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D. Chang, W. Bao
LETTER
(3) Ogawa, T.; Hayami, K.; Suzuki, H. Chem. Lett. 1989, 769.
(4) Ranu, B. C.; Chattopadhyay, K.; Banerjee, S. J. Org. Chem.
2006, 71, 423.
(12) All products are known compounds except for (E)-b-tolyl-
seleno-p-methylstyrene, (E)-b-propylseleno-p-methoxy-
styrene, (E)-b-propylseleno-p-chlorostyrene and (E)-b-
heptylselenostyrene.
(5) (a) Marcoux, J. F.; Doye, S.; Buchwald, S. L. J. Am. Chem.
Soc. 1997, 119, 10539. (b) Kiyomori, A.; Marcoux, J. F.;
Buchwald, S. L. Tetrahedron Lett. 1999, 40, 2657.
(c) Klapars, A.; Antilla, J. C.; Huang, X. H.; Buchwald, S. L.
J. Am. Chem. Soc. 2001, 123, 7727. (d) Wolter, M.;
Klapars, A.; Buchwald, S. L. Org. Lett. 2001, 3, 3803.
(e) Kwong, F. Y.; Klapars, A.; Buchwald, S. L. Org. Lett.
2002, 4, 581. (f) Wolter, M.; Nordmann, G.; Job, G. E.;
Buchwald, S. L. Org. Lett. 2002, 4, 973. (g) Hennessy, E.
J.; Buchwald, S. L. Org. Lett. 2002, 4, 269.
(6) (a) Bates, C. G.; Gujadhur, R. K.; Venkataraman, D. Org.
Lett. 2002, 4, 2803. (b) Gujadhur, R.; Venkataraman, D.
Synth. Commun. 2001, 31, 2865. (c) Gujadhur, R.;
Venkataraman, D.; Kintigh, J. T. Tetrahedron Lett. 2001, 42,
4791. (d) Gujadhur, R. K.; Bates, C. G.; Venkataraman, D.
Org. Lett. 2001, 3, 4315.
(7) (a) Ma, D.; Zhang, Y.; Yao, J.; Wu, S.; Tao, F. J. Am. Chem.
Soc. 1998, 120, 12459. (b) Ma, D.; Xia, C. Org. Lett. 2001,
3, 2583. (c) Zhu, W.; Ma, D. Chem. Commun. 2004, 7, 888.
(d) Zhu, W.; Ma, D. J. Org. Chem. 2005, 70, 2696. (e) Xie,
X.; Cai, G.; Ma, D. Org. Lett. 2005, 7, 4693.
(8) (a) For reviews of metal-catalyzed reactions in ILs see:
Wasserscheid, P.; Keim, W. Angew. Chem. Int. Ed. 2000, 39,
3772. (b) Ionic Liquids in Synthesis; Wasserscheid, P.;
Welton, T., Eds.; Wiley-VCH: Weinheim / Germany, 2002.
(9) Wang, Z.-M.; Bao, W.-L.; Jiang, Y. Chem. Commun. 2005,
2849.
(E)-b-Tolylseleno-p-methylstyrene (Table 2, Entry 6).
Mp 35–36 °C; yield 91%. 1H NMR (400 MHz, CDCl3): d =
7.43 (d, 2 H, J = 8.2 Hz), 7.20 (d, 2 H, J = 8.2 Hz), 7.81–7.12
(m, 4 H), 7.07 (d, 1 H, J = 15.6 Hz), 6.79 (d, 1 H, J = 15.6
Hz), 2.34 (s, 3 H), 2.31 (s, 3 H). 13C NMR (100 MHz,
CDCl3): d = 137.42, 137.39, 132.94, 132.84, 130.01, 129.29,
125.88, 118.61, 21.18, 21.11. IR: n = 3019, 2916, 2854,
1635, 1594, 1510, 1487, 1191, 1116, 1070, 1016, 962, 832,
805, 781 cm–1. Anal. Calcd for C16H16Se: C, 66.90; H, 5.61.
Found: C, 66.91; H, 5.61.
(E)-b-Propylseleno-p-methoxystyrene (Table 2, Entry 8).
