M. Lakshmi Kantam et al.
FULL PAPERS
The filtrate was concentrated and the residue was pu-
rified bycolumn chromatographyon silica gel
lier, J. F. Spindler, M. Taillefer, Chem. Eur. J. 2004, 10,
5
607.
[
10] a) H. Zhang, Q. Cai, D. Ma, J. Org. Chem. 2005, 70,
5164; b) Q. Cai, W. Zhu, H. Zhang, Y. Zhang, D. Ma,
Synthesis 2005, 496; c) D. Ma, Q. Cai, Synlett 2004, 128.
11] X. Lv, Z. Wang, W. Bao, Tetrahedron 2006, 62, 4756.
12] K. Okano, H. Tokuyama, T. Fukuyama, Org. Lett.
(
hexane/ethyl acetate, 70/30) to afford pure 1-(4-cya-
1
nophenyl)-1H-imidazole; mp: 152-1548C; H NMR
300 MHz, CDCl ): d=7.90 (br s, 1H), 7.79 (d, 2H,
(
3
[
[
J=8.3 Hz), 7.53 (d, 2H, J=8.3 Hz), 7.29 (br s, 1H),
7
1
1
.22 (br s, 1H); EI-MS: m/z=169 (100%), 142, 115,
2
003, 5, 4987.
02, 75, 50; IR: (KBr): n=2924.55, 2223.40, 1608.28,
[
[
13] C. Lamberth, J. Prakt. Chem. 1999, 341, 492.
14] a) D. A. Widdowson, R. Wilhelm, Chem. Commun.
À1
519.42, 1302.44, 1054.32, 834.11 cm .
2
003, 578; b) D. A. Widdowson, R. Wilhelm, Chem.
Commun. 1999, 2211; c) R. Wilhelm, D. A. Widdowson,
J. Chem. Soc., Perkin Trans. 1 2000, 22, 3808; d) Y. M.
Kim, S. Yu, J. Am. Chem. Soc. 2003, 125, 1696.
Acknowledgements
We wish to thankthe CSIR for financial support under the
TaskForce Project COR-0003. Jagjit Yadav and Soumi Laha
thankCSIR, India for their fellowships. Nanocrystalline CuO
samples were obtained from NanoScale Materials Inc., Man-
hattan, KS 66502, USA. Commercial CuO sample was pur-
chased from LOBA Chemie, India.
[
[
[
15] S. U. Son, I. K. Park, J. Park, T. Hyeon, Chem.
Commun. 2004, 778.
16] B. M. Choudary, Ch. Sridhar, M. L. Kantam, G. T. Ven-
kanna, B. Sreedhar, J. Am. Chem. Soc. 2005, 127, 9948.
17] a) Y. Jiang, S. Decker, C. Mohs, K. J. Klabunde, J.
Catal. 1998, 180, 24; b) E. Lucas, S. Decker, A. Khaleel,
A. Seitz, S. Fultz, A. Ponce, W. Li, C. Carnes, K. J. Kla-
bunde, Chem. Eur. J. 2001, 7, 2505.
References
[
18] a) R. Schlogl, S. B. Abd Hamid, Angew. Chem. Int. Ed.
2
004, 43, 1628; b) A. T. Bell, Science 2003, 299, 1688;
[
1] a) P. Cozzi, G. Carganico, D. Fusar, M. Grossoni, M.
Menichincheri, V. Pinciroli, R. Tonani, F. Vaghi, P. Sal-
vati, J. Med. Chem. 1993, 36, 2964; b) C. Almansa, J.
Bartroli, J. Belloc, F. L. Cavalcanti, R. Ferrando, L. A.
Gomez, I. Ramis, E. Carceller, M. Merlos, J. Garcia-
Rafanell, J. Med. Chem. 2004, 47, 5579.
c) B. M. Choudary, K. V. S. Ranganath, J. Yadav, M. L.
Kantam, Tetrahedron Lett. 2005, 46, 1369; d) M. L.
Kantam, K. B. Shiva Kumar, Ch. Sridhar Adv. Synth.
Catal. 2005, 347, 1212; e) B. M. Choudary, K. Mahen-
dar, K. V. S. Ranganath, J. Mol. Catal. A: Chem. 2005,
2
34, 25; f) M. L. Kantam, S. Laha, J. Yadav, B. M.
Choudary, B. Sreedhar, Adv. Synth. Catal. 2006, 348,
67; g) M. L. Kantam, S. Laha, J. Yadav, B. Sreedhar,
[
[
[
2] T. Güngçr, A. Fouquet, J. M. Teulon, D. Provost, M.
