under vacuum and was directly used for the next cycle reaction.
For each cycle reaction, 0.2 mmol of K2CO3 (10% equiv. to the
first reaction cycle) was supplied into the reaction system.
Acknowledgements
We acknowledge the New Teacher Foundation from Education
Ministry of China (200801081035) and Shanxi Natural Science
Foundation for Youths (2009021009). We also thank Dr Lei
Zhang (BASF, Nederland, BV, De Meern) for his good sugges-
tions to this manuscript.
Characterization and analysis
Small-angle powder X-ray powder diffraction was performed on
a Rigaku diffractometer (Cu Ka, 40 kV, 30 mA). N2 physical
adsorption was carried out on Micromeritics ASAP2020 volu-
metric adsorption analyzer (before the measurements, samples
were out gassed at 393 K for 6 h). The Brunauer–Emmett–
Teller (BET) surface area was evaluated from the data in
the relative pressure range of 0.05 to 0.25. The total pore
volume of each sample was estimated from the amount ad-
sorbed at the highest P/P0 (above 0.99). Pore diameters were
determined from the adsorption branch using the Barrett–
Joyner–Halenda (BJH) method. FT-IR spectra were collected
on Thermo-Nicolet-Nexus 470 infrared spectrometer. UV-vis
spectra were recorded on the JASCOV-550 UV-vis spectropho-
tometer. Diffuse-reflectance UV-vis spectra were also recorded
on the CARY300 spectrophotometer (Varian Co.). Pd content
was analyzed by inductively coupled plasma-atomic emission
spectrometry (ICP-AES, AtomScan16, TJA Co.). C and N
content analysis was conducted on a vario EL (Elementar).
X-Ray photoelectron spectroscopy (XPS) was recorded on
Perkin-Elmer 5400 ESCA, and C1s line at 284.9 eV was used
as a reference. TEM micrographs were taken with a JEM-
2000EX transmission electron microscope at 120 kV. Solid-
state NMR spectra were recorded on an Infinityplus 300 MHz
spectrometer: for 13C CP-MAS NMR experiments, 75.4 MHz
resonant frequency, 4 kHz spin rate, 4 s pulse delay, 1.0 ms
contact time, hexamethyl benzene as a reference compound; for
13Si MAS NMR experiments, 79.6 MHz resonant frequency, 4
kHz spin rate, 4.0 s pulse delay, TMS as a reference compound.
GC analysis was conducted on SP-6800A equipped with SE-54
capillary column.
References
1 (a) N. Miyaura, T. Yanagi and A. Suzuki, Synth. Commun., 1981, 11,
513; (b) A. Biffis, M. Zecca and M. Basato, J. Mol. Catal. A: Chem.,
2001, 173, 249; (c) L. Yin and J. Liebscher, Chem. Rev., 2007, 107,
133; (d) Gerd-Jan ten Brink, I. W. C. E. Arends and R. A. Sheldon,
Science, 2000, 287, 1636.
2 (a) H. Doucet, Eur. J. Org. Chem., 2008, 2013; (b) T. Fujihara, S.
Yoshida, J. Terao and Y. Tsuji, Org. Lett., 2009, 11, 2121; (c) E. A. B.
Kantchev, C. J. O’Brien and M. G. Organ, Angew. Chem., Int. Ed.,
2007, 46, 2768; (d) S. S. Stahl, Angew. Chem., Int. Ed., 2004, 43, 3400;
(e) S. Mannam, S. K. Alamsetti and G. Sekara, Adv. Synth. Catal.,
2007, 349, 2253–2258; (f) K. P. Peterson and R. C. Larock, J. Org.
Chem., 1998, 63, 3185; (g) M. Janssen, C. Muller and D. Vogt, Adv.
Synth. Catal., 2009, 351, 313.
3 (a) A. Corma, H. Garc´ıa and A. Primo, J. Catal., 2007, 251, 39;
(b) B. M. Choudary, S. Madhi and N. S. Chowdari, J. Am. Chem.
Soc., 2002, 124, 14127; (c) G. Wei, W. Q. Zhang, F. Wen, Y. Wang and
M. C. Zhang, J. Phys. Chem. C, 2008, 112, 10827; (d) N. Jamwal, M.
Gupta and S. Paul, Green Chem., 2008, 10, 999; (e) H. Q. Yang, L.
Zhang, P. Wang, Q. H. Yang and C. Li, Green Chem., 2009, 11, 257;
(f) N. Erathodiyil, S. Ooi, A. M. Seayad, Y. Han, S. S. Lee and J. Y.
Ying, Chem.–Eur. J., 2008, 14, 3118; (g) B. Karimi, S. Abedi, J. H.
Clark and V. Budarin, Angew. Chem., Int. Ed., 2006, 45, 4776; (h) T.
Mallat and A. Baiker, Chem. Rev., 2004, 104, 3037; (i) H. L. Wu,
Q. H. Zhang and Y. Wang, Adv. Synth. Catal., 2005, 347, 1356; (j) T.
Matsumoto, M. Ueno, N. Wang and S. Kobayashi, Chem.–Asian J.,
2008, 3, 196; (k) J. Shin, J. Bertoia, K. R. Czerwinski and C. Bae,
Green Chem., 2009, 11, 1576, DOI: 10.1039/b913060h.
4 (a) H. Q. Yang, X. J. Han, G. Li and Y. W. Wang, Green Chem.,
2009, 11, 1184; (b) H. Q. Yang, G. Y. Zhang, X. L. Hong and Y. Y.
Zhu, J. Mol. Catal. A: Chem., 2004, 210, 143; (c) C. M. Crudden, M.
Sateesh and R. Lewis, J. Am. Chem. Soc., 2005, 127, 10045; (d) X. M.
