8508
Y. Li et al. / Tetrahedron 68 (2012) 8502e8508
Lack, D. E.; Davies-Coleman, M. T. Tetrahedron 2000, 56, 9391e9396; (d) Tomori,
(100 MHz, CDCl3):
128.01, 127.07, 123.45 (aromatic and Py carbons).
d 148.38, 148.25, 137.76, 136.56, 134.25, 128.99,
H.; Fox, J. M.; Buchwald, S. L. J. Org. Chem. 2000, 65, 5334e5341; (e) Capdeville,
R.; Buchdunger, E.; Zimmermann, J.; Matter, A. Nat. Rev. Drug Discov. 2002, 1,
493e502; (f) Rosowsky, A.; Chen, H.; Fu, H.; Queener, S. F. Bioorg. Med. Chem.
2003, 11, 59e67; (g) Long, Y. Q.; Jiang, X. H.; Dayam, R.; Sachez, T.; Shoemaker,
R.; Sei, S.; Neamati, N. J. Med. Chem. 2004, 47, 2561e2573; (h) Kertesz, M.; Choi,
C. H.; Yang, S. Chem. Rev. 2005, 105, 3448e3481; (i) Lightowler, S.; Hird, M.
Chem. Mater. 2005, 17, 5538e5549.
4.4.13. 3,5-Diphenylpyridine (6m).21 White solid, mp 136e138 ꢁC
(lit. mp 137e138 ꢁC); 1H NMR (400 MHz, CDCl3):
d
8.85e8.80,
8.08e8.04, 7.68e7.63, 7.54e7.48, 7.47e7.40 (13H, 5m, aromatic
and Py hydrogens). 13C NMR (100 MHz, CDCl3):
146.98,
3. (a) Trilla, M.; Pleixats, R.; Man, M. W. C.; Bied, C.; Moreau, J. J. E. Adv. Synth.
Catal. 2008, 350, 577e590; (b) Desmarets, C.; Omar-Amrani, R.; Walcarius, A.;
Lambert, J.; Champagne, B.; Fort, Y.; Schneider, R. Tetrahedron 2008, 64,
372e381.
d
137.73, 136.57, 132.86, 129.09, 128.19, 127.23 (aromatic and Py
carbons).
4. (a) Wu, Y. J.; Yang, L. R.; Zhang, J. L.; Wang, M.; Zhao, L.; Song, M. P.; Gong, J. F.
Arkivoc 2004, ix, 111e121; (b) Kostas, I. D.; Andreadaki, F. J.; Kovala-Demertzi,
D.; Prentjas, C.; Demertzis, M. A. Tetrahedron Lett. 2005, 46, 1967e1970; (c)
Zhang, J. L.; Zhao, L.; Song, M. P.; Mak, T. C. W.; Wu, Y. J. J. Organomet. Chem.
2006, 691, 1301e1306; (d) Ma, J.; Cui, X. L.; Zhang, B.; Song, M. P.; Wu, Y. J.
Tetrahedron 2007, 63, 5529e5538.
4.4.14. 4-Phenylbenzonitrile (6n).22 White solid, mp 80e82 ꢁC (lit.
mp 84e88 ꢁC); 1H NMR (400 MHz, CDCl3):
d
7.76e7.66, 7.62e7.57,
7.53e7.40 (9H, 3m, aromatic hydrogens). 13C NMR (100 MHz,
CDCl3): 145.61, 139.10, 132.55, 129.07, 128.62, 127.68, 127.18,
d
5. (a) Zhang, C.; Huang, J.; Trudell, M. L.; Nolan, S. P. J. Org. Chem. 1999, 64,
3804e3805; (b) Gstottmayr, C. W. K.; Bohm, V. P. W.; Herdtweck, E.; Grosche,
M.; Herrmann, W. Angew. Chem., Int. Ed. 2002, 41, 1363e1365; (c) Navarro, O.;
Kelly, R. A., III; Nolan, S. P. J. Am. Chem. Soc. 2003, 125, 16194e16195.
6. (a) Weissman, H.; Milstein, D. Chem. Commun. 1999, 1901e1902; (b) Bedford, R.
B.; Cazin, C. S. J. Chem. Commun. 2001, 1540e1541; (c) Wu, K. M.; Huang, C. A.;
Peng, K. F.; Chen, C. T. Tetrahedron 2005, 61, 9679e9687; (d) Lai, Y. C.; Chen, H.
Y.; Hung, W. C.; Lin, C. C.; Hong, F. E. Tetrahedron 2005, 61, 9484e9489.
7. Grasa, G. A.; Hillier, A. C.; Nolan, S. P. Org. Lett. 2001, 3, 1077e1080.
8. (a) Tao, B.; Boykin, D. W. Tetrahedron Lett. 2003, 44, 7993e7996; (b) Li, J. H.; Liu,
W. J. Org. Lett. 2004, 6, 2809e2811; (c) Li, J. H.; Liu, W. J.; Xie, Y. X. J. Org. Chem.
2005, 70, 5409e5412; (d) Li, J. H.; Liang, Y.; Wang, D. P.; Liu, W. J.; Xie, Y. X.; Yin,
D. L. J. Org. Chem. 2005, 70, 2832e2834; (e) Zhang, L.; Cui, Y. C. Acta Chim. Sinica
2005, 63, 924e928; (f) Yang, Y. F.; Zeng, C. X.; Luo, M. F.; Li, Q. L.; Huang, C. B.
