The effect of ultrasound on the yields of Heck reaction using Pd-catalyst in DMF/water

Authors

  • Said Khemais Physical Organic Chemistry Laboratory, University of Sfax, Faculty of Science, 3018, Sfax, Tunisia.
  • Majed Kammoun Chemistry laboratory Of the Natural Substances, University of Sfax, Faculty of Science, 3018, Sfax, Tunisia.
  • Younes Moussaoui Physical Organic Chemistry Laboratory, University of Sfax, Faculty of Science, 3018, Sfax, Tunisia.
  • Ridha Ben Salem Physical Organic Chemistry Laboratory, University of Sfax, Faculty of Science, 3018, Sfax, Tunisia.

DOI:

https://doi.org/10.13171/mjc.1.1.2011.18.05.12

Abstract

The heck reaction of aryl bromide with styrene in N,N-dimethyl formamide/water as solvent has been studied using different catalysts under ultrasonic irradiation at room temperature. The effect of the solvent, the base, and the catalyst of the transfer phase were studied. The results show that ultrasonic irradiation increases the heck reaction yield and becomes faster with the amount of aliquat-336.

References

- A. de Meijere, F.E. Meyer, Angew. Chem. Int. Ed., 1995, 33, 2379-2411.

- S. H. Huang, J. R. Chen, F. Y. Tsai, Molecules, 2010, 15, 315-330.

- K. Said, Y. Moussaoui, R. Ben Salem, J. Soc. Chim. Tunisie, 2009, 11, 59-67.

- I. P. Beleskaya, A. V. Cheprakov, Chem. Rev., 2000, 100, 3009-3066.

- A. B. Dounay, L.E. Overman, Chem. Rev., 2003, 103, 2945-2964.

- D. Astruc, Inorg. Chem., 2007, 46, 1884-1894.

- S. Lee, J. Organomet. Chem., 2006, 691, 1347-1355.

- G. V. Ambulgekar, B. M. Bhanage, S. D. Samant, Tetrahedron Lett., 2005, 46, 2483-2485.

- R. F. Heck, Acc. Chem. Res., 1979, 12, 146-151.

- U. Christmann, R. Vilar, Angew. Chem. Int. Ed., 2005, 44, 366-374.

- A. Corma, H. Garcia, A. Leyva, A. Primo, Appl. Catal. A, 2004, 257, 77-83.

- C. Yi, R. Hua, Tetrahedron Lett., 2006, 47, 2573-2576. 13 - S. Mohanty, D. Suresh, M. S. Balakrishna, J. T. Mague, Tetrahedron, 2008, 64, 240-247.

- Y. Cai, Y. Lu, Y. Liu, M. He, Q. Wan, Catalysis Commun., 2008, 9, 1209-1213.

- H. J. Li, L. Wang, Eur. J. Org. Chem., 2006, 71, 5099-5102.

- S. Mohanty, B. Punji, M. S. Balakrishna, Polyhedron, 2006, 25, 815-820.

- L. Botella, C. Najera, Angew. Chem., Int. Ed., 2002, 41,179-181.

- G. A. Grasa, A. C. Hillier, S. P. Nolan, Org. Lett., 2001, 3, 1077-1080.

- D. Suresh, M. S. Balakrishna, J. T. Mague, Tetrahedron Lett., 2007, 48, 2283-2285.

- J. L. Luche, Synthetic Organic Sonochemistry, Plenum Press, New York, 1998.

- W. Bonrath, Ultrason. Sonochem., 2003, 10, 55-59.

- T. J. Mason, J. P. Lorimer, Applied Sonochemistry: The Uses of Power Ultrasound in Chemistry and Processing, Wiley-VCH, 2002.

- G. V. Ambulgekar, S. D. Samant, A. B. Pandit, Ultrason. Sonochem., 2005, 12, 85-90.

- M. Atobe, M. Sasahira, T. Nonaka, Ultrason. Sonochem., 2000, 7, 103-107.

- R. Cella, H. A. Stefani, Tetrahedron Lett., 2006, 62, 5656-5662.

- K. Saïd, Y. Moussaoui, M. Kammoun, R. Ben Salem, Ultrason. Sonochem. 2011, 18, 23-27.

- M. Meciarova, M. Kiripolsky, S. Toma, Ultrason. Sonochem., 2005, 12, 401-403.

- R. R. Deshmukh, R. Rajagopal, K.V. Srinivasan, Chem.Commun., 2001, 1544-1545. 29 - T. J. Mason, Ed., Advances in Sonochemistry; JAI Press: London and Greenwich, 1990, Vol.1.

- Z. Zhang, Z. Zha, C. Gan, C. Pan, Y. Zhou, Z. Wang, M.M. Zhou, J. Org. Chem., 2006, 71, 4339-4342

- S. Tangestaninejad, M. Moghadam, V. Mirkhani, H. Kargar, Ultrason. Sonochem., 2006, 13, 32-36.

- A. Perosa, P. Tundo, M. Selva, S. Zinovyev, A. Testa, Org. Biomol. Chem., 2004, 2, 2249-2252.

- T. Jeffery, Tetrahedron, 1996, 52, 10113-10130.

- A. R. Hajipour, K. Karami, A. Pirisedigh, A. E. Ruoho, J. Organomet. Chem., 2009, 694, 2548-2554.

Downloads

Published

2011-05-18

Issue

Section

Organic Chemistry