256
S. Wu et al. / Tetrahedron 67 (2011) 250e256
134.34, 130.19, 129.93, 129.39, 128.77, 128.29, 128.15, 127.93,
127.76, 126.79.
Acknowledgements
This work was financially supported by National Natural Science
Foundation of China (Nos. 20674063 and 20774074) and Special-
ized Research Fund for the Doctoral Program of Higher Education
(20050736001). We also thank Key Laboratory of Eco-Environ-
ment-Related Polymer Materials (Northwest Normal University),
Ministry of Education, for financial support.
4.4.15. 1-(4-Chlorostyryl)benzene (15c). White solid (0.204 g, 95%);
1H NMR (400 MHz, CDCl3):
d
¼7.51e7.49 (d, J¼8 Hz, 2H), 7.45e7.43
(m, 2H), 7.38e7.27 (m, 5H), 7.07e7.06 (d, J¼4 Hz, 2H); 13C NMR
(100 MHz, CDCl3):
d
¼136.92, 135.79, 133.11, 129.25, 128.80, 128.70,
127.84, 127.62, 127.31, 126.50.
4.4.16. 1-((E)-1-(4-Chlorophenyl)prop-1-en-2-yl)benzene
References and notes
(16c). Pale-yellow solid (0.22 g, 96%); 1H NMR (400 MHz,
CDCl3):
d
¼7.52e7.50 (d, J¼8 Hz, 2H), 7.39e7.28 (m, 7H), 6.77 (s,
1. (a) Heck, R. F.; Nolley, J. P. J. Org. Chem. 1972, 37, 2320e2322; (b) Heck, R. F.
Palladium Reagents in Organic Synthesis; Academic: London, 1985; (c) Be-
letskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009e3066.
1H), 2.26 (s, 3H); 13C NMR (100 MHz, CDCl3):
d¼143.62, 138.14,
136.72, 132.12, 130.38, 128.35, 128.30, 127.35, 126.44, 125.95,
17.47.
€
2. (a) Beller, M.; Fischer, H.; Herrmann, W. A.; Ofele, K.; Brossmer, C. Angew. Chem.
€
1995, 107, 1992e1993; (b) Beller, M.; Fischer, H.; Herrmann, W. A.; Ofele, K.;
Brossmer, C. Angew. Chem., Int. Ed. Engl.1995, 34,1848e1849; (c) Herrmann, W. A.;
€
Brossmer, C.; Ofele, K.; Reisinger, C. P.; Priermeier, T.; Beller, M.; Fischer, H. Angew.
4.4.17. 1-(2-(4-Chlorophenyl)-1-phenylvinyl)benzene (17c). Pale-yellow
Chem., Int. Ed. Engl.1995, 34,1844e1848; (d) Bergbreiter, D. E.; Osburn, P. L.; Liu, Y.
S. J. Am. Chem. Soc. 1999, 121, 9531e9538; (e) Littke, A. F.; Fu, G. C. J. Org. Chem.
1999, 64,10e11; (f) Shaughnessy, K. H.; Kim, P.; Hartwig, J. F. J. Am. Chem. Soc.1999,
121, 2123e2132; (g) Huang, J. K.; Nolan, S. P. J. Am. Chem. Soc. 1999, 121,
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1999, 64, 3804e3805; (i) Lee, H. M.; Nolan, S. P. Org. Lett. 2000, 2, 2053e2055.
solid (0.263 g, 91%); 1H NMR (400 MHz, CDCl3):
d¼7.83e7.81
(d, J¼8 Hz, 1H), 7.63e7.58 (m, 3H), 7.52e7.48 (m, 6H); 13C NMR
(100 MHz, CDCl3):
d¼137.54, 132.38, 130.02, 128.23.
€
3. Herrmann, W. A.; Brossmer, C.; Ofele, K.; Beller, M.; Fischer, H. J. Mol. Catal. A:
4.4.18. (E)-tert-Butyl 3-(4-chlorophenyl)acrylate (18c). Colorless oil
(0.228 g, 96%); 1H NMR (400 MHz, CDCl3):
Chem. 1995, 103, 133e146.
d
¼7.55e7.51 (d,
4. (a) Panziera, N.; Pertici, P.; Barazzone, L.; Caporusso, A. M.; Vitulli, G.; Salvadori,
P.; Borsacchi, S.; Geppi, M.; Veracini, C. A.; Martra, G.; Bertinettti, L. J. Catal.
2007, 246, 351e361; (b) Lin, C. A.; Luo, F. T. Tetrahedron Lett. 2003, 44,
7565e7568.
5. (a) Zhao, F. Y.; Shirai, M.; Ikushima, Y.; Arai, M. J. Mol. Catal. A: Chem. 2002, 180,
211e219; (b) Yoon, H.; Ko, S.; Jang, J. Chem. Commun. 2007, 1468e1470.
J¼16 Hz, 1H), 7.45e7.43 (d, J¼8 Hz, 2H), 7.35e7.33 (d, J¼8 Hz,
2H), 6.36e6.32 (d, J¼16 Hz, 1H), 1.53 (s, 9H); 13C NMR (100 MHz,
CDCl3):
28.16.
d
¼166.02, 142.06, 135.79, 133.14, 129.07, 120.75, 80.69,
€
€
6. Prockl, S. S.; Kleist, W.; Gruber, M. A.; Kohler, K. Angew. Chem., Int. Ed. 2004, 43,
1881e1882.
