References and Notes
<A NAME="RW06306ST-1A">1a</A>
Comasseto JV.
J. Organomet. Chem.
1983,
253:
131
<A NAME="RW06306ST-1B">1b</A>
Comasseto JV.
Petragnani N.
J. Organomet. Chem.
1978,
152:
295
<A NAME="RW06306ST-1C">1c</A>
Comasseto JV.
Ling LW.
Petragnani N.
Stefani HA.
Synthesis
1997,
373
<A NAME="RW06306ST-2A">2a</A>
Zeni G.
Stracke MP.
Nogueira CW.
Braga AL.
Menezes PH.
Stefani HA.
Org. Lett.
2004,
6:
1135
<A NAME="RW06306ST-2B">2b</A>
Comasseto JV.
Brandt CA.
Synthesis
1987,
146
<A NAME="RW06306ST-2C">2c</A>
Silveira CC.
Begnini ML.
Boeck P.
Braga AL.
Synthesis
1997,
221
<A NAME="RW06306ST-2D">2d</A>
Cristau HJ.
Chabaud B.
Labaudiniere R.
Christol H.
J. Org. Chem.
1986,
51:
875
<A NAME="RW06306ST-3">3</A>
Ogawa T.
Hayami K.
Suzuki H.
Chem. Lett.
1989,
769
<A NAME="RW06306ST-4">4</A>
Ranu BC.
Chattopadhyay K.
Banerjee S.
J. Org. Chem.
2006,
71:
423
<A NAME="RW06306ST-5A">5a</A>
Marcoux JF.
Doye S.
Buchwald SL.
J. Am. Chem. Soc.
1997,
119:
10539
<A NAME="RW06306ST-5B">5b</A>
Kiyomori A.
Marcoux JF.
Buchwald SL.
Tetrahedron Lett.
1999,
40:
2657
<A NAME="RW06306ST-5C">5c</A>
Klapars A.
Antilla JC.
Huang XH.
Buchwald SL.
J. Am. Chem. Soc.
2001,
123:
7727
<A NAME="RW06306ST-5D">5d</A>
Wolter M.
Klapars A.
Buchwald SL.
Org. Lett.
2001,
3:
3803
<A NAME="RW06306ST-5E">5e</A>
Kwong FY.
Klapars A.
Buchwald SL.
Org. Lett.
2002,
4:
581
<A NAME="RW06306ST-5F">5f</A>
Wolter M.
Nordmann G.
Job GE.
Buchwald SL.
Org. Lett.
2002,
4:
973
<A NAME="RW06306ST-5G">5g</A>
Hennessy EJ.
Buchwald SL.
Org. Lett.
2002,
4:
269
<A NAME="RW06306ST-6A">6a</A>
Bates CG.
Gujadhur RK.
Venkataraman D.
Org. Lett.
2002,
4:
2803
<A NAME="RW06306ST-6B">6b</A>
Gujadhur R.
Venkataraman D.
Synth. Commun.
2001,
31:
2865
<A NAME="RW06306ST-6C">6c</A>
Gujadhur R.
Venkataraman D.
Kintigh JT.
Tetrahedron Lett.
2001,
42:
4791
<A NAME="RW06306ST-6D">6d</A>
Gujadhur RK.
Bates CG.
Venkataraman D.
Org. Lett.
2001,
3:
4315
<A NAME="RW06306ST-7A">7a</A>
Ma D.
Zhang Y.
Yao J.
Wu S.
Tao F.
J. Am. Chem. Soc.
1998,
120:
12459
<A NAME="RW06306ST-7B">7b</A>
Ma D.
Xia C.
Org. Lett.
2001,
3:
2583
<A NAME="RW06306ST-7C">7c</A>
Zhu W.
Ma D.
Chem. Commun.
2004,
7:
888
<A NAME="RW06306ST-7D">7d</A>
Zhu W.
Ma D.
J. Org. Chem.
2005,
70:
2696
<A NAME="RW06306ST-7E">7e</A>
Xie X.
Cai G.
Ma D.
Org. Lett.
2005,
7:
4693
<A NAME="RW06306ST-8A">8a</A> For reviews of metal-catalyzed reactions in ILs see:
Wasserscheid P.
Keim W.
Angew. Chem. Int. Ed.
2000,
39:
3772
<A NAME="RW06306ST-8B">8b</A>
Ionic Liquids in Synthesis
Wasserscheid P.
Welton T.
Wiley-VCH;
Weinheim / Germany:
2002.
<A NAME="RW06306ST-9">9</A>
Wang Z.-M.
Bao W.-L.
Jiang Y.
Chem. Commun.
2005,
2849
<A NAME="RW06306ST-10">10</A>
Taniguchi N.
Onami T.
J. Org. Chem.
2004,
69:
915
<A NAME="RW06306ST-11">11</A>
Representative Procedure for the Synthesis of (E)-β-Phenylselenostyrene.
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]
.
<A NAME="RW06306ST-12">12</A>
All products are known compounds except for (E)-β-tolyl-seleno-p-methylstyrene, (E)-β-propylseleno-p-methoxy-styrene, (E)-β-propylseleno-p-chlorostyrene and (E)-β-heptylselenostyrene.
(
E
)-β-Tolylseleno-
p
-methylstyrene (Table 2, Entry 6).
Mp 35-36 °C; yield 91%. 1H NMR (400 MHz, CDCl3): δ = 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): δ = 137.42, 137.39, 132.94, 132.84, 130.01, 129.29, 125.88, 118.61, 21.18, 21.11.
IR: ν = 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
)-β-Propylseleno-
p
-methoxystyrene (Table 2, Entry 8).
Viscous oil; yield 65%. 1H NMR (400 MHz, CDCl3): δ = 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): δ = 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: ν = 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
)-β-Propylseleno-
p
-chlorostyrene (Table 2, Entry 10).
Viscous oil; yield 68%. 1H NMR (400 MHz, CDCl3): δ = 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). 13C NMR (100 MHz, CDCl3): δ = 136.84, 132.45, 130.32, 128.58, 126.67, 120.50, 28.28, 23.59, 14.39. IR: ν
= 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.
(
E
)-β-Heptylselenostyrene (Table 2, Entry 11).
Viscous oil; yield 71%. 1H NMR (400 MHz, CDCl3): δ = 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): δ = 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: ν = 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.