Abstract
A series of Xantphos-based ligands containing various substituents in the diphenylphosphino groups were synthesized, and their effect on the product yield and ratio in the palladium-catalyzed arylation of ureas with nonactivated aryl halides was studied. The arylation of urea and phenylurea in the presence of Pd2(dba)3-CHCl3, 3,5-(CF3)2Xantphos, and Cs2CO3 in dioxane at 100°C gave the corresponding N,N'-diarylureas in 62-98% yield.
Similar content being viewed by others
REFERENCES
Vishnyakova, T.P., Golubeva, I.A., and Glebova, E.V. Usp. Khim., 1985, vol. 54, p. 429; Vyshnyakova, T.P., Golubeva, I.A., and Glebova, E.V., Russ. Chem. Rev. (Engl. Transl.), 1985, vol. 54, p. 249.
Schmidtchen, F.P. and Berger, M., Chem. Rev. 1997, vol. 97, p. 1609.
Okaniwa, M., Takeuchi, K., Asai, M., and Ueda, M., Macromolecules, 2002, vol. 35, p. 6224; Okaniwa, M., Takeuchi K., Asai, M., and Ueda, M., Macromolecules, 2002, vol. 35, p. 6232.
Tafesh, A.M. and Weiguny, J., Chem. Rev., 1996, vol. 96, p. 2035.
Mulla, S.A.R., Rode, C.V., Kelkar, A.A., and Gupte, S.P., J. Mol. Catal. A: Chem., 1997, vol. 122, p. 103.
Wolfe, J.P., Wagaw, S., Marcoux, J.-F., and Buchwald, S.L., Acc. Chem. Res., 1998, vol. 31, p. 805; Yang, B.H. and Buchwald, S.L., J. Organomet. Chem., 1999, vol. 576, p. 125; Hartwig, J.F., Angew. Chem., Int. Ed., 1998, vol. 37, p. 2046; Wolfe, J.P. and Buchwald, S.L., J. Org. Chem., 2000, vol. 65, p. 1144; Wolfe, J.P., Tomori, H., Sadighi, J.P., Yin, J., and Buchwald, S.L., J. Org. Chem., 2000, vol. 65, p. 1158.
Wolfe, J.P., Rennels, R.A., and Buchwald, S.L., Tetrahedron, 1996, vol. 52, p. 7525; He, F., Foxman, B.M., and Snider, B.B., J. Am. Chem. Soc., 1998, vol. 120, p. 6417; Yang, B.H. and Buchwald, S.L. Org. Lett., 1999, vol. 1, p. 35; Shakespeare, W.C., Tetrahedron Lett., 1999, vol. 40, p. 2035; Hartwig, J.F., Kawatsura, M., Hauck, S.I., Shaughnessy, K.H., and Alcazar-Roman, L.M., J. Org. Chem., 1999, vol. 64, p. 5575.
Yin, J. and Buchwald, S.L., Org. Lett., 2000, vol. 2, p. 1101.
Yin, J. and Buchwald, S.L., J. Am. Chem. Soc., 2002, vol. 124, p. 6043.
Cacchi, S., Fabrizi, G., Goggiamani, A., and Zappia, G., Org. Lett., 2001, vol. 3, p. 2539; Browning, R.G., Mahmud, H., Badarinarayana, V., and Lovely, C.J., Tetrahedron Lett., 2001, vol. 42, p. 7155.
Artamkina, G.A., Sergeev, A.G., and Beletskaya, I.P., Tetrahedron Lett., 2001, vol. 42, p. 4381; Artamkina, G.A., Sergeev, A.G., and Beletskaya, I.P., Russ. J. Org. Chem., 2002, vol. 38, p. 538.
Klapars, A., Huang, X., and Buchwald, S.L., J. Am. Chem. Soc., 2002, vol. 124, p. 7421.
Guari, Y., van Strijdonck, G.P.F., Boele, M.D.K., Reek, J.N.H., Kamer, P.C.J., and Leeuwen, P.W.N.M., Chem. Eur. J., 2001, vol. 7, p. 475.
Hartwig, J.F., Acc. Chem. Res., 1998, vol. 31, p. 852.
Kong, K.-C. and Cheng, C.-H., J. Am. Chem. Soc., 1991, vol. 113, p. 6313.
Collman, J.P., Hegedus, L.S., Norton, J.R., and Finke, R.G., Principles and Applications of Organotransition Metal Chemistry, Mill Valley, CA: University Science Books, 1987, p. 324.
Hartwig, J.F., Richards, S., Baranano, D., and Paul, F., J. Am. Chem. Soc., 1996, vol. 118, p. 3626.
Haman, B.C. and Hartwig, J.F., J. Am. Chem. Soc., 1998, vol. 120, p. 3694.
Ishii, Y., Ann. N.Y. Acad. Sci., 1972, vol. 239, p. 114; Ukai, T., Kawazura, H., and Ishii, Y., J. Organomet. Chem., 1974, vol. 65, p. 253.
Kranenburg, M., van der Burgt, Y.E.M., Kamer, P.C.J., and van Leeuwen, P.W.N.M., Organometallics, 1995, vol. 14, p. 3081; Hillebrand, S., Bruckmann, J., and Kruger, M.W., Tetrahedron Lett., 1995, vol. 36, p. 75.
Casalnuovo, A.L., Rajan Babu, T.V., Ayers, T.A., Warren, T.H., J. Am. Chem. Soc., 1994, vol. 117, p. 9869.
Magnelli, D.D., Tesi, G., Lowe, J.U., and McQuistion, W.E., Inorg. Chem., 1996, vol. 5, p. 457.
Peyron, L. and Peyron, J., Bull. Soc. Chim. Fr., 1953, p. 846.
Dieck, H.A., Laine, R.M., and Heck, R.F., J. Org. Chem., 1975, vol. 40, p. 2819.
Hoi, Ng.Ph.B., Xuong, Ng.D., and Suu, V.T., J. Chem. Soc., 1958, p. 2815.
Miyahara, M., Chem. Pharm. Bull., 1986, vol. 34, p. 1950.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Sergeev, A.G., Artamkina, G.A. & Beletskaya, I.P. Variation of Xantphos-Based Ligands in the Palladium-Catalyzed Reaction of Aryl Halides with Ureas. Russian Journal of Organic Chemistry 39, 1741–1752 (2003). https://doi.org/10.1023/B:RUJO.0000019738.50339.e8
Issue Date:
DOI: https://doi.org/10.1023/B:RUJO.0000019738.50339.e8