UREA AS AMMONIA EQUIVALENT IN ARYL HALIDES AMINATION
1689
3. Cioffi, C.L., Berlin, M.L., and Herr, R.J., Synlett., 2004, p. 841.
4. Jaime-Figueroa, S., Lui, Y., Muchowski, J.M., and Put-
man, D.G., Tetrahedron Lett., 1998, vol. 39, p. 1313.
5. Lim, C.W. and Lee, S.-G., Tetrahedron, 2000, vol. 56, p. 5131.
6. Hori, K. and Mori, M., J. Am. Chem. Soc., 1998, vol. 120,
p. 7651.
7. Lee, S., Jorgensen, M., and Hartwig, J.F., Org. Lett., 2001,
vol. 3, p. 2729.
8. Huang, X. and Buchwald, S.L., Org. Lett., 2001, vol. 3,
p. 3417.
9. Lee, D.-Y. and Hartwig, J.F., Org. Lett., 2005, vol. 7, p. 1169.
10. 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., Zh. Org. Khim., 2002,
vol. 38, p. 563.
11. Sergeev, A.G., Artamkina, G.A., and Beletskaya, I.P.,
Tetrahedron Lett., 2003, vol. 44, p. 4719; Sergeev, A.G.,
Artamkina, G.A., and Beletskaya, I.P., Zh. Org. Khim., 2003,
vol. 39, p. 1814.
p-MeC6H4CONHC6H4Me-p (identical by Rf with an
authentic sample). Conversion of initial aryl halide was
97%. Eluent petroleum ether, then a mixture EtOAc–
petroleum ether, 1:20, finally 1:40.
Reaction of urea with p-bromotrifluoro-
methylbenzene in the presence of L2. A mixture of
337 mg (1.50 mmol) of p-bromotrifluoromethylbenzene,
31.1 mg (0.517 mmol) of urea, 8.03 mg (7.75×10–3 mmol)
of Pd2dba3·CHCl3, 8.87 mg (2.25×10–2 mmol) of L2,
335 mg (2.98 mmol) of t-BuOK, and 4 ml of dioxane
was heated at 100°C for 23 h. Conversion of initial aryl
1
bromide was 92%. Yields (according to H NMR
spectra): 44% of p-(trifluoromethyl)phenyl tert-butyl ether
and 33% of m-(trifluoromethyl)phenyl tert-butyl ether.
The same products formed in a blank experiment on
heating at 100°C for 16 h a mixture of p-bromotrifluoro-
methylbenzene with t-BuOK in dioxane. p-(Trifluoro-
1
methyl)phenyl tert-butyl ether. H NMR spectrum
12. Harris, M.C. and Buchwald, S.L., J. Org. Chem., 2000,
vol. 65, p. 5327.
(dioxane), δ, ppm: 7.56 d (2H, J 8.5 Hz), 7.08 d (2H,
J 8.5 Hz), 1.38 s (9H). m-(Trifluoromethyl)phenyl tert-
13. Wolfe, J.P. and Buchwald, S.L., Angew. Chem. Int. Ed., 1999,
vol. 38, p. 2413; Wolfe, J.P., Tomori, H., Sadighi, J.P.,Yin, J.,
and Buchwald, S.L., J. Org. Chem., 2000, vol. 65, p. 1158.
14. Strieter, E.R., Blackmond, D.G., and Buchwald, S.L., J. Am.
Chem. Soc., 2003, vol. 125, p. 13978; Hartwig, J.F., Kawatsu-
ra, M., Hauck, S.I., Shaughnessy, K.H.,and Alcazar-
Roman, L.M., J. Org. Chem., 1999, vol. 64, p. 5575.
15. Sachinvala, N., Winsor, D.L., Maskos, K., Grimm, C.,
Hamed, O., Vigo, T.L., and Bertoniere, N.R., J. Org. Chem.,
2000, vol. 65, p. 9234.
16. Ishii, Y., Ann. N.-Y. Acad. Sci., 1972, vol. 239, p. 114; Ukai, T.,
Kawazura, H., Ishii, Y., Bonnet, J., and Ibers, J.A.,
J. Organometal. Chem., 1974, vol. 65, p.253.
17. 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., Kruger, C., and
Haenel, M.W., Tetrahedron Lett., 1995, vol. 36, p. 75.
18. Kuhn, R. and Krainer, H., Chem. Ber., 1952, vol. 85, p. 498.
19. Wieland, H., Ber., 1907, vol. 40, p. 4260.
1
butyl ether. H NMR spectrum (dioxane), δ, ppm:
7.39 t (1H, J 8 Hz), 7.35 d (1H, J 7.5 Hz), 7.26 s (1H),
7.18 d (1H, J 8 Hz ), 1.36 s (9 H).
REFERENCES
1. Hartwig, J.F., Synlett., 1997, p. 329; Hartwig, J.F., Angew.
Chem. Int. Ed., 1998, vol. 37, p. 2046;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., Organometal.
Chem., 1999, vol. 576, p. 125; Belfield,A.J., Brown, G.R., and
Foubister,A.J., Tetrahedron, 1999, vol. 55, p. 11399; Hart-
wig, J.F., Pure Appl. Chem., 1999, vol. 71, p. 1417;
Muci, A.R. and Buchwald, S.L., Top. Curr. Chem., 2002,
vol. 219, p. 131; Prim, D., Campagne, J.-M., Joseph, D., and
Andrioletti, B., Tetrahedron, 2002, vol. 58, p. 2041; Hart-
wig, J.F., in Handbook of Organopalladium Chemistry for
Organic Synthesis, Negishi, E., Ed., New York: Wiley-
Interscience, 2002, vol. 2, p. 1051.
2. Wolfe, J.P., Ahman, J., Sadighi, J.P., Singer, R.A., and
Buchwald, S.L., Tetrahedron Lett., 1997, vol. 38, p. 6367;
Mann, G., Hartwig, J.F., Driver, M.S., and Fernandez-
Rivas, C., J. Am. Chem. Soc., 1998, vol. 120, p. 827;
Singer, R.A. and Buchwald, S.L., Tetrahedron Lett., 1999,
vol. 40, p. 1095; Prashad, M., Hu, B., Lu, Y., Draper, R.,
Har, D., Repic, O., and Blacklock, J., J. Org. Chem., 2000,
vol. 65, p. 2612.
20. Cumper, C.W.N. and Thurston, A.P., J. Chem. Soc. B, 1971,
p. 422.
21. Bonhote, P., Moser, J.-E., Humphry-Baker, R., Vlacho-
poulos, N., Zakeeruddin, S.M., Walder, L., and Gratzel, M.,
J. Am. Chem. Soc., 1999, vol. 121, p. 1324.
22. Neugebauer, F.A.and Bamberger, S., Chem. Ber., 1974,
vol. 107, p. 2362.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 42 No. 11 2006