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LETTER
2-(2,6-Dichloro-4-methylphenyl)pyridine (2b)10
2517. (d) Kawano, T.; Matsuyama, N.; Hirano, K.; Satoh,
T.; Miura, M. J. Org. Chem. 2010, 75, 1764. (e) Yotphan,
S.; Bergman, R. G.; Ellman, J. A. Org. Lett. 2009, 11, 1511.
(f) Li, C.-J. Acc. Chem. Res. 2009, 42, 335.
Oil; 30% yield. 1H NMR (400 MHz, CDCl3): d = 2.30 (s, 3 H), 7.16
(s, 2 H), 7.31–7.35 (m, 2 H), 7.73 (td, J = 1.6, 7.6 Hz, 1 H), 8.68 (d,
J = 4.8 Hz, 1 H). IR (KBr): n = 2923, 1731, 1600, 1494, 1452, 736,
696 cm–1. MS (EI): m/z = 241.0 [M+ (37Cl37Cl)] (3.10), 239.0 [M+
(37Cl35Cl)] (19.70), 237.0 [M+ (35Cl35Cl)] (30.51), 205.0, 204.0,
202.0, 167.1, 166.1, 139.1, 138.0.
(3) For representative examples of the copper-catalyzed C–
heteroatom bond formation, see: (a) Kawano, T.; Hirano,
K.; Satoh, T.; Miura, M. J. Am. Chem. Soc. 2010, 132, 6900.
(b) Zhang, L. N.; Ang, G. Y.; Chiba, S. Org. Lett. 2010, 12,
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Luo, F.; Zhang, S. H.; Cheng, J. J. Org. Chem. 2010, 75,
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M.; Ribas, X.; Stahl, S. S. J. Am. Chem. Soc. 2010, 132,
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(4) (a) Ullmann’s Encyclopedia of Industrial Chemistry, 6th ed.;
Wiley-VCH: Weinheim, 2002. (b) Davos, S. G.
Organotransition Metal Chemistry: Application to Organic
Synthesis; Pergamon Press: Oxford, 1982.
Supporting Information for this article is available online at
Primary Data for this article are available online at http://
using the following DOI: 10.4125/pd0009th. FID data and associat-
ed files for the 1H and 13C NMR spectra are available.
(5) (a) Sasson, Y. In The Chemistry of Functional Group: The
Chemistry of Halides, Pseudo-halides and Azides, Part 1,
Suppl. D2; Patai, S.; Rappoport, Z., Eds.; John Wiley and
Sons: Chichester, 1995. (b) de la Mare, P. D. B.
Electrophilic Halogenation; Cambridge University Press:
New York, 1976.
Acknowledgment
This work was supported by the National Natural Sciences Found-
ation of China (20852004, 20902058), Shanghai Pujiang Program
(09PJ1408100), Shanghai Education Committee (ssd09018), and
Shanghai Jiao Tong University.
(6) Wan, X. B.; Ma, Z. X.; Li, B. J.; Zhang, K. Y.; Cao, S. K.;
Zhang, S. W.; Shi, Z. J. J. Am. Chem. Soc. 2006, 128, 7416.
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Synlett 2011, No. 7, 1038–1042 © Thieme Stuttgart · New York