7388
W. Dan et al. / Tetrahedron 66 (2010) 7384e7388
Chem. 2006, 255, 275; (h) Chakraborti, A.; Shivani, K. J. Org. Chem. 2006, 71,
5785; (i) Firouzabadi, H.; Iranpoor, N.; Farahi, S. J. Mol. Catal. A: Chem. 2008, 289,
61; (j) Ranu, B. C.; Jana, R. Adv. Synth. Catal. 2005, 347, 1811; (k) Bandgar, S. B.;
Bandgar, B. P.; Korbad, B. L.; Sawant, S. S. Tetrahedron Lett. 2007, 48, 1287; (l)
Qiu, R.; Zhang, G.; Ren, X.; Xu, X.; Yang, R.; Luo, S.; Yin, S. J. Organomet. Chem.
2010, 695, 1182.
4.3.1. Se-Phenyl benzoselenoate (5b) (Table 4, entry 2). Yellow solid,
mp 40e41 ꢀC (lit.4a 37e38 ꢀC); 1H NMR (300 MHz, CDCl3):
d
7.43e7.52 (m, 5H), 7.60e7.63 (m, 3H), 7.93e7.96 (m, 2H); 13C NMR
(125 MHz, CDCl3):
138.5, 192.3.
d 125.8, 127.3, 128.9, 129.0, 129.3, 133.8, 136.3,
3. Cao, H.; McNamee, L.; Alper, H. J. Org. Chem. 2008, 73, 3530.
4. (a) Peppe, C.; Castro, L. B. D. Can. J. Chem. 2009, 87, 678; (b) Ranu, B. C.; Mandal,
T. J. Org. Chem. 2004, 69, 5793.
5. (a) Chen, R. E.; Zhang, Y. M. Synth. Commun. 1999, 29, 3699; (b) Chowdhury, S.;
Roy, S. Tetrahedron Lett. 1997, 38, 2149.
6. (a) Wang, X. X.; Zou, X. F.; Du, J. X. J. Chem. Res., Synop. 2006, 64; (b) Patra, P. K.;
Shanmugasundaram, K.; Matoba, M.; Nishide, K.; Kajimoto, T.; Node, M.
Synthesis 2005, 447; (c) Bao, W. L.; Zhang, Y. M. Synth. Commun. 1995, 25, 143.
7. Jia, X. S.; Zhang, Y. M. J. Chem. Res., Synop. 2003, 9, 540.
4.3.2. Se-Phenyl 4-methoxybenzoselenoate (5c) (Table 4, entry 3).
Colorless crystal, mp 59e61 ꢀC (lit.22 61e62 ꢀC); 1H NMR (300 MHz,
CDCl3):
7.59e7.63 (m, 2H), 7.91e7.94 (m, 2H); 13C NMR (125 MHz, CDCl3):
55.5, 114.1, 125.8, 128.8, 129.2, 129.6, 131.3, 136.4, 164.4, 191.2.
d 3.88 (s, 3H), 6.95e6.98 (m, 2H), 7.42e7.44 (m, 3H),
d
8. Wu, H. Y.; Chen, R. E.; Zhang, Y. M. Chin. Chem. Lett. 1999, 10, 899.
9. (a) Lakouraj, M. M.; Movassagh, B.; Fadaei, Z. Monatsh. Chem. 2002, 133, 1085;
(b) Movassagh, B.; Lakouraj, M. M.; Fadaei, Z. J. Chem. Res., Synop. 2001, 22.
10. Tian, F. S.; Zhu, Y. M.; Zhang, S. L.; Wang, Y. L. J. Chem. Res., Synop. 2002, 11, 582.
11. Ajiki, K.; Hirano, M.; Tanaka, K. Org. Lett. 2005, 7, 4193.
12. Kim, S.; Kim, S.; Otsuka, N.; Ryu, I. Angew. Chem., Int. Ed. 2005, 44, 6183.
13. Arisawa, M.; Kubota, T.; Yamaguchi, M. Tetrahedron Lett. 2008, 49, 1975.
14. (a) Keck, G.; Grier, M. C. Synlett 1999, 1657; (b) Boger, D. L.; Mathvink, R. J. J. Org.
Chem. 1992, 57, 1429; (c) Chen, C.; Crich, D.; Papadatos, A. J. Am. Chem. Soc. 1992,
114, 8313; (d) Hiiro, T.; Morita, Y.; Inoue, T.; Kambe, N.; Ogawa, A.; Ryu, I.;
Sonoda, N. J. Am. Chem. Soc. 1990, 112, 455; (e) Kobayashi, S.; Uchiro, H.;
Fujishita, Y.; Shiina, I.; Mukaiyama, T. J. Am. Chem. Soc. 1991, 113, 4247.
15. (a) Balzani, V.; Credi, A.; Raymo, F. M.; Stoddart, J. F. Angew. Chem., Int. Ed.
2000, 39, 3348; (b) Yamada, J.; Akutsu, H.; Nishikawa, H.; Kikuchi, K. Chem.
Rev. 2004, 104, 5057; (c) Woon, K. L.; Aldred, M. P.; Vlachos, P.; Mehl, G. H.;
Stirner, T.; Kelly, S. M.; O’Neill, M. Chem. Mater. 2006, 18, 2311; (d) Cristiano, R.;
Vieira, A. A.; Ely, F.; Gallardo, H. Liq. Cryst. 2006, 33, 381.
4.3.3. Se-Phenyl thiophene-2-carboselenoate (5h) (Table 4, entry 6).
Pale yellow solid, mp 57e59 ꢀC (lit.23 60e61); 1H NMR (CDCl3,
300 MHz)
7.70e7.72 (m, 1H), 7.88e7.90 (m, 1H); 13C NMR (CDCl3, 125 MHz)
125.5, 128.0, 129.1, 129.3, 132.0, 133.6, 136.2, 143.0, 183.5.
d 7.16e7.19 (m,1H), 7.42e7.44 (m, 3H), 7.60e7.63 (m, 2H),
d
Acknowledgements
We thank the National Key Technology R&D Program (No.
