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J. Gong et al. / Journal of Organometallic Chemistry 690 (2005) 3963–3969
2.54 (m, 3H, PCy3), 4.21 (s, 5H, C5H5), 4.41 (m, 2H,
C5H3), 4.53 (m, 1H, C5H3), 4.81 (m, 1H, CHMe2),
8.09 (m, 1H, N@CH). 31P{1H} NMR (CDCl3): d
45.57, 46.92. HRMS (positive ESI) calc. for
C32H49ClFeNPPd: 675.1675, found: 675.1670.
3.4. Structure determination
Crystals of 5 were obtained by recrystallization from
CH2Cl2–petroleum ether solution at 0 ꢀC. A single crys-
tal suitable for X-ray analysis was mounted on a glass
fiber. All measurements were made on a Rigaku-IV
imaging plate area detector with graphite monochro-
3.3. General procedure for the coupling reactions
˚
mated Mo Ka radiation (k = 0.71073 A). The data
A Schlenk tube was charged with the appropriate aryl
chloride (1.0 mmol), phenyl boronic acid (0.183 g,
1.5 mmol) and base (2.0 mmol) under nitrogen. The
were corrected for Lorentz and polarization factors.
The structure was solved by direct methods [20] and
expanded using Fourier techniques and refined by full-
matrix least-squares methods. The non-hydrogen atoms
were refined anisotropically, and the hydrogen atoms
were included but not refined. All calculations were per-
formed using the TEXSAN [21] crystallographic software
package of Molecular Structure corporation.
catalyst was introduced as
a
dioxane solution
(0.001 mmol/mL) via syringe, and additional dioxane
was added to obtain a total volume of 6 mL. The reac-
tion mixture was then placed in an oil bath and heated
at 60–100 ꢀC for a certain time, cooled and quenched
with water. The organic layer was separated and the
aqueous layer was extracted with dichloromethane, then
the combined organic layers were washed with water,
dried over MgSO4, filtered, and the solvent was removed
on a rotary evaporator. The residue was analyzed by GC
(dissolved in dioxane, undecane as internal standard) or
purified by column chromatography on silica gel (the
purified products were identified by comparison of melt-
ing points with the literature values [19] or by 1H NMR
spectra).
4. Supplementary material
Crystallographic data for the structural analysis have
been deposited with the Cambridge Crystallographic
Data Centre, CCDC No. 262129. Copies of this informa-
tion may be obtained free of charge from The Director,
CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK,
fax: +44 1223 336 033, e-mail: deposit@ccdc.cam.ac.uk
2,6-Dimethylbiphenyl. Colorless oil. 1H NMR
(CDCl3): d 2.02 (s, 3H, CH3), 2.03 (s, 3H, CH3), 7.12
(m, 5H, Ar-H), 7.32 (m, 1H, Ar-H), 7.39 (m, 2H, Ar-H).
2-Methoxybiphenyl. Colorless oil. 1H NMR (CDCl3):
d 3.81 (s, 3H, OCH3), 6.98 (m, 1H, Ar-H), 7.03(t,
J = 7.6 Hz, 1H, Ar-H), 7.32 (m, 3H, Ar-H), 7.40 (t,
J = 7.6 Hz, 2H, Ar-H), 7.52 (d, J = 7.2 Hz, 2H, Ar-H).
Acknowledgments
We are grateful to the National Natural Science
Foundation of China (Project 20472074) and Education
Ministry of China for their financial support. We thank
Dr. Jared Cumming and Dr. Yusheng Wu for comments
on this paper.
1
2-Phenylpyridine. Colorless oil. H NMR (CDCl3): d
7.24 (m, 1H, Py-H), 7.46 (m, 3H, Ar-H), 7.74 (m, 2H,
Py-H), 8.00 (d, J = 7.2 Hz, 2H, Ar-H), 8.70 (d,
J = 4.4 Hz, 1H, Py-H).
1
3-Phenylpyridine. Colorless oil. H NMR (CDCl3): d
7.45 (m, 4H, Py-H, Ar-H), 7.59 (d, J = 7.4 Hz, 2H, Ar-
H), 7.90 (d, J = 7.8 Hz, 1H, Py-H), 8.60 (s, 1H, Py-H),
8.86 (s, 1H, Py-H).
References
[1] (a) J. Tsuji, Palladium Reagents and Catalysts, Wiley, Chichester,
1995;
2-Methylbiphenyl. Colorless oil. 1H NMR (CDCl3): d
2.27 (s, 3H, CH3), 7.25 (m, 4H, Ar-H), 7.33 (m, 3H, Ar-
H), 7.40 (m, 2H, Ar-H).
(b) F. Diederich, P.J. Stang (Eds.), Metal-Catalyzed Cross-
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4-Methoxybiphenyl. White solid; m.p. 88–90 ꢀC (lit.
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4-Methylbiphenyl. White solid; m.p. 47–49 ꢀC (lit. 48–
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