LETTER
3135. (l) Gois, P. M. R.; Trindade, A. F.; Verros, L. F.;
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(4) Selected recent examples for this reaction: (a) Deshpande,
A. B.; Bajpai, A. R.; Samant, S. D. Appl. Catal. 2001, 209,
229. (b) Hu, X.; Chuah, G. K.; Jaenicke, S. Appl. Catal.
2001, 217, 1. (c) Choudhary, V. R.; Jana, S. K. J. Catal.
2001, 201, 225. (d) Choudhary, V. R.; Jana, S. K.;
Narkhede, V. S. Appl. Catal. 2002, 235, 207. (e) Shrigadi,
N. B.; Shinde, A. B.; Samant, S. D. Appl. Catal. 2003, 252,
23. (f) Bachari, K.; Millet, J. M. M.; Benaichouba, B.;
Cherifi, O.; Figueras, F. J. Catal. 2004, 221, 55.
Hydroarylation of Arenes with Styrenes
1099
2,4-Dimethyl-1-(1-phenylethyl)benzene (1d):1H NMR (300
MHz, CDCl3): d = 7.27–6.95 (m, 8 H), 4.28 (q, J = 7.2 Hz, 1
H), 2.29 (s, 3 H), 2.19 (s, 3 H), 1.59 (d, J = 7.5 Hz, 3 H). 13
NMR (75 MHz, CDCl3): d = 146.6, 141.1, 136.0, 135.6,
C
131.4, 128.4, 127.8, 126.8, 125.9, 40.8, 22.3, 21.0, 19.8. IR
(film): n = 3024, 2966, 2926, 2872, 1601, 1493, 1451, 1374,
1307, 1192, 1028, 822, 762, 747, 700 cm–1. HRMS: m/z
calcd for C16H18: 210.3142; found: 210.3133.
1,2,3,4-Tetrahydro-6-(1-phenylethyl)naphthalene (1e): 1H
NMR (300 MHz, CDCl3): d = 7.24–6.92 (m, 8 H), 4.08 (q,
J = 7.2 Hz, 1 H), 2.72 (s, 4 H), 1.76 (s, 4 H), 1.61 (d, J = 7.5
Hz, 3 H). 13C NMR (75 MHz, CDCl3): d = 146.8, 143.6,
137.1, 134.9, 129.2, 128.4, 128.3, 127.7, 126.0, 124.9, 44.6,
29.6, 29.1, 23.4, 22.1. IR (film): 3025, 2928, 2857, 1735,
1601, 1496, 1451, 1373, 1284, 1028, 910, 829, 766, 699 cm–1.
HRMS: m/z calcd for C22H28: 292.2191; found: 292.2181.
1-Methoxy-4-(1-phenylethyl)benzene (1f): 1H NMR (300
MHz, CDCl3): d = 7.30–7.12 (m, 7 H), 6.82 (d, J = 8.6 Hz, 2
H), 4.10 (q, J = 6.9 Hz, 1 H), 3.77 (s, 3 H), 1.76, (d, J = 7.2
Hz, 3 H).
1,2-Dimethoxy-4-(1-phenylethyl)benzene (1g): 1H NMR
(300 MHz, CDCl3): d = 7.28–7.15 (m, 5 H), 6.79 (s, 2 H),
6.72 (s, 1 H), 4.09 (q, J = 7.5 Hz, 1 H), 3.85 (s, 3 H), 3.82 (s,
3 H), 1.62 (d, J = 7.2 Hz, 3 H). 13C NMR (75 MHz, CDCl3):
d = 148.9, 146.7, 139.1, 128.4, 128.3, 127.65, 127.55, 127.5,
126.1, 119.4, 111.3, 111.2, 55.94, 55.87, 44.4, 22.1. IR
(film): 3440, 3059, 3025, 2964, 2932, 2872, 2833, 1727,
1602, 1591, 1516, 1451, 1416, 1252, 1236, 1143, 1029, 908,
855, 810, 764, 701 cm–1. HRMS: m/z calcd for C16H18O2:
242.1307; found: 242.1295.
(g) Salavati-Niasari, M.; Hasanalian, J.; Najafian, H. J. Mol.
Catal. A: Chem. 2004, 209, 209. (h) Choudhary, V. R.; Jha,
R.; Choudhari, P. A. J. Chem. Sci. 2005, 117, 635.
(i) Choudhary, V. R.; Jha, R.; Narkhede, V. S. J. Mol. Catal.
A: Chem. 2005, 239, 76.
1,5-Dimethoxy-2,4-bis(1-phenylethyl)benzene (1h): 1H
NMR (300 MHz, CDCl3): d = 7.24–7.11 (m, 10 H), 7.00 (s,
1 H), 6.39 (s, 1 H), 4.45 (q, J = 7.2 Hz, 1 H), 3.73 (s, 1 H),
1.53 (d, J = 7.2 Hz, 3 H), 1.51 (d, J = 7.2 Hz, 3 H). 13C NMR
(75 MHz, CDCl3): d = 156.0, 147.1, 132.2, 128.2, 128.1,
127.68, 127.66, 127.0, 126.8, 126.5, 125.6, 96.0, 55.9, 37.4,
21.3. IR (KBr): 3447, 3024, 2961, 2920, 1610, 1583, 1505,
1491, 1464, 1448, 1293, 1205, 1120, 1033, 839, 821, 757,
744, 697 cm–1. HRMS: m/z calcd for C24H26O2: 346.1933;
found: 346.1922.
