Organometallics
Article
(d, J = 3.0 Hz), 128.7, 128.5 (d, J = 3.0 Hz), 128.0 (d, J = 8.0 Hz),
127.7, 127.5, 126.5, 115.6 (d, J = 22.0 Hz).
(E)-1-Methyl-3-styrylbenzene (3n).10b White solid (188 mg, 97%,
E:Z > 99:1). 1H NMR (600 MHz, CDCl3, ppm): 7.50 (d, J = 6.0 Hz,
2H), 7.41 (d, J = 6.0 Hz, 2H), 7.35 (t, J = 6.0 Hz, 2H), 7.26−7.23 (m,
1H), 7.16 (d, J = 6.0 Hz, 2H), 7.11−7.04 (m, 2H), 2.36 (s, 3H). 13C
NMR (100 MHz, CDCl3, ppm): 138.3, 137.5, 137.4, 128.9, 128.8,
128.7, 128.6, 127.6, 127.3, 126.6, 123.8, 21.5.
(E)-1-Chloro-4-styrylbenzene (3c).13 White solid (204 mg, 95%,
E:Z > 99:1). 1H NMR (400 MHz, CDCl3, ppm): 7.50 (d, J = 8.0 Hz,
2H), 7.43 (d, J = 8.0 Hz, 2H), 7.38−7.24 (m, 5H), 7.10−7.01 (m,
2H). 13C NMR (100 MHz, CDCl3, ppm): 137.0, 135.9, 133.2, 129.3,
128.9, 128.8, 127.9, 127.7, 127.4, 126.6.
(E)-1-Methoxy-3-styrylbenzene (3o).18 Colorless liquid (204 mg,
97%, E:Z > 99:1). 1H NMR (400 MHz, CDCl3, ppm): 7.53 (d, J = 8.0
Hz, 2H), 7.37 (t, J = 8.0 Hz, 2H), 7.31−7.27 (m, 2H), 7.53 (d, J = 8.0
Hz, 4H), 6.84 (m, 1H), 3.86 (s, 3H). 13C NMR (100 MHz, CDCl3,
ppm): 160.0, 138.8, 137.3, 129.7, 129.1, 128.7, 128.6, 127.7, 126.6,
119.3, 113.4, 111.8, 55.3.
(E)-1-Bromo-4-styrylbenzene (3d).13 White solid (246 mg, 95%,
E:Z > 99:1). 1H NMR (600 MHz, CDCl3, ppm): 7.52−7.48 (m, 4H),
7.39−7.36 (m, 4H), 7.27 (t, J = 7.2 Hz, 1H), 7.10 (d, J = 16.2 Hz,
1H), 7.04 (d, J = 16.2 Hz, 1H). 13C NMR (100 MHz, CDCl3, ppm):
137.0, 136.3, 131.8, 129.5, 128.8, 128.0, 127.9, 127.4, 126.6, 121.3.
(E)-1-Styryl-4-(trifluoromethyl)benzene (3e).13 White solid (238
mg, 96%, E:Z > 99:1). 1H NMR (400 MHz, CDCl3, ppm): 7.64−7.59
(m, 4H), 7.55 (d, J = 8.0 Hz, 2H), 7.40 (t, J = 8.0 Hz, 2H), 7.32 (t, J
= 8.0 Hz, 1H), 7.21 (d, J = 16.0 Hz, 1H), 7.13 (d, J = 16.0 Hz, 1H).
13C NMR (100 MHz, CDCl3, ppm): 140.8, 136.7, 131.2, 129.4 (q, J =
34.5 Hz), 128.8, 128.3, 127.1, 126.8, 126.6, 125.7 (q, J = 3.7 Hz),
124.2 (q, J = 271.6 Hz).
(E)-1-Chloro-2-styrylbenzene (3p).19 Colorless liquid (208 mg,
97%, E:Z > 99:1). 1H NMR (400 MHz, CDCl3, ppm): 7.71 (d, J = 8.0
Hz, 1H), 7.59−7.53 (m, 3H), 7.40 (t, J = 8.0 Hz, 3H), 7.33−7.27 (m,
2H), 7.21 (t, J = 8.0 Hz, 1H), 7.10 (d, J = 16.0 Hz, 1H). 13C NMR
(100 MHz, CDCl3, ppm): 137.1, 135.5, 133.5, 131.3, 129.9, 128.8,
128.6, 128.1, 127.0, 126.9, 126.5, 124.8.
