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C-C Cross-Coupling Reactions by Palladium on Barium and Potassium Polyoxotungstate Supports
Corresponding Author(s) : I. Karume
Asian Journal of Chemistry,
Vol. 30 No. 10 (2018): Vol 30 Issue 10, 2018
Abstract
A heterogeneous catalyst system for Suzuki and Heck coupling reactions was developed using polyoxometalates as supports for palladium. The catalyst system was synthesized in a one step process using sodium phosphotungstate and palladium acetate. We used the supported catalyst in organic media without the need for special ligands. Substantial activity was observed after several recycles. The catalyst showed high product selectivity with yields up to > 95 % in both Suzuki and Heck reactions.
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- N. Miyaura, K. Yamada and A. Suzuki, Tetrahedron Lett., 20, 3437 (1979); https://doi.org/10.1016/S0040-4039(01)95429-2.
- N. Miyaura and A.J. Suzuki, Chem. Soc. Chem. Commun., 19, 866 (1979); https://doi.org/10.1039/c39790000866.
- T. Jeffery and M. David, Tetrahedron Lett., 39, 5751 (1998); https://doi.org/10.1016/S0040-4039(98)01135-6.
- J. Pierre Genet and M. Savignac, J. Organomet. Chem., 576, 305 (1999); https://doi.org/10.1016/S0022-328X(98)01088-2.
- R.R. Deshmukh, R. Rajagopal and K.V. Srinivasan, Chem. Commun., 17, 1544 (2001); https://doi.org/10.1039/b104532f.
- E.H. Rahim, F.S. Kamounah, J. Frederiksen and J.B. Christensen, Nano Lett., 1, 499 (2001); https://doi.org/10.1021/nl015574w.
- S. Pathak, M.T. Greci, R.C. Kwong, K. Mercado, G.K.S. Prakash, G.A. Olah and M.E. Thompson, Chem. Mater., 12, 1985 (2000); https://doi.org/10.1021/cm0001556.
- C. Rocaboy and J.A. Gladysz, Org. Lett., 4, 1993 (2002); https://doi.org/10.1021/ol025790r.
- B.I. Alo, A. Kandil, P.A. Patil, M.J. Sharp, M.A. Siddiqui, V. Snieckus and P.D. Josephy, J. Org. Chem., 56, 3763 (1991); https://doi.org/10.1021/jo00012a004.
- Y. Li, M.X. Hong, M.D. Collard and A.M. El-Sayed, Org. Lett., 2, 2385 (2000); https://doi.org/10.1021/ol0061687.
- S. Wang, Z. Wang and Z. Zha, Dalton Trans., 9363 (2009); https://doi.org/10.1039/b913539a.
- J. Hu and Y. Liu, Langmuir, 21, 2121 (2005); https://doi.org/10.1021/la0471902.
- N.T.S. Phan, M. Van Der Sluys and C.W. Jones, Adv. Synth. Catal., 348, 609 (2006); https://doi.org/10.1002/adsc.200505473.
- R. Contant and G. Herveb, Rev. Inorg. Chem., 22, 63 (2002); https://doi.org/10.1515/REVIC.2002.22.2.63.
- J.E. Toth and F.C. Anson, J. Am. Chem. Soc., 111, 2444 (1989); https://doi.org/10.1021/ja00189a012.
- C.L. Hill and C.M. Prosser-McCartha, Coord. Chem. Rev., 143, 407 (1995); https://doi.org/10.1016/0010-8545(95)01141-B.
References
N. Miyaura, K. Yamada and A. Suzuki, Tetrahedron Lett., 20, 3437 (1979); https://doi.org/10.1016/S0040-4039(01)95429-2.
N. Miyaura and A.J. Suzuki, Chem. Soc. Chem. Commun., 19, 866 (1979); https://doi.org/10.1039/c39790000866.
T. Jeffery and M. David, Tetrahedron Lett., 39, 5751 (1998); https://doi.org/10.1016/S0040-4039(98)01135-6.
J. Pierre Genet and M. Savignac, J. Organomet. Chem., 576, 305 (1999); https://doi.org/10.1016/S0022-328X(98)01088-2.
R.R. Deshmukh, R. Rajagopal and K.V. Srinivasan, Chem. Commun., 17, 1544 (2001); https://doi.org/10.1039/b104532f.
E.H. Rahim, F.S. Kamounah, J. Frederiksen and J.B. Christensen, Nano Lett., 1, 499 (2001); https://doi.org/10.1021/nl015574w.
S. Pathak, M.T. Greci, R.C. Kwong, K. Mercado, G.K.S. Prakash, G.A. Olah and M.E. Thompson, Chem. Mater., 12, 1985 (2000); https://doi.org/10.1021/cm0001556.
C. Rocaboy and J.A. Gladysz, Org. Lett., 4, 1993 (2002); https://doi.org/10.1021/ol025790r.
B.I. Alo, A. Kandil, P.A. Patil, M.J. Sharp, M.A. Siddiqui, V. Snieckus and P.D. Josephy, J. Org. Chem., 56, 3763 (1991); https://doi.org/10.1021/jo00012a004.
Y. Li, M.X. Hong, M.D. Collard and A.M. El-Sayed, Org. Lett., 2, 2385 (2000); https://doi.org/10.1021/ol0061687.
S. Wang, Z. Wang and Z. Zha, Dalton Trans., 9363 (2009); https://doi.org/10.1039/b913539a.
J. Hu and Y. Liu, Langmuir, 21, 2121 (2005); https://doi.org/10.1021/la0471902.
N.T.S. Phan, M. Van Der Sluys and C.W. Jones, Adv. Synth. Catal., 348, 609 (2006); https://doi.org/10.1002/adsc.200505473.
R. Contant and G. Herveb, Rev. Inorg. Chem., 22, 63 (2002); https://doi.org/10.1515/REVIC.2002.22.2.63.
J.E. Toth and F.C. Anson, J. Am. Chem. Soc., 111, 2444 (1989); https://doi.org/10.1021/ja00189a012.
C.L. Hill and C.M. Prosser-McCartha, Coord. Chem. Rev., 143, 407 (1995); https://doi.org/10.1016/0010-8545(95)01141-B.