Cazes, A. Cloarec, J. Med. Chem. 1992, 35, 4455.
3] W. A. Herrmann, Angew. Chem. Int. Ed. 2002, 41,
8
Tetrahedron Lett. 2006, 47, 6213; h) B. M. Choudary, L.
Chakrapani, T. Ramani, K. V. Kumar, M. L. Kantam,
Tetrahedron 2006, 62, 9571; i) B. M. Choudary, K. Ma-
hendar, M. L. Kantam, K. V. S. Ranganath, T. Athar,
Adv. Synth. Catal. 2006, 348, 1977.
1
290.
4] a) G. I. Elliott, J. P. Konopelski, Org. Lett. 2000, 2,
055; b) P. Y. S. Lam, S. Deudon, K. M. Averill, R. H.
3
Li, M. Y. He, P. DeShong, C. G. Clark, J. Am. Chem.
Soc. 2000, 122, 7600; c) P. Y. S. Lam, C. G. Clark, S.
Saunern, J. Adams, K. M. Averill, D. M. T. Chan, A. P.
Combs, Synlett 2000, 674; d) J.-B. Lan, L. Chen, X.-Q.
Yu, J.-S. You, R.-G. Xie, Chem. Commun. 2004, 188.
5] a) A. S. Guram, S. L. Buchwald, J. Am. Chem. Soc.
[
19] a) P. Larsson, A. Andersson, J. Catal. 1998, 179, 72;
b) V. Chikan, A. Molnar, K. Balazsik, J. Catal. 1999,
1
84, 134; c) B. Raveau, C. Michel, M. Herview, D.
Groult, Crystal Chemistry of High-Tc Superconducting
Copper Oxides; Springer-Verlag: Berlin, 1991; d) C. P.
Poole, T. Datta, H. A. Farach, M. M. Rigney, C. R.
Sanders, Copper Oxide Superconductors; John Wiley&
Sons: NewYork, 1988.
[
1
994, 116, 7901; b) J. P. Wolfe, S. Wagaw, S. L. Buch-
wald, J. Am. Chem. Soc. 1996, 118, 7215; c) J. P. Wolfe,
S. Wagaw, J.-F. Marcoux, S. L. Buchwald, Acc. Chem.
Res. 1998, 31, 805; d) B. H. Yang, S. L. Buchwald, J. Or-
ganomet. Chem. 1999, 576, 125; e) K. W. Anderson,
R. E. Tundel, T. Ikawa, R. A. Altman, S. L. Buchwald,
Angew. Chem. Int. Ed. 2006, 45, 6523;.
[
20] a) Y. Liu, Q. Fu, M. F. Stephanopoulos, Catal. Today
2
004, 93-95, 241; b) A. Martinez-Arias, A. B. Hungria,
M. Fernandez-Garcia, J. C. Conesa, G. Munuera, J.
Phys. Chem. B 2004, 108, 17983; c) Z. Gu, K. L. Hohn,
Ind. Eng. Chem. Res. 2004, 43, 30.
[
6] G. Mann, J. F. Hartwig, M. S. Driver, C. Fernandez-
Rivas, J. Am. Chem. Soc. 1998, 120, 827.
[
21] a) B. M. Choudary, M. L. Kantam, K. V. S. Ranganath,
K. Mahendar, B. Sreedhar, J. Am. Chem. Soc. 2004,
126, 3396; b) B. M. Choudary, K. V. S. Ranganath, U.
Pal, M. L. Kantam, B. Sreedhar, J. Am. Chem. Soc.
2005, 127, 13167.
[
[
7] D.-Y. Lee, J. F. Hartwig, Org. Lett. 2005, 7, 1169.
8] a) J. C. Antilla, J. M. Baskin, T. E. Barder, S. L. Buch-
wald, J. Org. Chem. 2004, 69, 5578; b) J. C. Antilla, A.
Klapars, S. L. Buchwald, J. Am. Chem. Soc. 2002, 124,
1
1684.
[
9] a) H. J. Cristau, P. P. Cellier, J. F. Spindler, M. Taillefer,
[22] C. L. Carnes, J. Stipp, K. J. Klabunde, Langmuir 2002,
18, 1352.
Eur. J. Org. Chem. 2004, 695; b) H. J. Cristau, P. P. Cel-
1942
ꢀ 2007 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Adv. Synth. Catal. 2007, 349, 1938 – 1942