4.4.19. 1-(4-Nitrostyryl)benzene (19c). Yellow solid (0.209 g, 93%);
1H NMR (400 MHz, CDCl3):
7. (a) Zhang, Z. H.; Wang, Z. Y. J. Org. Chem. 2006, 71, 7485e7487; (b) Zhou, H.;
Zhuo, G. L.; Jiang, X. Z. J. Mol. Catal. A: Chem. 2006, 248, 26e31.
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M.; Sateesh, M.; Lewis, R. J. Am. Chem. Soc. 2005, 127, 10045e10050; (c) Meh-
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(d) Cai, M. Z.; Xu, Q. H.; Jiang, J. W. J. Mol. Catal. A: Chem. 2006, 260, 190e196; (e)
Wan, Y.; Wang, H.; Zhao, Q.; Klingstedt, M.; Terasaki, O.; Zhao, D. J. Am. Chem.
Soc. 2009, 131, 4541e4550.
d¼8.24e8.22 (d, J¼8 Hz, 2H),
7.65e7.63 (d, J¼8 Hz, 2H), 7.57e7.55 (d, J¼8 Hz, 2H), 7.42e7.30
(m, 4H), 7.17e7.13 (d, J¼16 Hz, 1H); 13C NMR (100 MHz, CDCl3):
d
¼146.72, 143.82, 136.13, 133.28, 129.62, 128.87, 126.99, 126.25,
124.13, 123.53.
9. (a) Huang, L.; Wang, Z.; Ang, T. P.; Tan, J.; Wong, P. K. Catal. Lett. 2006,112, 219e225;
(b) Okubo, K.; Shirai, M.; Yokoyama, C. Tetrahedron Lett. 2002, 43, 7115e7118.
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215e222; (b) Djakovitch, L.; Koehler, K. J. Am. Chem. Soc. 2001, 123, 5990e5999.
11. Yin, M. Y.; Yuan, G. L.; Wu, Y. Q.; Huang, M. Y.; Jiang, Y. Y. J. Mol Catal. A: Chem.
1999, 147, 93e98.
4.4.20. 1-((E)-1-(4-Nitrophenyl)prop-1-en-2-yl)benzene
(20c). Yellow solid (0.228 g, 95%); 1H NMR (400 MHz, CDCl3):
d
¼8.25e8.23 (d, J¼8 Hz, 2H), 8.13e8.11 (d, J¼8 Hz, 2H), 7.54e7.50
(m, 4H), 7.39e7.30 (m, 1H), 6.85 (s, 1H), 1.56 (s, 3H); 13C NMR
(100 MHz, CDCl3):
d
¼147.37, 145.48, 145.08, 143.05, 129.57, 128.48,
12. Zhou, D. Q.; He, M.; Zhang, Y. H.; Huang, M. Y.; Jiang, Y. Y. Polym. Adv. Technol.
2003, 14, 287e291.
128.41, 127.83, 126.02, 123.62, 17.82.
13. Xu, Y.; Zhang, L.; Cui, Y. J. Appl. Polym. Sci. 2008, 2996e3000.
14. Xue, L.; Jia, B.; Tang, L.; Ji, X. F.; Huang, M. Y.; Jiang, Y. Y. Polym. Adv. Technol.
2004, 15, 346e349.
15. Jia, B.; Yang, X.; Huang, M. Y.; Jiang, Y. Y. React. Funct. Polym. 2003, 57, 163e168.
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Funct. Polym. 2008, 68, 424e430.
17. Lamblin, M.; Nassar-Hardy, L.; Hierso, J. C.; Fouquet, E.; Felpin, F. X. Adv. Synth.
Catal. 2010, 352, 33e79.
18. Kurahashi, T.; Shinokubo, H.; Osuka, A. Angew. Chem., Int. Ed. 2006, 45,
6336e6338.
4.4.21. 1-(2-(4-Nitrophenyl)-1-phenylvinyl)benzene (21c). Yellow
solid (0.273 g, 91%); 1H NMR (400 MHz, CDCl3):
d
¼7.99e7.97 (d,
J¼8 Hz, 2H), 7.37e7.34 (m, 8H), 7.18e7.12 (m, 4H), 7.00 (s, 1H); 13C
NMR (100 MHz, CDCl3):
d¼142.25, 130.13, 129.98, 129.96, 128.92,
128.43, 128.37, 127.84, 125.72, 123.30.
19. Solabannavar, S. B.; Uday, V. D.; Mane, R. B. Green Chem. 2002, 4, 347e348.
20. Iranpoor, N.; Firouzabadi, H.; Tarassoli, A.; Fereidoonnezhad, M. Tetrahedron
2010, 66, 2415e2421.
21. Uozumi, Y.; Kimura, T. Synlett 2002, 2045e2048.
22. Polshettiwar, V.; Hesemann, P.; Moreau, J. J. E. Tetrahedron 2007, 63,
4.4.22. 1-(4-Nitrostyryl)-4-fluorobenzene
(22c). Yellow
¼8.23e8.21 (d, J¼8 Hz,
solid
(0.233 g, 96%); 1H NMR (400 MHz, CDCl3):
d
2H), 7.63e7.61 (d, J¼8 Hz, 2H), 7.55e7.51 (m, 2H), 7.25e7.21 (d,
J¼16 Hz, 1H), 7.11e7.04 (m, 3H); 13C NMR (100 MHz, CDCl3):
6784e6790.
d
¼164.21, 161.73, 146.77, 143.64, 132.00, 128.58, 126.77, 126.07,
23. Ma, X.; Zhou, Y.; Zhang, J.; Zhu, A.; Jiang, T.; Han, B. Green Chem. 2008, 10,
59e66.
124.15, 116.03.