Recoverable Palladium(0) on Poly(vinylpyrrolidone) Catalyzed Ligand-free Suzuki Reaction in Water
Lei Wang
Department of Chemistry, Huaibei Coal Teacher College, Huaibei, Anhui 235000, China
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Project supported by the National Natural Science Foundation of China (No. 20372024), the Excellent Scientist Foundation of Anhui Province, China (No. 04046080), the Scientific Research Foundation for the Returned Overseas Chinese Scholars, the Ministry of Education of China (No. 2002247), the Excellent Young Teacher Program of the Ministry of Education of China (No. 2024) and the Key Project of Science and Technology of the Ministry of Education of China (No. 0204069).
Search for more papers by this authorLei Wang
Department of Chemistry, Huaibei Coal Teacher College, Huaibei, Anhui 235000, China
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Project supported by the National Natural Science Foundation of China (No. 20372024), the Excellent Scientist Foundation of Anhui Province, China (No. 04046080), the Scientific Research Foundation for the Returned Overseas Chinese Scholars, the Ministry of Education of China (No. 2002247), the Excellent Young Teacher Program of the Ministry of Education of China (No. 2024) and the Key Project of Science and Technology of the Ministry of Education of China (No. 0204069).
Search for more papers by this authorAbstract
In the absence of any ligand, a recoverable palladium(0) on poly(vinylpyrrolidone) (PVP) catalyzed Suzuki reaction of aryl iodide and bromide with potassium aryltrifluoroborate was developed. The reaction conditions involved the use of water as the solvent, potassium carbonate as the base, and PVP supported palladium metal colloids as the catalyst. The palladium metal could be recovered and recycled for eight consecutive trials without significant loss of its activity.
REFERENCES
- 1 Miyaura, N.; Suzuki, A.. Chem. Rev., 1995, 95, 2457.
- 2 Suzuki, A.. J. Organomet. Chem., 1999, 576, 147.
- 3 Wolfe, J. P.; Singer, R. A.; Yang, B. H.; Buchwald, S. L.. J. Am. Chem. Soc., 1999, 121, 9550.
- 4 Brown, H. C., Organic Syntheses via Boranes, John, Wiley and Sons, New York, 1975.
- 5 Hajduk, P. J.; Bures, M.; Praestgaard, J.; Fesik, S. W.. J. Med. Chem., 2000, 43, 3443.
- 6 Benbow, J. W.; Martinez, B. L.. Tetrahedron Lett., 1996, 37, 8829.
- 7 Zhang, H.; Kwong, F. Y.; Tian, Y.; Chan, K. S.. J. Org. Chem., 1998, 63, 6886.
- 8 Snieckus, V.; Wong, P. L.; Nguyen, T.; Guillaneux, D.; Bower, J. F.. J. Org. Chem., 1998, 63, 1514.
- 9 Malleron, J.; Fiaud, J.; Legros, J., Handbook of Palladium- catalyzed Organic Reactions, Academic Press, San Diego, CA, 1997.
- 10
Suzuki, A., Metal-catalyzed Cross-coupling Reactions, Eds.: F. Diederich; P. J. Stang, VCH, Weinheim, 1998, pp. 49–97.
10.1002/9783527612222 Google Scholar
- 11 Alo, B. I.; Kandil, A.; Patil, P. A.; Sharp, M. J.; Siddiqui, M. A.; Snieckus, V.; Josephy, P. D.. J. Org. Chem., 1991, 56, 3763.
- 12 Wallow, T. I.; Novak, B. M.. J. Org. Chem., 1994, 59, 5034.
- 13 Genet, J. P.; Linquist, A.; Blart, E.; Mouries, V.; Savignac, M.. Tetrahedron Lett., 1995, 36, 1443.
- 14 Genet, J. P.; Savignac, M.. J. Organomet. Chem., 1999, 576, 305.
- 15 Marck, G.; Villiger, A.; Buchecker, R.. Tetrahedron Lett., 1994, 35, 3277.
- 16 LeBlond, C. R.; Andrews, A. T.; Sowa, J. R.Jr.; Sun, Y.. Org. Lett., 2001, 3, 1555.
