3
446
H. He, Y.-J. Wu / Tetrahedron Letters 44 (2003) 3445–3446
Table 1. Arylation of phenols with aryl halides
In summary, we have developed an operationally sim-
ple and efficient method for the copper-catalyzed cou-
pling of a variety of aryl bromides and iodides with
12
phenols using microwave heating.
References
1
. Pell o´ n, R. F.; Carrasco, R.; Mili a´ n, V.; Rodes, L. Synth.
Commun. 1995, 25, 1077–1083 and references cited therein.
. For examples of biologically important diaryl ethers, see:
Evans, D. A.; DeVries, K. M. In Glycopeptide Antibiotics,
Drugs and the Pharmaceutical Sciences; Nagarajan, R., Ed.;
Marcel Decker: New York, 1994; Vol. 63, pp. 63–104.
. (a) Ullmann, F. Chem. Ber. 1904, 37, 853; (b) Lindley, J.
Tetrahedron 1984, 40, 1433–1456.
2
3
4
5
. Chan, D. M. T.; Winters, M. P.; Monaco, K. L.; Wang,
R. Tetrahedron Lett. 1998, 39, 2933–2936.
. (a) Evans, D. A.; Katz, J. L.; West, T. R. Tetrahedron Lett.
1
998, 39, 2937–2940; (b) Decicco, C. P.; Song, S.; Evans,
D. A. Org. Lett. 2001, 3, 1029–1032.
6
7
8
. Lam, P. Y. S.; Vincent, G.; Clark, C.; Deudon, S.; Jadhav,
P. K. Tetrahedron Lett. 2001, 42, 3415–3418.
. Marcoux, J.; Doye, S.; Buchwald, S. L. J. Am. Chem. Soc.
1997, 119, 10539–10540.
. Aranyos, A.; Old, D. W.; Kiyomori, A.; Wolfe, J. P.;
Sadighi, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1999,
121, 4369–4378.
9. Perreux, L.; Loupy, A. Tetrahedron 2001, 57, 9199–9223.
1
1
1
0. For a copper(II)-mediated N-arylation of NꢀH containing
heteroarenes with arylboronic acids under microwave
irradiation, see: Combs, A. P.; Saubern, S.; Rafalski, M.;
Lam, P. Y. S. Tetrahedron Lett. 1999, 40, 1623–1626.
1. For a microwave-assisted Goldberg reaction, see: Lange,
J. H. M; Hofmeyer, L. J. F.; Hout, F. A. S.; Osnabrug,
S. J. M.; Verveer, P. C.; Kruse, C. G.; Feenstra, R.
Tetrahedron Lett. 2002, 43, 1101–1104.
2. Representative procedure: To a solution of 1-iodo-4-tert-
butylbenzene (130 mg, 0.5 mmol) and phenol (94 mg, 1
mmol) in NMP (0.67 mL) in a microwave vial were added
cesium carbonate (325 mg, 1 mmol), and copper (I) iodide
(
9.5 mg, 0.05 mmol). The vial was sealed and heated in a
®
Smith Creator at 195°C for 2 h. The temperature of the
contents of the vessel was monitored using a calibrated
infrared temperature control mounted under the reaction
vessel. The cooled reaction mixture was passed through a
2
4
g silica gel cartridge eluting with hexanes to give
-phenoxy-tert-butylbenzene (102 mg, 90%) as a colorless
1
oil. H NMR (CDCl , 400 MHz) l 7.29–7.35 (4H, m), 7.07
3
13
(
1H, m), 7.00 (2H, m), 6.93 (2H, m), and 1.31 (s, 9H);
C
NMR (CDCl , 100 MHz) l 157.6, 154.7, 146.1, 129.6, 126.5,
3
1
22.9, 118.6, 118.5, 34.3, and 31.5. The spectroscopic data
7
is in full agreement with that described in the literature.