An advantageous ligand-free protocol for Suzuki couplings is described. The synthetic procedure entails microwave irradiation for the reduction of the reaction times and the use of silica cartridges for the purification. Dihalo-pyrimidine structures, interesting scaffolds in medicinal chemistry, were chosen as test compounds.

References and Notes

2a Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457–2483.
10.1021/cr00039a007
CAS Web of Science® Google Scholar
2b Suzuki, A. Chem. Commun. 2005, 4759–4763.
Google Scholar
3 5-Bromo-2-hydroxy-pyrimidine can be prepared as reported by Vlad, G.; Horvath, I. T. J. Org. Chem. 2002, 67, 6550–6552, or purchased from common providers.
10.1021/jo0255781
CAS PubMed Web of Science® Google Scholar
4 Some recent papers involving potassium fluoride as base in Suzuki couplings: (a) Kabalka, G. W.; Namboodiri, V.; Wang, L. Chem. Commun. 2001, 775.
Google Scholar
4b Basu, B.; Das, P.; Bhuiyan, Md. M. H.; Jha, S. Tetrahedron Lett. 2003, 44, 3817–3820.
10.1016/S0040-4039(03)00731-7
CAS Web of Science® Google Scholar
4c Kabalka, G. W.; Wang, L.; Pagni, R. M.; Hair, C. M.; Namboodiri, V. Synthesis 2003, 217–222.
Google Scholar
4d Song, C.; Ma, Y.; Chai, Q.; Ma, C.; Jiang, W.; Andrus, M. B. Tetrahedron 2005, 61, 7438–7446.
10.1016/j.tet.2005.05.071
CAS Web of Science® Google Scholar
5 Some recent papers involving palladium(II) acetate as catalyst in Suzuki couplings: (a) Leadbeater, N. E.; Marco, M. Org. Lett. 2002, 4, 2973–2976.
10.1021/ol0263907
CAS PubMed Web of Science® Google Scholar
5b Deng, Y.; Gong, L.; Mi, A.; Liu, H.; Jiang, Y. Synthesis 2003, 337–339.
Google Scholar
5c Klingensmith, L. M.; Leadbeater, N. E. Tetrahedron Lett. 2003, 44, 765–768.
10.1016/S0040-4039(02)02645-X
CAS Web of Science® Google Scholar
5d Liu, W.-J.; Xie, Y.-X.; Liang, Y.; Li, J.-H. Synthesis 2006, 860–864.
Google Scholar
6 Schomaker, J. M.; Delia, T. J. J. Org. Chem. 2001, 66, 7125–7128.
10.1021/jo010573+
CAS PubMed Web of Science® Google Scholar
7 Delia, T. J.; Schomaker, J. M.; Kalinda, A. S. J. Heterocycl. Chem. 2006, 43, 127–131.
10.1002/jhet.5570430119
CAS Web of Science® Google Scholar
8 Coppola, G. M.; Hardtmann, G. E.; Huegi, B. S. J. Heterocycl. Chem. 1980, 17, 1479–1482.
10.1002/jhet.5570170724
CAS Web of Science® Google Scholar
9 Brown, D. J.; Lee, T.-C. J. Chem. Soc. (C) 1970, 214–219.
Google Scholar

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Volume45, Issue4

July/August 2008

Pages 1077-1081

Simple microwave-assisted ligand-free suzuki cross-coupling: Functionalization of halo-pyrimidine moieties

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Simple microwave-assisted ligand-free suzuki cross-coupling: Functionalization of halo-pyrimidine moieties

Abstract

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