Acta Chim. Sinica 2005, 63, 1469e1473; (g) Yi, H.; Liu, J. B.; Li, Q.; Tang, J. Chin.
Chem. Lett. 2005, 16, 1173e1176; (h) Cui, Y. C.; Zhao, X. W.; Zhang, J. W.; Zhang,
L.; Liu, X. M. Acta Chim. Sinica 2006, 64, 42e46; (i) Xie, Y. X.; Li, J. H.; Yin, D. L.
Chin. J. Org. Chem. 2006, 26, 1155e1163; (j) Yang, Y. F.; Zhuang, M.; Zeng, C. X.;
Huang, C. B.; Luo, M. F. Chin. J. Chem. 2006, 24, 1309e1314.
118.94, 110.82 (aromatic carbons).
4.4.15. 3-(Trifluoromethyl)-biphenyl (6o).23 Yellow oil; 1H NMR
(400 MHz, CDCl3):
7.44e7.38 (8H, 4m, aromatic hydrogens). 13C NMR (100 MHz,
CDCl3): 141.95, 139.72, 130.93, 130.41, 129.21, 128.98, 128.01,
d 7.85 (1H, s), 7.81e7.76, 7.64e7.53, 7.52e7.45,
d
127.17, 125.52, 122.81 (aromatic carbons), 123.91 (q, CF3).
4.4.16. 3-Nitrobiphenyl (6p).3b Yellow solid, mp 57e58 ꢁC (lit. mp
59e60 ꢁC); 1H NMR (400 MHz, CDCl3):
d
8.50e8.44, 8.24e8.19,
7.94e7.89, 7.66e7.58, 7.54e7.41 (9H, 5m, aromatic hydrogens). 13C
NMR (100 MHz, CDCl3): 148.65, 142.81, 138.61, 133.04, 129.69,
d
129.13, 128.51, 127.13, 122.01, 121.92 (aromatic carbons).
9. Mukherjee, A.; Sarkar, A. Tetrahedron Lett. 2005, 46, 15e18.
Acknowledgements
10. Farina, V. Adv. Synth. Catal. 2004, 346, 1553e1582.
_
€
11. Gulcemal, S.; Kani, I.; Yılmaz, F.; C¸ etinkaya, B. Tetrahedron 2010, 66, 5602e5606.
12. Koning, B.; Buter, J.; Hulst, R.; Stroetinga, R.; Kellogg, R. M. Eur. J. Org. Chem.
2000, 15, 2735e2743.
We are grateful to the National Natural Science Foundation of
China (No. 21172200) for financial support to this research.
13. Ley, S. V.; Ramarao, C.; Gordon, R. S.; Holmes, A. B.; Morrison, A. J.; McConvey, I.
F.; Shirley, I. M.; Smith, S. C.; Smith, M. D. Chem. Commun. 2002, 1134e1135.
14. Uozumi, Y.; Nakai, Y. Org. Lett. 2002, 4, 2997e3000.
15. Phan, N. T. S.; Browna, D. H.; Styring, P. Tetrahedron Lett. 2004, 45,
7915e7919.
16. Stevens, P. D.; Li, G. F.; Fan, J. D.; Yen, M.; Gao, Y. Chem. Commun. 2005,
4435e4437.
17. Old, D. W.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9722e9723.
18. Han, W.; Liu, C.; Jin, Z. L. Org. Lett. 2007, 9, 4005e4007.
19. Tu, T.; Feng, X. K.; Wang, Z. X.; Liu, X. Y. Dalton Trans. 2010, 39,
10598e10600.
20. Ackermann, L.; Potukuchi, H. K.; Althammer, A.; Born, R.; Mayer, P. Org. Lett.
2010, 12, 1004e1007.
21. Chuang, T. H.; Chen, Y. C.; Pola, S. J. Org. Chem. 2010, 75, 6625e6630.
22. Grossman, O.; Gelman, D. Org. Lett. 2006, 8, 1189e1191.
23. Kasper, W. L.; Morten, M. Eur. J. Org. Chem. 2008, 5244e5253.
References and notes
1. (a) Miyaura, N.; Suzuki., A. Chem. Rev. 1995, 95, 2457e2483; (b) Suzuki, A. J.
Organomet. Chem. 1999, 576, 147e168; (c) Wolfe, J. P.; Singer, R. A.; Yang, B. H.;
Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 9550e9561; (d) Hassan, J.; Sevignon,
M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359e1470; (e)
Corbet, J. P.; Mignani, G. Chem. Rev. 2006, 106, 2651e2710; (f) Phan, N. T. S.; Van
Der Sluys, M.; Jones, C. W. Adv. Synth. Catal. 2006, 348, 609e679; (g) Yin, L.;
Liebscher, J. Chem. Rev. 2007, 107, 133e173; (h) Molander, G. A.; Ellis, N. Acc.
Chem. Res. 2007, 40, 275e286; (i) Martin, R.; Buchwald, S. L. Acc. Chem. Res.
2008, 41, 1461e1473; (j) Alonso, F.; Beletskaya, I. P.; Yus, M. Tetrahedron 2008,
64, 3047e3101.
2. (a) Markham, A.; Goa, K. L. Drugs 1997, 54, 299e311; (b) Gangjee, A.; Devraj, R.;
Queener, S. F. J. Med. Chem. 1997, 40, 470e478; (c) McPhail, K. L.; Rivett, D. E. A.;