(E)-1-Bromo-2-styrylbenzene (3q)..19,20 Colorless liquid (246 mg,
95%, E:Z > 99:1). 1H NMR (400 MHz, CDCl3, ppm): 7.79 (d, J = 8.0
Hz, 1H), 7.62−7.49 (m, 4H), 7.41 (t, J = 8.0 Hz, 2H), 7.35−7.30 (m,
2H), 7.14 (t, J = 8.0 Hz, 1H), 7.07 (d, J = 16.0 Hz, 1H). 13C NMR
(100 MHz, CDCl3, ppm): 137.2, 137.1, 133.1, 131.5, 128.9, 128.8,
128.1, 127.6, 127.5, 126.9, 126.8, 124.2.
Ethyl (E)-4-Styrylbenzoate (3f).13 White solid (244 mg, 97%, E:Z
1
> 99:1). H NMR (400 MHz, CDCl3, ppm): 8.04 (d, J = 12.0 Hz,
2H), 7.55 (t, J = 8.0 Hz, 4H), 7.38 (t, J = 8.0 Hz, 2H), 7.30 (t, J = 8.0
Hz, 1H), 7.22 (d, J = 16.0 Hz, 1H), 7.13 (d, J = 16.0 Hz, 1H), 4.39
(q, J = 8.0 Hz, 2H), 1.41 (t, J = 8.0 Hz, 3H). 13C NMR (100 MHz,
CDCl3, ppm): 166.5, 141.8, 136.8, 131.2, 130.0, 129.3, 128.8, 128.2,
127.6, 126.8, 126.3, 61.0, 14.4.
(E)-1-Methoxy-2-styrylbenzene (3r).12 Colorless liquid (200 mg,
95%, E:Z > 99:1). 1H NMR (400 MHz, CDCl3, ppm): 7.65 (d, J = 8.0
Hz, 1H), 7.60−7.54 (m, 3H), 7.40 (t, J = 8.0 Hz, 2H), 7.29 (t, J = 8.0
Hz, 2H), 7.17 (d, J = 16.0 Hz, 1H), 7.02 (t, J = 8.0 Hz, 1H), 6.95 (d, J
= 12.0 Hz, 1H), 3.92 (s, 3H). 13C NMR (100 MHz, CDCl3, ppm):
157.0, 138.0, 129.2, 128.7, 128.7, 127.4, 126.6, 126.5, 126.4, 123.6,
120.8, 111.0, 55.6.
(E)-N,N-Dimethyl-4-styrylaniline (3g).13 White solid (217 mg,
97%, E:Z > 99:1). 1H NMR (400 MHz, CDCl3, ppm): 7.49 (d, J = 8.0
Hz, 2H), 7.43 (d, J = 8.0 Hz, 2H), 7.34 (t, J = 8.0 Hz, 2H), 7.21 (t, J =
8.0 Hz, 1H), 7.06 (d, J = 16.0 Hz, 1H), 6.93 (d, J = 16.0 Hz, 1H),
6.75 (d, J = 12.0 Hz, 2H), 2.99 (s, 6H). 13C NMR (100 MHz, CDCl3,
ppm): 150.0, 138.2, 128.8, 128.6, 127.6, 126.7, 126.1, 124.5, 112.6,
40.6.
(E)-1-Methyl-2-styrylbenzene (3s).13 Colorless liquid (183 mg,
94%, E:Z = 92:8). 1H NMR (400 MHz, CDCl3, ppm): 7.67 (d, J = 8.0
Hz, 1H), 7.60 (d, J = 8.0 Hz, 2H), 7.46−7.39 (m, 3H), 7.36−7.20 (m,
4H), 7.08 (d, J = 16.0 Hz, 1H). 2.51 (s, 3H). 13C NMR (100 MHz,
CDCl3, ppm): 137.8, 136.5, 135.9, 130.5, 130.1, 128.8, 127.7, 126.7,
126.6, 126.4, 125.5, 20.1.
