2084
X.-Q. Zhang, Z.-X. Wang
LETTER
J. Am. Chem. Soc. 2005, 127, 17978. (d) Yoshikai, N.;
vated aryl chlorides, heteroaryl chlorides, vinyl chlorides,
and 1,4-dichlorobenzene. In contrast, the pincer nickel
complexes with [5,5]- and [5,6]-fused nickel rings exhib-
ited much lower catalytic activity.
Matsuda, H.; Nakamura, E. J. Am. Chem. Soc. 2009, 131,
9590. (e) Li, G. Y. Angew. Chem. Int. Ed. 2001, 40, 1513.
(f) Ackermann, L.; Gschrei, C. J.; Althammer, A.; Riederer,
M. Chem. Commun. 2006, 1419. (g) Xi, Z.; Liu, B.; Chen,
W. J. Org. Chem. 2008, 73, 3954. (h) Terao, J.; Watanabe,
H.; Ikumi, A.; Kuniyasu, H.; Kambe, N. J. Am. Chem. Soc.
2002, 124, 4222. (i) Terao, J.; Todo, H.; Watanbe, H.; Ikumi,
A.; Kambe, N. Angew. Chem. Int. Ed. 2004, 43, 6180.
(j) Csok, Z.; Vechorkin, O.; Harkins, S. B.; Scopelliti, R.;
Hu, X. J. Am. Chem. Soc. 2008, 130, 8156.
Acknowledgment
We thank the National Basic Research Program of China
(2009CB825300) and the National Natural Science Foundation of
China (20772119) for financial support.
(6) (a) Wang, Z.-X.; Wang, L. Chem. Commun. 2007, 2423.
(b) Sun, K.; Wang, L.; Wang, Z.-X. Organometallics 2008,
27, 5649. (c) Zhang, C.; Wang, Z.-X. Organometallics 2009,
28, 6507. (d) Liu, N.; Wang, Z.-X. J. Org. Chem. 2011, 76,
10031.
Supporting Information for this article is available online at
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(7) Zhang, X.-Q.; Wang, Z.-X. J. Org. Chem. 2012, 77, 3658.
(8) Representative Procedure for the Kumada Reaction
A Schlenk tube was charged with 1 (2.8 mg, 0.005 mmol),
THF (1.5 mL), and 2-chloroanisole (0.0718 g, 0.5 mmol). To
the stirred solution was added dropwise a solution of 4-
MeC6H4MgBr in THF (1.5 mL, 0.5 M in THF) at 30 °C.
Stirring was continued at 30 °C for 24 h. The reaction was
ceased by addition of H2O (10 mL) and several drops of
AcOH. The mixture was extracted with EtOAc (3 × 10 mL)
and the combined organic layers were dried over anhyd
Na2SO4. The Na2SO4 was removed by filtration and washed
with EtOAc. The resulting solution was concentrated by
rotary evaporation, and the residue was purified by
References and Notes
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Catalyzed Cross-Coupling Reactions; de Meijere, A.;
Diederich, F., Eds.; Wiley-VCH: Weinheim, 2nd ed., 2004.
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Organic Synthesis; Tsuji, J., Ed.; John Wiley and Sons:
Chichester, 2000. (d) Cross-Coupling Reactions: A
Practical Guide; Miyaura, N., Ed.; Springer: Berlin, 2002.
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Schmieder-van de Vondervoort, L.; de Vries, A. H. M.; de
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column chromatography on silica gel (eluent: PE) to afford
1-methoxy-2-(p-tolyl)benzene (0.0917 g, 92%) as a white
solid. 1H NMR (300 MHz, CDCl3): δ = 2.38 (s, 3 H, Me),
3.79 (s, 3 H, OMe), 6.95–7.08 (m, 2 H, C6H4), 7.21 (d, J =
7.8 Hz, 2 H, C6H4), 7.26–7.32 (m, 2 H, C6H4), 7.42 (d, J =
8.1 Hz, 2 H, C6H4). 13C NMR (75 MHz, CDCl3): δ = 21.31,
55.66, 111.37, 120.94, 128.48, 128.86, 129.53, 130.92,
135.76, 136.69, 156.67.
(9) 1H NMR (300 MHz, CDCl3): δ = 2.41 (s, 3 H, CH3), 2.72 (s,
3 H, CH3), 7.36 (d, J = 8.1 Hz, 2 H, C6H4), 7.50 (t, J = 7.2
Hz, 1 H, Ar), 7.67–7.71 (m, 2 H, Ar), 7.95 (d, J = 8.4 Hz, 1
H, Ar), 8.05 (d, J = 8.1 Hz, 2 H, C6H4), 8.15 (d, J = 8.4 Hz,
1 H, Ar). 13C NMR (75 MHz, CDCl3): δ = 19.09, 21.44,
119.66, 123.68, 125.90, 127.26, 127.48, 129.33, 129.60,
130.29, 137.08, 139.31, 144.71, 148.23, 157.09.
(f) Sapountzis, I.; Dube, H.; Knochel, P. Adv. Synth. Catal.
2004, 346, 709. (g) Vechorkin, O.; Hu, X. Angew. Chem. Int.
Ed. 2009, 48, 2937.
(10) 1H NMR (300 MHz, CDCl3): δ = 3.01 (s, 12 H, NCH3), 6.84
(d, J = 7.5 Hz, 4 H, C6H4), 7.55 (d, 4 H, J = 8.7 Hz, C6H4),
7.60 (s, 4 H, C6H4). 13C NMR (75 MHz, CDCl3): δ = 40.81,
113.07, 126.66, 127.18, 127.68, 139.04, 150.01. .
(4) (a) Bedford, R. B.; Cazin, C. S. J.; Holder, D. Coord. Chem.
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Chem. Int. Ed. 2002, 41, 4176. (c) Kantchev, E. A. B.;
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(b) Milne, J. E.; Buchwald, S. L. J. Am. Chem. Soc. 2004,
126, 13028. (c) Yoshikai, N.; Mashima, H.; Nakamura, E.
(11) 1H NMR (300 MHz, CDCl3): δ = 1.84 (s, 3 H, CH3), 1.88 (s,
3 H, CH3), 3.79 (s, 3 H, OCH3), 6.21 (s, 1 H, CH), 6.85 (d,
J = 8.7 Hz, 2 H, C6H4), 7.15 (d, J = 8.7 Hz, 2 H, C6H4). 13
NMR (75 MHz, CDCl3): δ = 19.43, 26.94, 55.29, 113.55,
124.61, 129.90, 131.43, 134.05, 157.74. .
C
Synlett 2013, 24, 2081–2084
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