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2. (a) Kotschy, A.; Timari, G. Heterocycles from Transition
Metal Catalysis; Dordrecht: Springer, 2005; (b) Fyfe,
C. A. In The Chemistry of the Hydroxyl Group; Patai, S.,
Ed.; Wiley Interscience: New York, 1971; Vol. 1.
netic stirring. The consumption of ArX was judged by
TLC or GC analysis. The reaction was allowed to reach
room temperature, and dil HCl was carefully added. The
reaction mixture was extracted with diethyl ether and
purified by column chromatography on silica gel using
hexane/ethyl acetate as the solvent system.
3. For pertinent review for phenol synthesis, see: (a) George,
T.; Mabon, R.; Sweeney, G.; Sweeney, J. B.; Tavassoli, A.
J. Chem. Soc., Perkin Trans. 1 2000, 2529, and references
therein; (b) Hoarau, C.; Pettus, T. R. R. Synlett 2003, 127.
4. Fujimoto, K.; Tokuda, Y.; Maekawa, H.; Matsubara, Y.;
Mizuno, T.; Nishiguchi, I. Tetrahedron 1996, 52, 3889.
5. Maleczka, R. E.; Shi, F.; Holmes, D.; Smith, M. R., III. J.
Am. Chem. Soc. 2003, 125, 7792.
6. (a) Burgo, C. H.; Barder, T. E.; Huang, X.; Buchwald, S.
L. Angew. Chem., Int. Ed. 2006, 45, 4321; (b) Vorogushin,
A. B.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc.
2005, 127, 8146; (c) Kataoka, N.; Shelby, Q.; Stambuli, J.
P.; Hartwig, J. F. J. Org. Chem. 2002, 67, 5553; (d)
Torraca, K. E.; Huang, X.; Parrish, C.; Buchwald, S. L. J.
Am. Chem. Soc. 2001, 123, 10770; (e) Shelby, Q.; Kataoka,
N.; Mann, G.; Hartwig, J. F. J. Am. Chem. Soc. 2000, 122,
10718; (f) Metal-Catalyzed Cross-Coupling Reactions, 2nd
ed.; de Meijere, A., Diederich, F., Eds.; Wiley-VCH:
Weinheim, 2004.
2.3. General procedure of Table 3
ArX (1.0 mmol, if solid), Pd2dba3 (0.5 mol %), t-Bu3P
(2.0 mol %) and K3PO4ÆH2O were charged to a Schlenk
tube equipped with a magnetic stirbar. The tube was
evacuated and backfilled with nitrogen (3 cycles). Diox-
ane (2.0 mL) and ArX (1.0 mmol, if liquid) were added.
The tube was placed in a preheated oil bath with mag-
netic stirring. The consumption of ArX was judged by
TLC or GC analysis. To the crude reaction mixtures
was added water (ꢀ5 mL) and extracted with diethyl
ether. The crude product was purified by column chro-
matography on silica gel using hexane/ethyl acetate as
the solvent mixture.
7. For an alternative two-step synthesis of phenols, see:
Mann, G.; Incarvito, C.; Rheingold, A. L.; Hartwig, J. F.
J. Am. Chem. Soc. 1999, 121, 3224.
2.4. General procedure of Table 4
8. During the preparation of the manuscript, a closely related
and promising paper appeared. Anderson, K. W.; Ikawa,
T.; Tundel, R. E.; Buchwald, S. L. J. Am. Chem. Soc.
2006, 128, 10694–10695.
9. (a) Kwong, F. Y.; Lam, W. H.; Yeung, C. H.; Chan, K. S.;
Chan, A. S. C. Chem. Commun. 2004, 1922; (b) Kwong, F.
Y.; Yeung, C. H.; Chan, K. S.; Chan, A. S. C. Chem.
Commun. 2004, 2336; (c) Kwong, F. Y.; Lai, C. W.; Yu,
M.; Tan, D.-M.; Chan, A. S. C.; Chan, K. S. Organomet-
allics 2005, 24, 4170; (d) Kwong, F. Y.; Lai, C. W.; Chan,
K. S. J. Am. Chem. Soc. 2001, 123, 8864.
ArX (1.0 mmol, if solid), Pd2dba3 (0.5 mol %), t-Bu3P
(2.0 mol %) and K3PO4ÆH2O were charged into a
Schlenk tube equipped with a magnetic stirbar. The tube
was evacuated and backfilled with nitrogen (3 cycles).
Toluene (2.0 mL) and ArX (1.0 mmol, if liquid) were
added. The tube was placed in a preheated oil bath with
magnetic stirring. The consumption of ArX was judged
by TLC or GC analysis. The reaction was allowed to
reach room temperature. K2CO3 (2.0 mmol), water
(3.0 mmol), DMF (3.0 mmol) and alkyl halide
(2.0 mmol) were added. The reaction tube was re-sealed
and heated to 100 ꢁC for 3 h. The tube was cooled to
room temperature, and water (ꢀ5 mL) was added. The
crude mixture was extracted with diethyl ether and puri-
fied by column chromatography on silica gel.
´
´
10. Macıas, F. A.; Marın, D.; Oliveros-Bastidas, A.; Castel-
lano, D.; Simonet, A. M.; Molinillo, J. M. G. J. Agric.
Food Chem. 2005, 53, 538.
11. Altmann, E.; Cowan-Jacob, S. W.; Missbach, M. J. Med.
Chem. 2004, 47, 5833, and references therein.
12. For the synthesis of tert-butyl aryl ether from ArX with
NaOt-Bu, see: Parrish, C. A.; Buchwald, S. L. J. Org.
Chem. 2001, 66, 2498.
13. In fact, the electrophilic aryl halide is in situ transformed
to nucleophile in the presence of base/water, and react
with other electrophiles (for the two electrophilic compo-
nents coupling reaction).
14. Makosza, M.; Sienkiewicz, K. J. Org. Chem. 1990, 55,
4979.
15. Frixchkom, H.; Pintschovius, U.; Schinzel, E. Liebigs.
Ann. Chem. 1982, 1423.
16. Dwyer, C. L.; Holzapfel, C. W. Tetrahedron 1998, 54,
7843.
Acknowledgments
We thank the Research Grants Council of Hong Kong
(CERG: PolyU5006/05P) and The Hong Kong Poly-
technic University Internal Competitive Research Grant
(2005) for financial support. Special thanks to Professor
Albert S. C. Chan’s research group for instrumentation
support.
17. Sagar, A. D.; Tale, R. H.; Adude, R. N. Tetrahedron Lett.
2003, 44, 7061.
References and notes
18. Sargent, M. V.; Stransky, P. O. J. Chem. Soc., Perkin
Trans. 1 1982, 1605.
1. Tyman, J. H. P. Synthetic and Natural Phenols; Elsevier:
19. Quiroz, A.; Niemeyer, H. M. Heterocycles 1991, 32, 1681.
New York, 1996.