(E)-1-Methyl-4-styrylbenzene (3h).13 White solid (188 mg, 97%,
E:Z > 99:1). 1H NMR (400 MHz, CDCl3, ppm): 7.52 (d, J = 8.0 Hz,
2H), 7.43 (d, J = 8.0 Hz, 2H), 7.36 (t, J = 8.0 Hz, 2H), 7.28−7.24 (m,
1H), 7.18 (d, J = 8.0 Hz, 2H), 7.08−7.10 (m, 2H), 2.38 (s, 3H). 13C
NMR (100 MHz, CDCl3, ppm): 137.6, 134.6, 129.4, 128.7, 128.7,
127.72, 127.4, 126.5, 126.4, 21.3.
(E)-1,2-Bis(4-chlorophenyl)ethane (3t).21 White solid (234 mg,
94%, E:Z > 99:1). 1H NMR (600 MHz, CDCl3, ppm): 7.44−7.41 (m,
4H), 7.34−7.32 (m, 4H), 7.02 (s, 2H). 13C NMR (150 MHz,
CDCl3): 135.6, 133.5, 128.9, 128.0, 127.7.
(E)-1-Methoxy-4-styrylbenzene (3i).13 White solid (204 mg, 97%,
E:Z > 99:1). 1H NMR (400 MHz, CDCl3, ppm): 7.50−7.45 (m, 4H),
7.35 (t, J = 8.0 Hz, 2H), 7.26−7.24 (m, 1H), 7.07 (d, J = 16.0 Hz,
1H), 6.98 (d, J = 16.0 Hz, 1H), 6.91 (d, J = 8.0 Hz, 2H), 3.84 (s, 3H).
13C NMR (100 MHz, CDCl3, ppm): 159.3, 137.7, 130.2, 128.7, 128.2,
127.7, 127.2, 126.6, 126.26, 114.2, 55.4.
(E)-1,2-Bis(4-bromophenyl)ethane (3u).21 White solid (324 mg,
96%, E:Z > 99:1). 1H NMR (600 MHz, CDCl3, ppm): 7.48 (d, J = 8.4
Hz, 4H), 7.37 (d, J = 8.4 Hz, 4H), 7.02 (s, 2H). 13C NMR (150 MHz,
CDCl3): 135.9, 131.9, 128.2, 128.0, 121.7.
(E)-1,2-Bis(4-methoxyphenyl)ethene (3v).21 White solid (223 mg,
93%, E:Z > 99:1). 1H NMR (400 MHz, CDCl3, ppm): 7.43 (d, J = 8.0
Hz, 4H), 6.93 (s, 2H), 6.89 (d, J = 8.0 Hz, 4H), 3.83 (s, 6H). 13C
NMR (100 MHz, CDCl3): 159.0, 130.5, 127.4, 126.2, 114.1, 55.3.
(E)-1-Methoxy-4-(4-(trifluoromethyl)styryl)benzene (3w).22
White solid (264 mg, 95%, E:Z > 99:1). 1H NMR (400 MHz,
CDCl3, ppm): 7.61−7.55 (m, 4H), 7.48 (d, J = 8.0 Hz, 2H), 7.15 (d, J
= 16.0 Hz, 1H), 7.00 (d, J = 16.0 Hz, 1H), 6.93 (d, J = 12.0 Hz, 2H),
3.84 (s, 3H). 13C NMR (100 MHz, CDCl3): 159.8, 141.2, 130.7,
129.4, 128.8 (q, J = 32.5 Hz), 128.1, 126.3, 125.7 (q, J = 3.7 Hz),
125.0, 124.4 (q, J = 272.6 Hz), 114.3, 55.4.
(E)-Trimethyl(4-styrylphenyl)silane (3j).13 White solid (242 mg,
96%, E:Z > 99:1). 1H NMR (400 MHz, CDCl3, ppm): 7.54−7.50 (m,
6H), 7.37 (t, J = 8.0 Hz, 2H), 7.29−7.25 (m, 1H), 7.18−7.09 (m,
2H), 0.29 (s, 9H). 13C NMR (100 MHz, CDCl3, ppm): 141.1, 138.9,
138.5, 134.8, 130.0, 129.8, 128.8, 127.7, 126.9, 0.
