7716
C. Wang et al. / Tetrahedron 62 (2006) 7712–7717
1
4.2.2. 1-Methyl-4-[(E)-2-phenylethenyl]benzene (2b). H
NMR (CDCl3, 500 MHz) d 2.29 (3H, s), 7.00–7.45 (11H,
m); MS, m/z 194 (M+).
4.3.3. (E)-2-(4-Fluorophenylethenyl)trimethylsilane (6c).
1H NMR (CDCl3, 500 MHz) d 7.00–7.39 (4H, m), 6.80 (1H,
d, J¼19.5 Hz), 6.35 (1H, d, J¼19.5 Hz), 0.14 (9H, s); MS,
m/z 194 (M+).
1
4.2.3. 1-Bromo-4-[(E)-2-phenylethenyl]benzene (2c). H
NMR (CDCl3, 500 MHz) d 7.07–7.52 (11H, m); MS, m/z
4.3.4. (E)-2-(4-Chlorophenylethenyl)trimethylsilane
(6d). H NMR (CDCl3, 500 MHz) d 7.10–7.34 (4H, m),
1
258 (M+).
6.78 (1H, d, J¼19.7 Hz), 6.42 (1H, d, J¼19.7 Hz), 0.14
(9H, s); MS, m/z 210 (M+).
4.2.4. 1-Methoxyl-4-[(E)-2-phenylethenyl]benzene (2d).
1H NMR (CDCl3, 500 MHz) d 6.90–7.48 (11H, m), 3.86
(3H, s); MS, m/z 210 (M+).
4.3.5. (E)-2-(4-Bromophenylethenyl)trimethylsilane (6e).
1H NMR (CDCl3, 500 MHz) d 7.05–7.46 (4H, m), 6.78 (1H,
d, J¼19.3 Hz), 6.42 (1H, d, J¼19.3 Hz), 0.14 (9H, s); MS,
m/z 254 (M+).
1
4.2.5. 1-Chloro-4-[(E)-2-phenylethenyl]benzene (2g). H
NMR (CDCl3, 500 MHz) d 7.06–7.51 (11H, m); MS, m/z
214 (M+).
Acknowledgements
4.2.6. 1-[(E)-2-(4-Chlorophenyl)ethenyl]-4-methylbenz-
ene (2h). H NMR (CDCl3, 500 MHz) d 6.96–7.48 (10H,
1
The generous financial support of Natural Science Founda-
tion of China (20375036) is gratefully acknowledged.
m), 2.36 (3H, s); MS, m/z 228 (M+).
4.2.7. 1-[(E)-2-(4-Chlorophenyl)ethenyl]-4-bromobenz-
ene (2i). H NMR (CDCl3, 500 MHz) d 7.00–7.51 (10H,
References and notes
1
m); MS, m/z 292 (M+).
1. (a) Pelter, A.; Smith, K.; Brown, H. C. Borane Reagents;
Academic: London, UK, 1988; (b) Seyden-Penne, J. Reductions
by the Alumino- and Borohydrides in Organic Synthesis; VCH:
New York, NY, 1991; (c) Comprehensive Organic Chemistry;
Pergamon: New York, NY, 1979; Vol. 8.
4.2.8. 1-[(E)-2-(4-Chlorophenyl)ethenyl]-4-methoxylbenz-
ene (2j). 1H NMR (CDCl3, 500 MHz) d 6.90–7.48 (10H, m),
3.84 (3H, s); MS, m/z 244 (M+).
2. Miyai, T.; Inoue, K.; Yasuda, M.; Shibata, I.; Baba, A.
Tetrahedron Lett. 1998, 39, 1929–1932.
3. Inoue, K.; Sawada, A.; Shibata, I.; Baba, A. J. Am. Chem. Soc.
2002, 124, 906–907.
4. Ranu, B. C.;Samanta, S. TetrahedronLett. 2002, 43, 7405–7407.
5. Ranu, B. C.; Das, A.; Alakananda, H. Synthesis 2003, 1012–
1014.
