The effect of ultrasound on the yields of Heck reaction using Pd-catalyst in DMF/water
DOI:
https://doi.org/10.13171/mjc.1.1.2011.18.05.12Abstract
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
Issue
Section
License
Authors who publish with this journal agree to the following terms:- Authors retain copyright and grant the journal right of first publication with the work simultaneously licensed under a Creative Commons Attribution License that allows others to share the work with an acknowledgement of the work's authorship and initial publication in this journal
- Authors are able to enter into separate, additional contractual arrangements for the non-exclusive distribution of the journal's published version of the work (e.g., post it to an institutional repository or publish it in a book), with an acknowledgement of its initial publication in this journal
- Authors are permitted and encouraged to post their work online (e.g., in institutional repositories or on their website) prior to and during the submission process, as it can lead to productive exchanges, as well as earlier and greater citation of published work (See The Effect of Open Access).