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LETTER
Synth. Catal. 2006, 348, 2197. (g) Lv, X.; Wang, Z.; Bao,
W. Tetrahedron 2006, 62, 4756.
(9) (a) Cristau, H. J.; Cellier, P. P.; Spindler, J. F.; Tailefer, M.
Chem. Eur. J. 2004, 10, 5607. (b)Kuil, M.; Bekedam, E. K.;
Visser, G. M.; van Leeuwen, P. W. N. M.; van Strijdonck,
G. P. F. Tetrahedron Lett. 2005, 46, 2405.
(10) (a) Rao, H.; Jin, Y.; Fu, H.; Jiang, Y.; Zhao, Y. Chem. Eur.
J. 2006, 12, 3636. (b) Rao, H.; Fu, H.; Jiang, Y.; Zhao, Y.
J. Org. Chem. 2005, 70, 8107. (c) Xu, L.; Zhu, D.; Wu, F.;
Wang, R.; Wan, B. Tetrahedron 2005, 61, 6553. (d) Zhang,
Z.; Mao, J.; Zhu, D.; Wu, F.; Chen, H.; Wan, B. Tetrahedron
2006, 62, 4435.
(11) Ma, H.; Jiang, X. J. Org. Chem. 2007, 72, 8943.
(12) Verma, A. K.; Singh, J.; Sankar, V. K.; Chaudhary, R.;
Chandra, R. Tetrahedron Lett. 2007, 48, 4207.
Preparation of L2a–2c
Benzaldehyde (10 mmol) and substituted urea (20 mmol)
were mixed with MeCN (5 mL) and stirred at r.t. for 5 h. The
corresponding product were furnished in quantitative yield
after removal of solvent.
Ligand L2a: 1H NMR (500 MHz, DMSO-d6): d = 7.31 (s,
4 H), 7.24 (s, 1 H), 6.63 (d, 2 H), 6.17 (s, 1 H), 5.96 (s, 2 H),
2.55 (s, 6 H). 13C NMR (125 MHz, DMSO-d6): d = 158.6,
143.8, 129.0, 127.9, 127.0, 60.3, 27.2. ESI-MS: 259 [M +
Na]+.
Preparation of L3
Paraformaldehyde (0.6 g) and acetamide (20 mmol) were
mixed in MeCN (5 mL), the mixture was refluxed at 110 °C
for 10 h to give L3 in 75% yield.
Ligand L3: 1H NMR (500 MHz, DMSO-d6): d = 6.44 (t,
2 H), 5.94 (s, 2 H), 4.22 (t, 2 H), 2.53 (d, 6 H). 13C NMR (125
MHz, DMSO-d6): d = 159.8, 47.0, 27.4. ESI-MS: 183 [M +
Na]+.
(13) Liu, L.; Frohn, M.; Xi, N.; Domingurez, C.; Hungate, R.;
Reider, P. J. J. Org. Chem. 2005, 70, 10135.
(14) Altman, R. A.; Buchwald, S. L. Org. Lett. 2006, 8, 2779.
(15) Lv, X.; Bao, W. J. Org. Chem. 2007, 72, 3863.
(16) Xie, Y.; Pi, S.; Wang, J.; Yin, D.; Li, J. J. Org. Chem. 2006,
71, 8324.
(17) Mino, T.; Harada, Y.; Shindo, H.; Sakamoto, M.; Fujita, T.
Synlett 2008, 614.
(18) (a) Zhu, L.; Cheng, L.; Zhang, Y.; Xie, R.; You, J. J. Org.
Chem. 2007, 72, 2737. (b) Zhu, L.; Guo, P.; Li, G.; Lan, J.;
Xie, R.; You, J. J. Org. Chem. 2007, 72, 8535.
General Experimental Procedure for the Arylation of
Azole
Azole (0.5 mmol), aromatic halide (0.5 mmol), CuI (10
mol%), ligand (10 mol%) and NaOMe (1 mmol) were
located in a flask with DMSO (1.5 mL). The mixture was
heated at the corresponding temperature for 12 h. The
reaction mixture was filtrated by SiO2 and extracted with
EtOAc (3 × 8 mL). The combined organic was concentrated
and subjected to SiO2 column to give target products.
Compound 3j: mp 247–250 °C. 1H NMR (500 MHz,
CDCl3): d = 7.94 (s, 1 H), 7.59 (d, 2 H), 7.52 (d, 2 H), 7.41–
7.37 (m, 4 H), 7.27 (s, 1 H), 7.19 (s, 1 H). 13C NMR (125
MHz, CDCl3): d = 139.7, 138.8, 136.8, 135.7, 132.3, 130.2,
128.8, 128.6, 122.4, 122.1, 118.6. ESI-MS: 299 [M + H]+.
Compound 4c(liquid): 1H NMR (500 MHz, CDCl3):
d = 8.60–8.57 (m, 2 H), 8.06 (t, 1 H), 7.88–7.85 (m, 2 H),
(19) Preparation of Ligands L1a–c
Benzaldehyde (10 mmol) and the corresponding amide (20
mmol) were added to the vessel with 5 mL MeCN (5 mL),
and TMSCl (30 mol%) was applied as catalyst. The mixture
was refluxed for 8 h. The crude product precipitated from the
solution. The analytical pure product was obtained in 94%,
78%, and 92% yield, respectively, by washing with MeCN
(3 mL).
Ligand L1a: 1H NMR (500 MHz, DMSO-d6): d = 8.50 (d,
7.55 (d, 1 H), 7.38–7.35 (m, 2 H), 7.29–7.26 (m, 1 H). 13
C
NMR (125 MHz, CDCl3): d = 150.0, 149.6, 144.8, 141.5,
139.1, 132.3, 124.4, 123.5, 122.0, 120.8, 114.5, 112.8. ESI-
MS: 196 [M + H]+.
2 H), 7.38–7.27 (m, 5 H), 6.52 (t, 1 H), 1.86 (s, 6 H). 13
C
NMR (125 MHz, DMSO-d6): d = 169.5, 141.5, 129.2, 128.4,
127.3, 58.2, 23.4. ESI-MS: m/z = 229 [M + Na]+.
Synlett 2008, No. 19, 3068–3072 © Thieme Stuttgart · New York