Ma, Y. X. Zhou, J. C. Zhang, A. L. Zhu, T. Jiang and B. X. Han,
Green Chem., 2008, 10, 59.
5 N. T. S. Phan, M. V. D. Sluys and C. W. Jones, Adv. Synth. Catal.,
2006, 348, 609.
6 (a) H. Skaff and T. Emrick, Chem. Commun., 2003, 52; (b) T. W. Kim,
R. Ryoo, M. Kruk, K. P. Gierszal, M. Jaroniec, S. Kamiya and O.
Terasaki, J. Phys. Chem. B, 2004, 108, 11480; (c) H. Q. Yang, J. Li,
J. Yang, Z. M. Liu, Q. H. Yang and C. Li, Chem. Commun., 2007,
1086.
7 S. H. Li, Y. J. Lin, J. G. Cao and S. B. Hang, J. Org. Chem., 2007, 72,
4067.
8 (a) L. F. Liu, Y. H. Zhang and B. W. Xin, J. Org. Chem., 2006, 71,
3994; (b) M. Trilla, Roser Pleixats, M. W. C. Man, C. Bied and J. J. E.
Moreau, Adv. Synth. Catal., 2008, 350, 577; (c) J. Z. Zhang, W. Q.
Zhang, Y. Wang and M. C. Zhang, Adv. Synth. Catal., 2008, 350,
2065.
The 1H NMR data for the coupling products
Biphenyl (CDCl3, 300 MHz, ppm): d 7.57 (d, 4 H, J =
9 Hz); 7.41–7.46 (m, 4 H); 7.34 (t, 2 H, J = 7.5 Hz).
4-Biphenylcarbaldehyde (CDCl3, 300 MHz, ppm): d 10.07 (s,
1 H); 7.95 (d, 2 H, J = 7.8 Hz); 7.75 (d, 2 H, J = 7.8 Hz),
7.43–7.66 (m, 5 H). 4-Acetylbiphenyl (CDCl3, 300 MHz, ppm):
d 8.06 (d, 2 H, J = 6 Hz); 7.39–7.68 (m, 7 H); 2.67 (s, 3 H). 4-
Cyanobiphenyl (CDCl3, 300 MHz, ppm): d 7.53–7.64 (m, 4 H);
7.50 (d, 2 H, J = 7.8 Hz); 7.35–7.42 (m, 3 H). 4-Nitrobiphenyl
(CDCl3, 300 MHz, ppm): d 8.29 (d, 2 H, J = 8.7 Hz); 7.73 (d, 2
H, J = 8.7 Hz); 7.45–7.62 (m, 5 H). 4-Methylbiphenyl (CDCl3,
300 MHz, ppm): d 7.52 (d, 2 H, 6 Hz); 7.43 (d, 2 H, 6 Hz); 7.37
(t, 2 H, 6 Hz); 7.27 (d, 1 H, 6 Hz); 7.21 (d, 2 H, 9 Hz); 2.34 (s,
3 H). 4-Methoxybiphenyl (CDCl3, 300 MHz, ppm): d 7.55–7.60
(m, 4 H); 7.45 (t, 2 H, J = 7.5 Hz); 7.33 (m, 1 H); 7.00 (d, 2 H,
J = 9 Hz); 3.88 (s, 3 H). 2-Methoxybiphenyl (CDCl3, 300 MHz,
ppm): d 7.48–7.51 (m, 2 H); 7.19–7.36 (m, 5 H); 6.86–6.98 (m, 2
H); 3.66 (s, 3 H). 2-Methoxybiphenyl (CDCl3, 300 MHz, ppm):
d 7.09–7.24 (m, 9 H); 2.14 (s, 3 H). 4-Trifluoromethylbiphenyl
(CDCl3, 300 MHz, ppm): d 7.67 (s, 4 H), 7.57–7.59 (d, J =
6.9 Hz, 2 H), 7.38–7.48 (m, 3 H). 4-Chlorobiphenyl (CDCl3,
300 MHz, ppm): d 7.53–7.56 (m, 4 H), 7.35–7.50 (m, 5 H).
9 (a) H. Hagiwara, K. H. Ko, T. Hoshi and T. Suzuki, Chem. Commun.,
2007, 2838.
10 (a) J. H. Kim, J. W. Kim, M. Shokouhimehr and Y. S. Lee, J. Org.
Chem., 2005, 70, 6714; (b) B. W. Glasspoole, J. D. Webb and
C. M. Crudden, J. Catal., 2009, 265, 148; (c) P. D. Stevens, J. Fan,
H. M. R. Gardimalla, M. Yen and Y. Gao, Org. Lett., 2005, 7,
2085; (d) M. J. Gronnow, R. Luque, D. J. Macquarrie and J. H.
Clark, Green Chem., 2005, 7, 552; (e) C. Ornelas, J. Ruiz, L. Salmon
and D. Astruc, Adv. Synth. Catal., 2008, 350, 837; (f) H. Hattori,
K. I. Fujita, T. Muraki and A. Sakaba, Tetrahedron Lett., 2007, 48,
6817.
11 (a) Y. H. Ng, S. Ikeda, T. Harada, Y. Morita and M. Matsumura,
Chem. Commun., 2008, 3181; (b) Y. M. A. Yamada, T. Arakawa,
H. Hocke and Y. Uozumi, Angew. Chem., Int. Ed., 2007, 46, 704;
(c) D. D. Caspi, D. C. Ebner, J. T. Bagdanoff and B. M. Stoltz, Adv.
Synth. Catal., 2004, 346, 185; (d) A. Abad, A. Corma and H. Garc´ıa,
450 | Green Chem., 2010, 12, 441–451
This journal is
The Royal Society of Chemistry 2010
©