6. Xue, Z.; Yang, D. Y.; Wang, C. Y. J. Organomet. Chem. 2006,
691, 247–250.
1
4.2.9. 1-[(E)-2-Phenylethenyl]cyclohexene (2t). H NMR
(CDCl3, 500 MHz) d 1.65–2.26 (8H, m), 5.69 (1H, t,
J¼4.5 Hz), 6.43 (1H, d, J¼16.5 Hz), 6.74 (1H, d,
J¼16.5 Hz), 7.13–7.31 (5H, m); MS, m/z 184 (M+).
4.3. General procedure for the synthesis of (E)-vinyl-
silanes in InCl3–NaBH4 system
InCl3 (1 mmol), dry solvent (5 mL), and NaBH4 (1 mmol)
were mixed at ꢀ15 ꢁC under nitrogen. After the mixture
was stirred for 30 min, alkynylsilanes (1 mmol) were
added by syringe. The cooling bath was removed. The
reaction mixture was warmed to room temperature, stirred
for 2–4 h. Completion of the reaction was monitored by
TLC. In order to destroy the excessive NaBH4 saturated
NH4Cl solution (5 mL) was added to the reaction mixture.
The reaction mixture was stirred for another 10 min and
filtered. The filtrate was extracted with ethyl ether
(10 mLꢂ3). The combined organic layer was dried over
MgSO4 and concentrated in vacuum. Purification by silica
gel column chromatography (200–300 mesh), using petro-
leum ether (60–90 ꢁC) as eluent could afford the corre-
sponding products, which were identified by 1H NMR
and MS.
7. Wang, C. Y.; Pan, Y. J.; Yang, D. Y. J. Organomet. Chem. 2005,
690, 1705–1709.
8. Shibata, I.; Kato, H.; Ishida, T.; Yasuda, M.; Baba, A. Angew.
Chem., Int. Ed. 2004, 43, 711–714.
9. Inoue, K.; Ishida, T.; Shibata, I.; Baba, A. Adv. Synth. Catal.
2002, 344, 283–286.
10. Hayashi, N.; Shibata, I.; Baba, A. Org. Lett. 2004, 6, 4981–
4983.
11. Takami, K.; Yorimitsu, H.; Oshima, K. Org. Lett. 2002, 4,
2993–2995.
12. Takami, K.; Mikami, S.; Yorimitsu, H.; Shinokubo, H.;
Oshima, K. J. Org. Chem. 2003, 68, 6627–6631.
13. Soderquist, J. A.; Santiago, B. Tetrahedron Lett. 1990, 31,
5113–5117.
14. Wrackmeyer, B.; Badshah, A.; Molla, E.; Mottalib, A.
J. Organomet. Chem. 1999, 584, 98–102.
15. Ma, S.; Liu, F.; Negishi, E. Tetrahedron Lett. 1997, 38, 3829–
3832.
16. Andrus, M. B.; Song, C.; Zhang, J. Q. Org. Lett. 2002, 4, 2079–
2082.
17. Katritzky, A. R.; Tymoshenko, D. O.; Belyakov, S. A. J. Org.
Chem. 1999, 64, 3332–3334.
4.3.1. (E)-2-(Phenylethenyl)trimethylsilane (6a). 1H NMR
(CDCl3, 500 MHz) d 7.18–7.43 (5H, m), 6.87 (1H, d,
J¼19.5 Hz), 6.48 (1H, d, J¼19.5 Hz), 0.15 (9H, s); MS,
m/z 176 (M+).
4.3.2. (E)-2-(4-Methylphenylethenyl)trimethylsilane
(6b). H NMR (CDCl3, 500 MHz) d 7.07–7.34 (4H, m),
18. Tewari, R. S.; Kumari, N.; Kendurkar, P. J. Chem. Eng. Data
1976, 21, 125–131.
1
6.81 (1H, d, J¼19.2 Hz), 6.34 (1H, d, J¼19.2 Hz), 2.59
19. Colvin, E. W. Comprehensive Organometallic Chemistry;
Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon:
(3H, s), 0.15 (9H, s); MS, m/z 190 (M+).