380
C. Desmarets et al. / Tetrahedron 64 (2008) 372e381
3.5.22. 2-Phenylpyridine (Table 3, entry 26)41
Martinelli, J. R.; Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, 4685;
(f) Joshaghani, M.; Faramarzi, E.; Rafiee, E.; Daryanavard, M.; Xiao, J.;
Baillie, C. J. Mol. Catal. A: Chem 2006, 259, 35; (g) Barder, T. E.
J. Am. Chem. Soc. 2006, 128, 898.
1
Colorless oil. H NMR (400 MHz, CDCl3): d 8.70e8.67
(m, 1H), 8.00e7.96 (m, 2H), 7.73e7.68 (m, 2H), 7.50e7.44
(m, 2H), 7.42e7.36 (m, 1H), 7.23e7.16 (m, 1H). 13C NMR
(100 MHz, CDCl3): d 157.4, 149.5, 139.3, 136.5, 128.8,
128.7, 126.7, 122.1, 120.4. EIMS (m/z): 155 (Mþ).
3. (a) El-Sayed, M. A. Acc. Chem. Res. 2001, 34, 257; (b) Crooks, R. M.;
Zhao, M. Q.; Sun, L.; Chechik, V.; Yeung, L. K. Acc. Chem. Res. 2001,
34, 181; (c) Roucoux, A.; Schulz, J.; Patin, H. Chem. Rev. 2002, 102,
3757; (d) Bell, A. T. Science 2003, 299, 1688; (e) Moreno-Manas, E.;
Pleixats, R. Acc. Chem. Res. 2003, 36, 638; (f) Studer, M.; Blaser,
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F.; Aranzaes, J. R. Angew. Chem., Int. Ed. 2005, 44, 7852.
3.5.23. 3-Phenylpyridine (Table 3, entry 27)41
Colorless oil. 1H NMR (400 MHz, CDCl3): d 8.86 (d,
J¼1.8 Hz, 1H), 8.59 (d, J¼1.8 Hz, 1H), 7.87e7.85 (m, 1H),
7.58e7.55 (m, 2H), 7.50e7.37 (m, 4H). 13C NMR
(100 MHz, CDCl3): d 148.3, 148.2, 137.8, 136.7, 134.5,
129.1, 128.1, 127.2, 123.6. EIMS (m/z): 155 (Mþ).
4. (a) Advanced Catalysts and Nanostructured Materials; Moser, W. R., Ed.;
Academic: San Diego, CA, 1996; (b) Chusuei, C. C.; Lai, X.; Luo, K.;
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Isaacs, S. R.; Cutler, E. C.; Park, J.-S.; Lee, T. R.; Shon, Y.-S. Langmuir
2005, 21, 5689.
3.5.24. 2-Chloro-5-phenylpyridine (Table 3, entry 28)42
White solid; mp: 55 ꢀC. 1H NMR (400 MHz, CDCl3):
d 8.62 (d, J¼1.8 Hz, 1H), 7.87e7.81 (dd, J¼8.0 and 2.5 Hz,
1H), 7.58e7.37 (m, 6H). 13C NMR (100 MHz, CDCl3):
d 140.0, 139.6, 133.3, 128.9, 128.8, 128.4, 127.5, 127.0.
EIMS (m/z): 188 (Mþ).
€
6. (a) Jansat, S.; Gomez, M.; Philippot, K.; Muller, G.; Guıu, E.; Claver, C.;
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M.; Pleixats, R.; Sebastian, R. M.; Valleibera, A. New J. Chem. 2006,
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Chem. Commun. 2002, 1132; (b) Narayanan, R.; El-Sayed, M. A. J. Am.
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Nishio, R.; Sugiura, M.; Kobayashi, S. Org. Lett. 2005, 7, 4831; (g)
Houdayer, A.; Schneider, R.; Billaud, D.; Ghanbaja, J.; Lambert, J.
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M.; Gohy, J.-F.; Schubert, U. S. J. Mater. Chem. 2006, 16, 3001; (i)
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P. M.; van Koten, G. Organometallics 2006, 25, 154; (j) Illa, O.; Rodri-
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3.5.25. 5-(1-Naphthyl)pyrimidine (Table 3, entry 29)
White solid; mp: 140e145 ꢀC. 1H NMR (400 MHz,
CDCl3): d 7.95e7.92 (m, 3H), 7.59e7.54 (m, 1H), 7.48e
7.42 (m, 3H), 7.40e7.35 (m, 1H), 7.28e7.21 (m, 2H). 13C
NMR (100 MHz, CDCl3): d 138.8, 134.0, 133.9, 133.2,
128.6, 128.5, 128.3, 128.2, 126.9, 126.4, 126.2, 125.8. EIMS
(m/z): 206 (Mþ).
3.5.26. 3-Phenylthiophene (Table 3, entries 30 and 31)43
Pale yellow solid; mp: 89e90 ꢀC. 1H NMR (400 MHz,
CDCl3): d 7.58 (d, J¼7.2 Hz, 2H), 7.42 (m, 1H), 7.38e7.35
(m, 4H), 7.27 (m, 1H). 13C NMR (100 MHz, CDCl3):
d 139.7, 136.4, 129.3, 128.3, 128.2, 127.5, 121.6. EIMS
(m/z): 160 (Mþ).
´
Lett. 2006, 8, 3605; (b) Lemo, J.; Heuze, K.; Astruc, D. Inorg. Chim. Acta
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9. Dubbaka, S. R.; Zhao, D.; Fei, Z.; Rao Volla, C. M.; Dyson, P. J.; Vogel, P.
Synlett 2006, 3155.
Acknowledgements
10. (a) Martinez, S.; Vallribera, A.; Cotet, C. L.; Popovivi, M.; Martin, L.;
Roig, A.; Moreno-Manas, M.; Molins, E. New J. Chem. 2005, 29, 1342;
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Martin, L.; Martinez, S.; Molins, E.; Moreno-Manas, M.; Petrucci, F.;
Roig, A.; Vallribera, A. Tetrahedron 2007, 63, 2519.
We thank Jaafar Ghanbaja (Service Commun de Microsco-
`
´
pique Electronique a Transmission, Nancy Universite) and Dr.
Abdelaziz Ahajji and Pr. Andre Merlin (LERMAB, UMR
´
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