4918
Z. Du et al. / Tetrahedron 67 (2011) 4914e4918
d
¼7.66e7.59 (m, 4H), 7.43e7.40 (m, 2H), 6.78e6.74 (m, 2H), 3.86 (s,
756, 686; Anal. Calcd for C12H9Cl (188.04): C 76.40, H 4.81. Found: C
76.12, H 4.87.
2H); 13C NMR (100 MHz, CDCl3):
d
¼147.17, 145.48, 132.47, 128.89,
128.15, 126.53, 119.25, 115.31, 109.35; EI-MS (m/z): 195 [Mþþ1], 194
[Mþ], 178, 169, 152, 76; IR ( /cmꢀ1): 3443, 3361, 2224, 1633, 1593,
n
Acknowledgements
1491, 820; Anal. Calcd for C13H10N2 (194.08): C 80.39, H 5.19. Found:
C 80.07, H 5.23.
Financial support by Natural Science Foundation of China
(20702042), the Key Laboratory of Polymer Materials of Gansu
Province (zd-06-18) and NWNU Young Teachers Research Im-
proving Program (NWNU-LKQN-10-11) is acknowledged.
4.3.10. Biphenyl (j). White solid, mp: 70e71 ꢂC (lit.17 69e70 ꢂC). 1H
NMR (400 MHz, CDCl3):
7.36e7.31 (m, 2H); 13C NMR (100 MHz, CDCl3):
127.22, 127.13; EI-MS (m/z): 154 [Mþ], 76; IR ( /cmꢀ1): 1567, 1473,
728, 692; Anal. Calcd for C12H10 (154.08): C 93.46, H 6.54. Found: C
93.11, H 6.61.
d
¼7.60e7.57 (m, 4H), 7.45e7.41 (m, 4H),
d
¼141.19, 128.72,
n
Supplementary data
The general procedures and spectra of products. Supplementary
data related to this article can be found online at doi:10.1016/
4.3.11. 2-Methoxylbiphenyl (k). Colorless viscous liquid (lit.17 Oil).
1H NMR (400 MHz, CDCl3):
d¼7.53e7.50 (m, 2H), 7.41e7.37 (m, 2H),
7.32e7.28 (m, 3H), 7.03e6.95 (m, 2H), 3.80 (s, 3H); 13C NMR
(100 MHz, CDCl3):
d
¼156.40, 138.49, 130.84, 130.65, 129.50, 128.57,
References and notes
127.93, 126.86, 120.77, 111.16, 55.47; EI-MS (m/z): 185 [Mþþ1], 184
[Mþ], 169, 152, 76; IR ( /cmꢀ1): 1603, 1485, 1249, 1119, 763, 759,
n
1. (a) Suzuki, A. Acc. Chem. Res. 1982, 15, 178e184; (b) Miyaura, N.; Suzuki, A.
Chem. Rev. 1995, 95, 2457e2483; (c) Schwartz, E. B.; Knobler, C. B.; Cram, D. J. J.
Am. Chem. Soc. 1992, 114, 10775e10784; (d) Littke, A. F.; Fu, G. C. Angew. Chem.,
Int. Ed. 2002, 41, 4176e4211; (e) Li, C. Chem. Rev. 2005, 105, 3095e3166.
2. (a) Altenhoff, G.; Goddard, R.; Lehmann, C. W.; Glorius, F. Angew. Chem., Int. Ed.
2003, 42, 3690e3693; (b) Eckhardt, M.; Fu, G. C. J. Am. Chem. Soc. 2003, 125,
13642e13643; (c) Schweizer, S.; Becht, J. M.; DrianLe, C. Adv. Synth. Catal. 2007,
349, 1150e1158; (d) Li, J.; Liu, W. Org. Lett. 2004, 6, 2809e2811.
3. (a) Suzuki, A. J. Organomet. Chem. 1999, 576, 147e168; (b) Willis, M. C.; Powell,
L. H.; Claverie, C. K. Angew. Chem., Int. Ed. 2004, 43, 1249e1251; (c) Mohri, S. I.;
Stefinovic, M.; Snieckus, V. J. Org. Chem. 1997, 62, 7072e7073; (d) Liu, D.; Gao,
W.; Dai, Q.; Zhang, X. Org. Lett. 2005, 7, 4907e4910; (e) Altenhoff, G.; Goddard,
R.; Lehmann, C. W.; Glorius, F. J. Am. Chem. Soc. 2004, 126, 15195e15201; (f) Dai,
M.; Liang, B.; Wang, C.; Chen, J.; Yang, Z. Org. Lett. 2004, 6, 221e224.
4. For selected papers on the ligand-free palladium-catalyzed SuzukieMiyaura
cross-coupling reaction, see: (a) Razler, T. M.; Hsiao, Y.; Qian, F.; Fu, R.; Khan, R.
