M, Wendt OF (2006) J Organomet Chem 691:3806
- 27.
Papadogianakis G, Peters JA, Maat L, Sheldon RA (1995) J Chem Soc, Chem Commun 32:1105
- 28.
Papadogianakis G, Verspui G, Maat L, Sheldon RA (1997) Catal Lett 47:43
- 29.
Binkowski C, Cabou J, Bricout H, Hapiot F, Monflier E (2004) J Mol Catal A: Chem 215:23
- 30.
Ali BE, Fettouhi M (2002) J Mol Catal A: Chem 182–183:195
- 31.
Fontana G, Lubineau A, Scherrmann MC (2005) Org Biomol Chem 3:1375
- 32.
Benedek C, Törös S, Heil B (1999) J Organomet Chem 586:85
- 33.
Klingshirn MA, Rogers RD, Shaughnessy KH (2005) J Organomet Chem 690:3620
- 34.
Kuntz EG, Vittori OM (1998) J Mol Catal A: Chem 129:159
- 35.
del Río I, Ruiz N, Claver C, van der Veen LA, van Leeuwen PWNM (2000) J Mol Catal A Chem 161: 39
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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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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Keywords
- Aqueous two-phase system
- Hydrocarboxylation
- Palladium-phosphine complexes
- Alkali metal halide