- 17 Tagata, T.; Nishida, M.. J. Org. Chem., 2003, 68, 9412.
- 18 Kabalka, G. W.; Pagni, R. M.; Hair, C. M.. Org. Lett., 1999, 1, 1423.
- 19 Kabalka, G. W.; Namboodiri, V.; Wang, L.. Chem. Commun., 2001, 775.
- 20 Choudary, B. M.; Madhi, S.; Chowdari, N. S.; Kantam, M. L.; Sreedhar, B.. J. Am. Chem. Soc., 2002, 124, 14127.
- 21 Li, C. J.; Chan, T. H., Organic Reactions in Aqueous Media, Wiley, New York, 1997.
- 22 Lindstrom, U. M.. Chem. Rev., 2002, 102, 2751 and references cited therein.
- 23 Reetz, M. T.; Helbig, W.; Quaiser, S. A.; Stimming, U.; Breuer, N.; Vogel, R.. Science, 1995, 267, 367.
- 24
Reetz, M. T.;
Winter, M.;
Breinbauer, R.;
Thurn-Albrecht, T.;
Vogel, W..
Chem. Eur. J.,
2001,
7,
1084.
10.1002/1521-3765(20010302)7:5<1084::AID-CHEM1084>3.0.CO;2-J CAS PubMed Web of Science® Google Scholar
- 25
Reetz, M. T.;
Westermann, E..
Angew. Chem., Int. Ed.,
2000,
39,
165.
10.1002/(SICI)1521-3773(20000103)39:1<165::AID-ANIE165>3.0.CO;2-B CAS PubMed Web of Science® Google Scholar
- 26 Reetz, M. T.; Vries, J. G.. Chem. Commun., 2004, 1559.
- 27 Bradley, J. S.; Millar, J. M.; Hill, E. W.. J. Am. Chem. Soc., 1991, 113, 4016.
- 28 Narayanan, R.; EI-Sayed, M. A.. J. Am. Chem. Soc., 2003, 125, 8340.
- 29 Li, Y.; Hong, X. M.; Collard, D. M.; EI-Sayed, M. A.. Org. Lett., 2000, 2, 2385.
- 30 Li, P.; Wang, L.; Li, H.. Tetrahedron, 2005, 61, 8633.
- 31 Molander, G. A.; Ribagorda, M.. J. Am. Chem. Soc., 2003, 125, 11148.
- 32 Molander, G. A.; Rivero, M. R.. Org. Lett., 2002, 4, 107.
- 33 Thadani, A. N.; Batey, R. A.. Org. Lett., 2002, 4, 3827.
- 34 Newman, M. S.; Eberwein, J. A.. J. Org. Chem., 1964, 29, 2516.
- 35 Eisch, J. J.; Hallenbeck, L. E.; Han, K. I.. J. Am. Chem. Soc., 1968, 108, 7763.
- 36 Badone, D.; Baroni, M.; Cardamone, R.; Ielmini, A.; Guzzi, U.. J. Org. Chem., 1997, 62, 7170.
- 37 Hermann, E. C.; Hoyer, G. A.; Kelm, J.. Spectrochim. Acta, Part A, 1982, 38, 1057.
- 38 Kabalka, G. W.; Wang, L.; Pagni, R. M.; Hair, C. M.; Namboodiri, V.. Synthesis, 2003, 217.
- 39 Bei, X.; Turner, H. W.; Weinberg, W. H.; Guram, A. S.. J. Org. Chem., 1999, 64, 6797.
- 40 Hendrickson, J. B.; Wolf, W. A.. J. Org. Chem., 1968, 33, 3610.
- 41 Dewar, M. J. S.; Hart, L. S.. Tetrahedron, 1970, 26, 1001.
- 42 Klemm, L. H.; Stevens, M. P.; Tran, L. K.; Sheley, J.. J. Heterocycl. Chem., 1988, 25, 1111.
- 43 Miles, P.; Suschitzky, H.. Tetrahedron, 1963, 19, 385.
- 44 Patrick, T. B.; Willaredt, R. P.; DeGonia, D. J.. J. Org. Chem., 1985, 50, 2232.