(5) The catalyst (InCl3/SiO2) was prepared by adding SiO2 (500
mg, 200–300 mesh) to a stirred solution of InCl3×4H2O (1
mmol) in CHCl3 (10 mL) followed by evaporation of the
solvent in vacuo.
(6) (a) Hui, A. L.; Xu, X. L.; Zha, Z. G.; Zhou, C. L.; Wang, Z.
Y. ARKIVOC 2004, (ix), 52. (b) Zhou, C. L.; Jiang, J. Y.;
Zhou, Y. Q.; Xie, Z.; Miao, Q.; Wang, Z. Y. Lett. Org.
Chem. 2005, 2, 61.
2-(1-Phenylethyl)phenol (1i): 1H NMR (300 MHz, CDCl3):
d = 7.32–6.73 (s, 8 H), 4.69 (s, 1 H), 4.37 (q, J = 7.2 Hz, 1
H), 1.63 (d, J = 7.2 Hz, 3 H).
(7) (a) Screttas, G. C.; Micha-Screttas, M. J. Org. Chem. 1978,
43, 1064. (b) Kanagasabapathy, S.; Sudalai, A.; Benicewicz,
B. C. Tetrahedron Lett. 2001, 42, 3791.
4-Methyl-2-(1-phenylethyl)phenol (1j): 1H NMR (300
MHz, CDCl3): d = 7.26–7.19 (m, 5 H), 7.03 (s, 3 H), 6.91 (d,
J = 7.8 Hz, 1 H), 6.65 (d, J = 8.1 Hz, 1 H), 4.33 (q, J = 7.2
Hz, 1 H), 2.29 (s, 3 H), 1.62 (d, J = 7.2 Hz, 3 H).
Phenethyl(p-tolyl)sulfane (1k): 1H NMR (300 MHz,
CDCl3): d = 7.29–7.10 (m, 9 H), 3.13 (t, J = 7.5 Hz, 2 H),
2.90 (t, J = 7.8 Hz, 2 H), 2.33 (s, 3 H).
(8) The catalyst can be recovered by washing the mixture with
petroleum ether, followed by the removal of the solvent.
(9) Typical Procedure for the FC-Arylation of Styrenes
In a typical experiment, InCl3/SiO2 (0.025 mmol, 5 mol%),
styrene (0.5 mmol, 1 equiv), and anisole (0.55 mmol, 1.1
equiv) were mixed. The solution was heated at 80 °C for 2 h,
cooled down, and gently evaporated under vacuo. The
resulting crude mixture was purified by column
2-(1-Phenylethyl)thiophene (1l): 1H NMR (300 MHz,
CDCl3): d = 7.25–7.13 (m, 7 H), 6.57 (d, J = 4.8 Hz, 1 H),
4.22 (q, J = 7.2 Hz, 1 H), 1.63 (d, J = 7.2 Hz, 3 H).
1-Methoxy-4-(1-p-tolylethyl)benzene (2b): 1H NMR (300
MHz, CDCl3): d = 7.31–6.97 (m, 6 H), 6.94–6.76 (m, 2 H),
4.06 (q, J = 7.2 Hz, 1 H), 3.76 (s, 3 H), 2.26 (s, 3 H), 1.59 (d,
J = 7.2 Hz, 3 H).
chromatography on SiO2 (gradient hexane to hexane–
EtOAc = 100:1) to afford 97 mg (91%) of a colorless oily
product.
(10) Spectroscopic Data for Products
1-Methoxy-4-(2-phenylpropan-2-yl)benzene (2c): 1H NMR
(300 MHz, CDCl3): d = 7.26–7.24 (m, 4 H), 7.16–7.13 (m, 3
H), 6.82–6.79 (m, 2 H), 3.78 (s, 3 H), 1.66 (s, 6 H).
1-[1-(4-Methoxyphenyl)-1-phenylethyl]benzene (2d): 1H
NMR (300 MHz, CDCl3): d = 7.28–7.19 (m, 6 H), 7.11–7.10
(m, 3 H), 7.02–6.99 (m, 2 H), 6.79–6.78 (m, 2 H), 3.79 (s, 3
H), 2.16 (s, 6 H).
1-Methyl-4-(1-phenylethyl)benzene (1a): 1H NMR (300
MHz, CDCl3): d = 7.36–7.10 (m, 9 H), 4.11 (q, J = 7.2 Hz, 1
H), 2.30 (s, 4 H), 1.60 (d, J = 7.5 Hz, 3 H).
1,4-Dimethyl-2-(1-phenylethyl)benzene (1b):1H NMR (300
MHz, CDCl3): d = 7.23–6.95 (m, 9 H), 4.29 (q, J = 6.9 Hz, 1
H), 2.32 (s, 3 H), 2.18 (s, 2 H), 1.60 (d, J = 7.2 Hz, 3 H).
1,2-Dimethyl-4-(1-phenylethyl)benzene (1c): 1H NMR (300
MHz, CDCl3): d = 7.20–6.93 (m, 8 H), 4.07 (q, J = 7.2 Hz, 1
H), 2.20 (s, 6 H), 1.60 (d, J = 7.2 Hz, 3 H).
1-[1-(2-Chlorophenyl)ethyl]-4-methoxybenzene (2e): 1H
NMR (300 MHz, CDCl3): d = 7.33 (d, J = 8.4 Hz, 1 H),
7.20–7.11 (m, 5 H), 6.82 (d, J = 8.4 Hz, 2 H), 4.60 (q, J = 7.2
Synlett 2008, No. 7, 1096–1100 © Thieme Stuttgart · New York