Viscous oil; yield 65%. 1H NMR (400 MHz, CDCl3): d =
7.23 (d, 2 H, J = 8.8 Hz), 6.83 (d, 2 H, J = 8.8 Hz), 6.86 (d,
1 H, J = 16.0 Hz), 6.71 (d, 1 H, J = 16.0 Hz), 3.80 (s, 3 H),
2.77 (t, 2 H, J = 7.2 Hz), 1.73–1.82 (m, 2 H), 1.02 (t, 3 H,
J = 7.2 Hz). 13C NMR (100 MHz, CDCl3): d = 137.40,
131.94, 128.57, 127.00, 125.57, 119.44, 31.57, 30.30, 29.78,
28.76, 26.17, 22.58, 14.06. IR: n = 3025, 2960, 1604, 1509,
1460, 1301, 1251, 1177, 1034, 947, 834, 776 cm–1. Anal.
Calcd for C12H16OSe: C, 56.47; H, 6.32. Found: C, 56.44; H,
6.32.
(E)-b-Propylseleno-p-chlorostyrene (Table 2, Entry 10).
Viscous oil; yield 68%. 1H NMR (400 MHz, CDCl3): d =
7.26 (d, 2 H, J = 8.2 Hz), 7.21 (d, 2 H, J = 8.2 Hz), 7.03 (d,
1 H, J = 16.4 Hz), 6.67 (d, 1 H, J = 16.4 Hz), 2.80 (t, 2 H,
J = 7.4 Hz), 1.75–1.83 (m, 2 H), 1.04 (t, 3 H, J = 7.4 Hz). 13
NMR (100 MHz, CDCl3): d = 136.84, 132.45, 130.32,
C
(10) Taniguchi, N.; Onami, T. J. Org. Chem. 2004, 69, 915.
(11) Representative Procedure for the Synthesis of (E)-b-
Phenylselenostyrene.
128.58, 126.67, 120.50, 28.28, 23.59, 14.39. IR: n = 3021,
2961, 2928, 2869, 1597, 1570, 1494, 1444, 1376, 1281,
1214, 1028, 943, 730, 690 cm–1. Anal. Calcd for C11H13ClSe:
C, 50.89; H, 5.05. Found: C, 50.84; H, 5.06.
CuI (0.057 g, 0.3 mmol), L-proline (0.069 g, 0.6 mmol), Zn
(0.098 g, 1.5 mmol) and dry [Bmim]BF4 (2.00 mL) were
added to a 10-mL flask. The reaction mixture was stirred and
dried by vacuum heating in an oil bath at 110 °C for 0.5 h.
Diphenyl diselenide (0.234 g, 0.75 mmol) was added to the
stirred mixture, and then (E)-(2-bromovinyl) benzene (0.035
g, 1.65 mmol, 1.1 equiv) was injected into the sealed flask.
The reaction was carried out under a nitrogen atmosphere
and monitored by TLC. After the reaction, the resulting
mixture was cooled to r.t. and extracted with Et2O (3 × 5
mL). The extracts were combined and washed with H2O
(2 × 10 mL), and dried over MgSO4. Evaporation of the
solvent under reduced pressure gave a dark brown oil, which
was further purified by column chromatography (PE), which
gave a viscous oil (0.316 g, 83%).This procedure was
followed for the synthesis of all products listed in Table 2.
(E)-b-Heptylselenostyrene (Table 2, Entry 11).
Viscous oil; yield 71%. 1H NMR (400 MHz, CDCl3): d =
7.30 (d, 4 H, J = 4.0 Hz), 7.19–7.22 (m, 1 H), 7.05 (d, 1 H,
J = 16.4 Hz), 6.73 (d, 1 H, J = 16.4 Hz), 2.82 (t, 2 H, J = 7.6
Hz), 1.72–1.80 (m, 2 H), 1.26–1.45 (m, 8 H), 0.88 (t, 3 H,
J = 6.4 Hz). 13C NMR (100 MHz, CDCl3): d = 137.40,
131.94, 128.57, 127.00, 125.57, 119.44, 31.57, 30.3, 29.78,
28.76, 26.17, 22.58, 14.06. IR: n = 3022, 2956, 2925, 2854,
1652, 1597, 1570, 1494, 1460, 1221, 1182, 942, 729, 690
cm–1. Anal. Calcd for C15H22Se: C, 64.05; H, 7.88. Found: C,
64.01; H, 7.89.
Synlett 2006, No. 11, 1786–1788 © Thieme Stuttgart · New York