8886
M. Kidwai et al. / Tetrahedron Letters 48 (2007) 8883–8887
than those with electron-withdrawing groups (Table 4,
entries 3 and 4).
Kuwabe, S. I.; Torraca, K. E.; Buchwald, S. L. J. Am.
Chem. Soc. 2001, 123, 12202–12206.
5. (a) Hartwig, J. F. Acc. Chem. Res. 1998, 31, 853; (b)
Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046–
1
In conclusion, a novel, easy, and economical method for
the synthesis of diaryl ethers has been developed using
Cu-np as a catalyst. The process is simple and allows
the formation of a diverse range of diaryl ethers in excel-
lent yields. Overall, this methodology offers competitive
advantages such as recyclability of the catalyst without
further purification or without using additives or cofac-
tors, low catalyst loading, broad substrate applicability,
and high yields in short reaction times.
2
067.
1
1
6. Mann, G.; Incarvito, C.; Rheingold, A. L.; Hartwig, J. F.
J. Am. Chem. Soc. 1999, 121, 3224–3225.
7. (a) Evans, D. A.; Katz, J. L.; West, T. R. Tetrahedron
Lett. 1998, 39, 2937–2940; (b) Decicco, C.; Song, P. S.;
Evans, D. A. Org. Lett. 2001, 3, 1029–1032.
18. Chan, D. M. T.; Monaco, K. L.; Wang, R.; Winters, M. P.
Tetrahedron Lett. 1998, 39, 2933–2936.
1
9. (a) Loupy, A.; Pelit, A.; Hamelin, J.; Texier-Boullet, F.;
Jacquault, P.; Mathe, D. Synthesis 1998, 1213–1234; (b)
Varma, R. S. Green Chem. 1999, 1, 43–55; (c) Varma, R. S.
Pure Appl. Chem. 2001, 73, 193–198; (d) Lidstrom, P.;
Tierney, J.; Wathey, B.; Westman, J. Tetrahedron 2001, 57,
Acknowledgment
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225–9283.
0. (a) Finta, Z.; Hell, Z.; Toke, L. J. Chem. Res. (S) 2000,
42–244; (b) Wang, J.-X.; Liu, Z.; Hu, Y.; Wei, B.; Bai, L.
S.M. gratefully acknowledges financial support from the
Department of Science and Technology, Government of
India, for this work.
2
2
J. Chem. Res. (S) 2000, 484–485; (c) Chatti, S.; Bortolussi,
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1. In a 50 mL round bottom flask, the phenol (1 mmol), aryl
halide (1 mmol), and Cs
2 3 3
CO (1.5 mmol) in CH CN
(
5 mL) were stirred under a nitrogen atmosphere and
121, 4369–4378; (b) Widenhoefer, R. A.; Zhong, H. A.;
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reaction mixture was allowed to stir at 50–55 °C for the
appropriate time (Table 4). The extent of reaction was
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1
0 °C for 5 min. The organic layer was decanted and
(
d) Wolfe, J. P.; Tomori, H.; Sadighi, J. P.; Yin, J.;
the remaining Cu-nanoparticles were reused for further
Buchwald, S. L. J. Org. Chem. 2000, 65, 1158–1174; (e)