2007BAI34B00), the Technology Program of Zhejiang Province (No.
2009C31159) and the Natural Science Foundation of Zhejiang
Province (No. Y4080107) for financial support.
16. (a) Munbunjong, W.; Lee, E. H.; Ngernmaneerat, P.; Kim, S. J.; Singh, G.;
Chavasiri, W.; Jang, D. O. Tetrahedron 2009, 65, 2467; (b) Yamamoto, T.;
Moriura, E.; Sawa, A.; Yoshimatsu, M. Chem. Lett. 2008, 37, 1046; (c) Toyofuku,
M.; Murase, E.; Fujiwara, S. I.; Shin-ike, T.; Kuniyasu, H.; Kambe, N. Org. Lett.
2008, 10, 3957; (d) Wallner, O. A.; Szabo, K. J. J. Org. Chem. 2005, 70, 9215; (e)
Movassagh, B.; Mirshojaei, F. Monatsh. Chem. 2003, 134, 831; (f) Nishiyama, Y.;
Kawamatsu, H.; Funato, S.; Tokunaga, K.; Sonoda, N. J. Org. Chem. 2003, 68,
3599; (g) Nishino, T.; Okada, M.; Kuroki, T.; Watanabe, T.; Nishiyama, Y.;
Sonoda, N. J. Org. Chem. 2002, 67, 8696; (h) Beletskaya, I. P.; Sigeev, A. S.;
Peregudov, A. S.; Petrovskii, P. V. Russ. J. Org. Chem. 2001, 37, 1703; (i) Silveira, C. C.;
Braga, A. L.; Larghi, E. L. Organometallics 1999, 18, 5183.
17. Marin, G.; Braga, A. L.; Rosa, A. S.; Galetto, F. Z.; Burrow, R. A.; Gallardo, H.;
Paixao, M. W. Tetrahedron 2009, 65, 4614 and reference therein.
18. Guo, W. X.; Chen, J. X.; Wu, D. Z.; Ding, J. C.; Chen, F.; Wu, H. Y. Tetrahedron
2009, 65, 5240.
19. Guo, W. X.; Lv, G. S.; Chen, J. X.; Gao, W. X.; Ding, J. C.; Wu, H. Y. Tetrahedron
2010, 66, 2297.
20. (a) Chen, J. X.; Wu, H. Y.; Jin, C.; Zhang, X. X.; Xie, Y. Y.; Su, W. K. Green Chem.
2006, 8, 330; (b) Su, W. K.; Chen, J. X.; Wu, H. Y.; Jin, C. J. Org. Chem. 2007, 72,
4524; (c) Xiao, H. L.; Chen, J. X.; Liu, M. C.; Zhu, D. J.; Ding, J. C.; Wu, H. Y. Chem.
Lett. 2009, 38, 170; (d) Cai, M. T.; Lv, G. S.; Chen, J. X.; Gao, W. X.; Ding, J. C.;
Wu, H. Y. Chem. Lett. 2010, 39, 368.
21. Collings, A. J.; Morgan, K. J. Tetrahedron 1964, 20, 2167.
22. Kato, S.; Kabuto, H.; Ishihara, H.; Murai, T. Synthesis 1985, 520.
23. Back, T. G.; Collins, S.; Kerr, R. G. J. Org. Chem. 1981, 46, 1564.
Supplementary data
Supplementary data associated with this article can be found in
References and notes
1. (a) Evans, D. A.; Dart, M. J.; Duffy, J. L.; Yang, M. G. J. Am. Chem. Soc. 1996, 118,
4322; (b) Paz, M. M.; Corrca, J. F.; Cabcza, M. I.; Sardina, F. J. Tetrahedron Lett.
1996, 37, 9259; (c) Um, P. J.; Drucckhammer, D. G. J. Am. Chem. Soc. 1998, 120,
5605; (d) Agarwal, V. K.; Thomas, A.; Schade, S. Tetrahedron 1997, 53, 16213;
(e) Yang, W. I.; Romo, D. Tetrahedron 1997, 53, 16471; (f) Mizumo, M.; Mur-
amuto, I.; Kawakami, T.; Soike, M.; Aimoto, S.; Hanoda, K.; Inazu, T. Tetrahedron
Lett. 1998, 39, 55; (g) White, J. D.; Kim, T. S.; Nambu, M. J. Am. Chem. Soc. 1997,
119, 103.
2. (a) Bandgar, B. P.; More, P. E.; Kamble, V. T.; Sawant, S. S. Aust. J. Chem. 2008, 61,
1006; (b) Chen, C. T.; Kuo, J. H.; Li, C. H.; Barhate, N. B.; Hon, S. W.; Li, T. W.;
Chao, S. D.; Liu, C. C.; Li, Y. C.; Chang, I. H.; Lin, J. S.; Liu, C. J.; Chou, Y. C. Org. Lett.
2001, 3, 3729; (c) Katritzky, A. R.; Shestopalov, A. A.; Suzuki, K. Synthesis 2004,
1806; (d) Yamada, S. I.; Yokoyama, Y.; Shioiri, T. J. Org. Chem. 1974, 39, 3302; (e)
Kadam, S. T.; Kim, S. S. Synthesis 2008, 3307; (f) Zhang, L.; Luo, Y.; Fan, R. H.;
Wu, J. Green Chem. 2007, 9, 1022; (g) Jeyakumar, K.; Chand, D. K. J. Mol. Catal. A: