T. Hashimoto et al. / Journal of Organometallic Chemistry 696 (2011) 99e105
105
ArH), 6.89 (s, 2H, ArH), 6.95 (d, J ¼ 8.1 Hz, 2H, ArH), 9.83 (brs, 1H,
CO2H); 13C NMR (75 MHz, CDCl3)
20.71, 34.65, 38.50, 55.60,
127.49, 128.16, 128.28, 129.94, 130.65, 132.92, 135.02, 140.67, 141.46,
149.58.
d
110.80, 127.65, 129.05, 129.28, 130.95, 155.07, 178.60.
4.2.5. 1,1-Diphenylethene (8e) [11]
4.1.13. 3,3-Bis(2,5-dimethoxyphenyl)propionic acid (4c) [3q]
Colorless crystals; mp 111e112 ꢀC (EtOH/hexane); 1H NMR
Colorless liquid; 1H NMR (300 MHz, CDCl3)
d 5.46 (s, 2H, vinyl-
H), 7.35e7.30 (m, 10H, ArH); 13C NMR (75 MHz, CDCl3)
d 114.24,
(300 MHz, CDCl3)
5.10 (t, J ¼ 7.8 Hz, 1H, CH), 6.66e6.76 (m, 6H, ArH), 8.96 (brs, 1H,
CO2H); 13C NMR (75 MHz, CDCl3)
35.27 38.19, 55.59, 56.17, 111.32,
d
3.00 (d, J ¼ 7.8 Hz, 2H, CH2), 3.70 (s, 12H, OMe),
127.69, 128.15, 128.26, 141.50, 150.08.
d
4.2.6. 1-(3-Bromo-2,4,6-trimethylphenyl)-1-phenylethene(8g) [11]
Colorless liquid; 1H NMR (300 MHz, CDCl3)
2.07 (s, 3H, Me),
111.96, 115.30, 132.33, 151.53, 153.42, 178.12.
d
2.27 (s, 3H, Me), 2.42 (s, 3H, Me), 5.07 (d, J ¼ 1.5 Hz, 1H, vinyl-H),
4.1.14. Ethyl 3-(2,4,6-trimethylphenyl)propenoate (6) [3q]
5.97 (d, J ¼ 1.5 Hz, 1H, vinyl-H), 7.00 (s, 1H, ArH), 7.30e7.24 (m, H,
Colorless liquid; 1H NMR (300 MHz, CDCl3)
d
1.10 (t, J ¼ 7.0 Hz,
ArH); 13C NMR (75 MHz, CDCl3)
d 19.91, 21.41, 23.94, 114.80, 125.45,
125.81, 127.78, 128.50, 129.61, 134.91, 136.13, 136.82, 138.97, 139.97,
147.07.
Me), 1.34 (t, J ¼ 7.0 Hz, Me), 2.28 (s, Me), 2.33 (s, Me), 4.02 (d,
J ¼ 7.0 Hz, CH2), 4.26 (d, J ¼ 7.0 Hz, CH2), 6.02 (d, J ¼ 16.2 Hz, vinyl-
H), 6.09 (d, J ¼ 11.7 Hz, vinyl-H), 6.82 (s, ArH), 6.89 (s, ArH), 7.01 (d,
J ¼ 11.7 Hz, vinyl-H), 7.81 (d, J ¼ 16.2 Hz, vinyl-H).
References
4.2. General procedure for hydroarylation of phenylacetylene in the
presence of FeCl3 and AgOTf
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and CH2Cl2 (1.0 mL) was stirred for about 15 min at room
temperature. An arene (5.0 mmol), a phenylacetylene (1.0 mmol)
and CH2Cl2 (2.0 mL) were then added into the catalysts mixture and
stirred at 30 ꢀC until the completion of the reaction. The reaction
mixture was dissolved in 20 mL of dichloromethane and passed
through a short path silica gel (2.0 g) column to remove the
insoluble catalysts. The column was washed with dichloromethane.
Collected dichloromethane solution was washed with 5% aqueous
NaHCO3 solution to remove TFA and dried over anhydrous Na2SO4.
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Individual pure compounds were isolated from the reaction
mixture by column chromatography on silica gel.
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4.2.1. 1-Phenyl-1-(2,4,6-trimethylphenyl)ethane (8a) [11]
Colorless liquid; 1H NMR (300 MHz, CDCl3)
d 2.11(s, 6H, Me),
(i) M. Kotani, K. Yamamoto, J. Oyamada, Y. Fujiwara, T. Kitamura, Synthesis (2004)
1466;
2.31 (s, 3H, Me), 5.09 (d, J ¼ 1.2 Hz, 1H, vinyl-H), 5.95 (d, J ¼ 1.2 Hz,
1H, vinyl-H), 6.90 (s, 2H, ArH), 7.27e7.20 (m, 5H, ArH); 13C NMR
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1992;
(75 MHz, CDCl3) d 20.06, 21.02, 114.45, 125.82, 127.51, 128.11, 128.39,
136.08, 136.38, 138.17, 139.55, 146.91.
4.2.2. 1-(Pentamethyphenyl)-1-phenylethene (8b) [11]
White crystals; mp 71.4e72.7 ꢀC; 1H NMR (300 MHz, CDCl3)
d
2.10 (s, 6H, Me), 2.24 (s, 6H, Me), 2.29 (s, 3H, Me), 5.06 (d,
J ¼ 1.2 Hz, 1H, vinyl-H), 5.97 (d, J ¼ 1.5 Hz, 1H, vinyl-H), 7.29e7.23
(m, 5H, ArH); 13C NMR (75 MHz, CDCl3)
16.55, 16.75, 17.83, 114.27,
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d
126.01, 127.41, 128.35, 131.56, 132.33, 133.70, 138.72, 140.03, 148.66.
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4.2.3. 1-Phenyl-(2,3,5,6-tetramethylphenyl)ethene (8c) [11]
White Crystals; mp 67.8e68.9 ꢀC; 1H NMR (300 MHz, CDCl3)
d
1.96 (s, 6H, Me), 2.16 (s, 6H, Me), 4.97 (d, J ¼ 1.5 Hz, 1H, vinyl-H),
5.89 (d, J ¼ 1.5 Hz, 1H, vinyl-H), 6.88 (s, 1H, ArH), 7.19e7.11 (m, 5H,
ArH); 13C NMR (75 MHz, CDCl3)
16.63 20.12, 114.16, 125.94, 127.47,
d
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(2005) 1316.
4.2.4. 1-(2,5-Dimethylphenyl)-1-phenylethene (8d) [11]
Colorless liquid; 1H NMR (300 MHz, CDCl3)
d 2.01 (s, 3H, Me),
2.33 (s, 3H, Me), 5.18 (d, J ¼ 1.2 Hz, 1H, vinyl-H), 5.75 (d, J ¼ 1.2 Hz,
1H, vinyl-H), 7.03 (m, 1H, ArH), 7.06 (m, 2H, ArH), 7.28e7.22 (m, 5H,
[13] F. Bergmann, M. Weizmann, E. Dimant, J. Patai, J. Szmuskowics, J. Am. Chem.
Soc. 70 (1948) 1612.
ArH); 13C NMR (75 MHz, CDCl3)
d 19.57, 20.89, 114.61, 126.48,