K.; Doubleday, W. J. Org. Chem. 2009, 74, 1381e1384; (b) Molander, G. A.; Bi-
olatto, B. Org. Lett. 2002, 4, 1867e1870; (c) LeBlond, C. R.; Andrews, A. T.; Sun,
Y.; Sowa, J. R., Jr. Org. Lett. 2001, 3, 1555e1557; (d) Kitamura, Y.; Sakurai, A.;
Udzu, T.; Maegawa, T.; Monguchi, Y.; Sajiki, H. Tetrahedron 2007, 63,
10596e10602; (e) Saha, D.; Chattopadhyay, K.; Ranu, B. C. Tetrahedron Lett.
2009, 50, 1003e1006; (f) Souza, A. L. F.; Silva, A. C.; Antunes, O. A. C. Appl.
Organomet. Chem. 2009, 23, 5e8.
687; Anal. Calcd for C13H12O (184.09): C 84.75, H 6.57. Found: C
85.16, H 6.52.
4.3.12. 4-Aminobiphenyl (l). Yellowish-brown solid, mp: 52e54 ꢂC
(lit.29 53e54 ꢂC). 1H NMR (400 MHz, CDCl3):
d
¼7.54e7.52 (m, 2H),
7.41e7.36 (m, 4H), 7.28e7.21 (m, 1H), 6.74 (d, J¼8.4 Hz, 2H), 3.69 (s,
2H); 13C NMR (100 MHz, CDCl3):
d
¼145.78, 141.07, 131.45, 128.60,
127.94, 126.33, 126.20, 115.31; EI-MS (m/z): 170 [Mþþ1], 169 [Mþ],
152, 77; IR (n
/cmꢀ1): 3423, 3391, 1620, 1483, 1260, 835, 761, 693;
Anal. Calcd for C12H11N (169.09): C 85.17, H 6.55. Found: C 85.54,
H 6.51.
4.3.13. 4-Phenylphenol (m). White solid, mp: 169e170 ꢂC (lit.26
165 ꢂC). 1H NMR (400 MHz, CDCl3):
d
¼7.55e7.52 (m, 2H),
7.49e7.46 (m, 2H), 7.43e7.39 (m, 2H), 7.32e7.28 (m, 1H), 6.92e6.88
(m, 2H), 4.85 (s, 1H); 13C NMR (100 MHz, CDCl3):
d
¼155.02, 140.73,
134.04, 128.70,128.38,126.70,115.62; EI-MS (m/z): 171 [Mþþ1], 170
5. Liu, L.; Zhang, Y.; Xin, B. J. Org. Chem. 2006, 71, 3994e3997.
6. Leadbeater, N. E.; Marco, M. Org. Lett. 2002, 4, 2973e2976.
7. Leadbeater, N. E.; Marco, M. J. Org. Chem. 2003, 68, 888e892.
8. Chalker, J. M.; Wood, C. S. C.; Davis, B. G. J. Am. Chem. Soc. 2009, 131,
16346e16347.
[Mþ], 153, 76; IR ( /cmꢀ1): 3412, 1602, 1485, 1258, 832, 757, 686;
n
Anal. Calcd for C12H10O (170.07): C 84.68, H 5.92. Found: C 84.45,
H 5.99.
9. Miao, G.; Ye, P.; Yu, L.; Baldino, C. M. J. Org. Chem. 2005, 70, 2332e2334.
10. Bai, L.; Wang, J.-X.; Zhang, Y. Green Chem. 2003, 5, 615e617.
11. Jiang, N.; Ragauskas, A. J. Tetrahedron Lett. 2006, 47, 197e200.
12. Nereida, M.; Roser, P.; Alexandr, S.; Mercedes, M. S.; Gregorio, A. Eur. J. Org.
Chem. 2010, 5090e5099.
4.3.14. 4-Phenylbenzoic acid (n). White solid, mp: 228e230 ꢂC
(lit.29 225e226 ꢂC). 1H NMR (400 MHz, DMSO-d6):
d
¼12.98 (s,
1H), 8.02 (d, J¼8.4 Hz, 2H), 7.79 (d, J¼8 Hz, 2H), 7.72 (d, J¼7.6 Hz,
2H), 7.50e7.46 (m, 2H), 7.42e7.38 (m, 1H); 13C NMR (100 MHz,
13. Sudeshna, S.; Dipankar, S.; Piyali, D.; Rima, L.; Amitabha, S. Tetrahedron 2009,
65, 4367e4374.
