3150
A. B. Naidu, G. Sekar / Tetrahedron Letters 49 (2008) 3147–3151
Table 3 (continued)
Entry
Aryl halide
Alcohol
nBuOH
Time (h)
24
Producta
Yieldb (%)
64
17
O2N
I
O2N
O
18
19
20
MeOH
30
28
14
75
57
82
I
OMe
I
OH
O
MeO
MeO
MeO
OH
I
O
MeO
21
22
MeOH
EtOH
12
11
24
88
70
63
Br
Br
Br
O2N
O2N
MeO
OMe
OEt
O2N
O2N
MeO
23
MeOH
OMe
a
All the alkyl aryl ethers gave satisfactory spectral data.
Isolated Yield.11
b
J.; Zhu, J. J. Am. Chem. Soc. 2002, 124, 583–590; (i) Kawata, S.;
Hirama, M. Tetrahedron Lett. 1998, 39, 8707–8710.
conditions for coupling. However, in the presence of the
BINAM–CuI catalyst even aryl bromides reacted with ali-
phatic alcohols to give good yields of the expected alkyl
aryl ethers without increasing the reaction temperature,
time or catalytic loading.
In summary, we have developed an efficient, experimen-
tally simple and economically attractive copper-catalyzed
O-arylation of aliphatic alcohols with aryl iodides and
bromides. Efforts to expand the utility of our new catalytic
system to other classes of nucleophiles will be reported in
due course.
2. For some recent reports on palladium-catalyzed aryl ether synthesis,
see (a) Vorogushin, A. V.; Huang, X.; Buchwald, S. L. J. Am. Chem.
Soc. 2005, 127, 8146–8149; (b) Kataoka, N.; Shelby, Q.; Stambuli, J.;
Hartwig, J. J. Org. Chem. 2002, 67, 5553–5566; (c) Kuwabe, S.;
Torraca, K. E.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 12202–
12206; (d) Prim, D.; Campagne, J.-M.; Joseph, D.; Andrioletti, B.
Tetrahedron 2002, 58, 2041–2075; (e) Hartwig, J. F. Angew. Chem.,
Int. Ed. 1998, 37, 2046–2067; (f) Palucki, M.; Wolfe, J. P.; Buchwald,
S. L. J. Am. Chem. Soc. 1997, 119, 3395–3396; (g) Torraca, K. E.;
Huang, X.; Parrish, C.; Buchwald, S. J. Am. Chem. Soc. 2001, 123,
10770–10771.
3. Shelby, Q.; Kataoka, N.; Mann, G.; Hartwig, J. J. Am. Chem. Soc.
2000, 122, 10718–10719.
Acknowledgements
4. Wolter, M.; Nordmann, G.; Job, G. E.; Buchwald, S. L. Org. Lett.
2002, 4, 973–976.
5. Hosseinzadeh, R.; Tajbakhsh, M.; Mohajerani, M.; Alikarami, M.
Synlett 2005, 1101–1104.
We thank DST, New Delhi for the financial support.
A.B.N. thanks UGC for a Senior Research fellowship.
6. (a) Manback, G. F.; Lipman, A. J.; Stockland, R. A., Jr.; Freidl, A.
L.; Hasler, A. F.; Stone, J. J.; Guzei, I. A. J. Org. Chem. 2005, 70,
244–250; (b) Xiao, X. Y.; Li, R.; Hurst, D.; Zhuang, H.; Shi, S.;
Czarnik, A. W.; Robichaud, A. J.; Wacker, D. A.; Robertson, D. W.
J. Comb. Chem. 2002, 4, 536–539.
7. Zhang, H.; Ma, D.; Cao, W. Synlett 2007, 243–246.
8. Altman, R. A.; Shafir, A. S.; Choi, A.; Lichtor, P. A.; Buchwald, S. L.
J. Org. Chem. 2008, 73, 284–286.
References and notes
1. (a) Yamazaki, N.; Washio, I.; Shibasaki, Y.; Mitsuru Ueda, M. Org.
Lett. 2006, 8, 2321–2324; (b) Asano, M.; Inoue, M.; Katoh, T. Synlett
2005, 2599–2602; (c) Jiang, H.; Leger, J.-M.; Huc, I. J. Am. Chem.
Soc. 2003, 125, 3448–3449; (d) Bolm, C.; Hildebrand, J. P.; Muniz,
˜
9. (a) Mannam, S.; Kumar, S. A.; Sekar, G. Adv. Synth. Catal. 2007,
349, 2253–2258; (b) Mannam, S.; Sekar, G. Tetrahedron Lett. 2008,
49, 1083–1086; (c) Mannam, S.; Sekar, G. Tetrahedron Lett. 2008, 49,
2457–2460.
10. Naidu, A. B.; Ragunath, O. R.; Prasad, D. J. C.; Sekar, G.
Tetrahedron Lett. 2008, 49, 1057–1061.
K.; Hermanns, N. Angew. Chem., Int. Ed. 2001, 40, 3284–3308; (e)
Gu, W. X.; Jing, X. B.; Pan, X. F.; Chan, A. S. C.; Yang, T. K.
Tetrahedron Lett. 2000, 41, 6079–6082; (f) Matsumoto, Y.; Uchida,
W.; Nakahara, H.; Yanagisawa, I.; Shibanuma, T.; Nohira, H. Chem.
Pharm. Bull. 2000, 48, 428; (g) Cao, B.; Park, H.; Joullie, M. M. J.
Am. Chem. Soc. 2002, 124, 520–521; (h) Temal-La¨ıb, T.; Chastanet,