(E)-1-Butyl-4-styrylbenzene (3k). White solid (227 mg, 96%, E:Z >
1
99:1). H NMR (400 MHz, CDCl3, ppm): 7.50 (d, J = 8.0 Hz, 2H),
7.43 (d, J = 8.0 Hz, 2H), 7.34 (t, J = 8.0 Hz, 2H), 7.24 (t, J = 8.0 Hz,
1H), 7.17 (d, J = 8.0 Hz, 2H), 7.12−7.03 (m, 2H), 2.61 (t, J = 8.0 Hz,
2H), 1.64−1.57 (m, 2H), 1.41−1.32 (m, 2H), 0.93 (t, J = 8.0 Hz,
3H). 13C NMR (100 MHz, CDCl3, ppm): 142.7, 137.6, 134.8, 128.8,
128.7, 127.8, 127.4, 126.5, 126.4, 35.5, 33.6, 22.4, 14.0. HRMS for
C18H20 + H, 237.1643. Found, 237.1636.
(E)-1-Phenyl-1-enylferrocene (3x).13 Red solid (280 mg, 97%, E:Z
> 99:1). 1H NMR (400 MHz, CDCl3, ppm): 7.45 (d, J = 8.0 Hz, 2H),
7.34 (t, J = 8.0 Hz, 2H), 7.24 (t, J = 8.0 Hz, 1H), 6.89 (d, J = 16.0 Hz,
1H), 6.72 (d, J = 16.0 Hz, 1H), 4.47 (s, 2H), 4.29 (s, 2H), 4.15 (s,
5H). 13C NMR (100 MHz, CDCl3): 137.9, 128.7, 126.9, 126.8, 126.1,
125.8, 83.4, 69.2, 69.1, 66.9.
(E)-1-Chloro-3-styrylbenzene (3l).12 White solid (202 mg, 94%,
E:Z > 99:1). 1H NMR (400 MHz, CDCl3, ppm): 7.52−7.51 (m, 3H),
7.39−7.36 (m, 3H), 7.31−7.22 (m, 3H), 7.12 (d, J = 16.0 Hz, 1H),
7.04 (d, J = 16.0 Hz, 1H). 13C NMR (100 MHz, CDCl3, ppm): 139.3,
136.9, 134.7, 130.2, 129.9, 128.8, 128.1, 127.5, 127.3, 126.7, 126.4,
124.8.
(E)-2-Styrylnaphthalene (3y).13 White solid (216 mg, 94%, E:Z >
1
99:1). H NMR (400 MHz, CDCl3, ppm): 7.89−7.83 (m, 4H), 7.77
(E)-1-Bromo-3-styrylbenzene (3m).12 White solid (249 mg, 96%,
(d, J = 8.0 Hz, 1H), 7.60 (d, J = 8.0 Hz, 2H), 7.59−7.52 (m, 2H),
7.41 (t, J = 8.0 Hz, 2H), 7.34−7.24 (m, 3H). 13C NMR (100 MHz,
CDCl3): 137.4, 134.7, 133.7, 133.1, 129.1, 128.8, 128.8, 128.3, 128.0,
127.7, 126.7, 126.6, 126.4, 125.9, 123.5.
1
E:Z > 99:1). H NMR (400 MHz, CDCl3, ppm): 7.64 (s, 1H), 7.48
(d, J = 8.0 Hz, 2H), 7.40−7.33 (m, 4H), 7.28−7.17 (m, 2H), 7.08 (d,
J = 16.0 Hz, 1H), 6.99 (d, J = 16.0 Hz, 1H). 13C NMR (100 MHz,
CDCl3, ppm): 139.6, 136.8, 130.4, 130.2, 129.3, 128.8, 128.1, 127.1,
126.7, 125.2, 122.9.
(E)-2-Styrylfuran (3z).13 White solid (151 mg, 81%, E:Z = 98:2).
1H NMR (400 MHz, CDCl3, ppm): 7.47 (d, J = 8.0 Hz, 2H), 7.35 (t,
F
Organometallics XXXX, XXX, XXX−XXX