DMSO-d6):
d
¼167.15, 144.32, 139.02, 129.97, 129.60, 129.09,
128.30, 126.98, 126.83; EI-MS (m/z): 199 [Mþþ1], 198 [Mþ], 181,
14. Chen, J.; Spear, S. K.; Huddleston, J. G.; Rogers, R. D. Green Chem. 2005, 7, 64e82.
15. Han, W.; Liu, C.; Jin, Z. Org. Lett. 2007, 9, 4005e4007.
16. Silva, A. C.; Senra, J. D.; Aguiar, L. C. S.; Simas, A. B. C.; Souza, A. L. F.; Malta, L. F.
B.; Antunes, O. A. C. Tetrahedron Lett. 2010, 51, 3883e3885.
17. Han, W.; Liu, C.; Jin, Z. Adv. Synth. Catal. 2008, 350, 501e508.
18. Silva, A. C.; Souza, A. L. F.; Antunes, O. A. C. J. Organomet. Chem. 2007, 692,
3104e3107.
153, 76; IR (n
/cmꢀ1): 1682, 1606, 1485, 1421, 1294, 939, 862, 750,
696; Anal. Calcd for C13H10O2 (198.07): C 78.77, H 5.09. Found: C
79.11, H 4.91.
4.3.15. 1-Biphenyl-4-yl-ethanone (o). White solid, mp: 122e123
19. Liu, L.; Zhang, Y.; Wang, Y. J. Org. Chem. 2005, 70, 6122e6125.
20. Wang, M.; Wang, L. Chin. J. Chem. 2008, 26, 1683e1688.
21. Tao, L.; Xie, Y.; Deng, C.; Li, J. Chin. J. Chem. 2009, 27, 1365e1373.
22. Pan, C.; Liu, M.; Zhang, L.; Wu, H.; Ding, J.; Cheng, J. Catal. Commun. 2008, 9,
508e510.
ꢂC (lit.17,26 120e121 ꢂC). 1H NMR (400 MHz, CDCl3):
d
¼8.04e8.02
(m, 2H), 7.70e7.67 (m, 2H), 7.64e7.62 (m, 2H), 7.49e7.45 (m,
2H), 7.42e7.38 (m, 1H), 2.64 (s, 3H); 13C NMR (100 MHz, CDCl3):
23. Bandgar, B. P.; Bettigeri, S. V.; Phopase, J. Tetrahedron Lett. 2004, 45, 6959e6962.
24. Yin, L.; Zhang, Z.; Wang, Y. Tetrahedron 2006, 62, 9359e9364.
25. Du, Z.; Zhou, W.; Bai, L.; Wang, F.; Wang, J.-X. Synlett 2011, 369e372.
26. Bai, L.; Wang, J.-X. Adv. Synth. Catal. 2008, 350, 315e320.
27. Zhou, W.-J.; Wang, K.-H.; Wang, J.-X.; Gao, Z.-R. Tetrahedron 2010, 66, 7633e7641.
28. Bernini, R.; Cacchi, S.; Fabrizi, G.; Forte, G.; Petrucci, F.; Prastaro, A.; Niembro, S.;
Shafir, A.; Vallribera, A. Green Chem. 2010, 12, 150e158.
29. Wei, J.-F.; Jiao, J.; Feng, J.-J.; Lv, J.; Zhang, X.-R.; Shi, X.-Y.; Chen, Z.-G. J. Org.
Chem. 2009, 74, 6283e6286.
30. Ogata, Y.; Nakajima, K. Tetrahedron 1964, 20, 2751e2754.
31. Rao, M. L. N.; Jadhav, D. N.; Banerjee, D. Tetrahedron 2008, 64, 5762e5772.
32. Manolikakes, G.; Hernandez, C. M.; Schade, M. A.; Metzger, A.; Knochel, P. J. Org.
Chem. 2008, 73, 8422e8436.
d
¼197.76, 145.77, 139.85, 135.82, 128.93, 128.89, 128.22, 127.26,
127.21, 26.66; EI-MS (m/z): 197 [Mþþ1], 196 [Mþ], 181, 153, 76;
IR (n O
/cmꢀ1): 1678, 1261, 837, 764, 686; Anal. Calcd for C14H12
(196.09): C 85.68, H 6.16. Found: C 85.99, H 6.10.
4.3.16. 4-Chlorobiphenyl (p). White solid, mp: 72e74 ꢂC (lit.31
75e76 ꢂC). 1H NMR (400 MHz, CDCl3):
d
¼7.56e7.49 (m, 4H),
7.45e7.33 (m, 5H); 13C NMR (100 MHz, CDCl3):
d
¼139.97, 139.65,
133.35, 128.89, 128.86, 128.37, 127.57, 126.97; EI-MS (m/z): 190
[Mþþ2], 188 [Mþ], 152, 76; IR (
n
/cmꢀ1): 1651, 1560, 1514, 1473, 831,