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CDCl3) δ 7.26–7.19 (m, 10H), 6.60 (s, 2H); 13C NMR
3H); 13C NMR (151 MHz, CDCl3) δ 157.26, 137.39, 130.33,
130.19, 128.94, 128.69, 128.13, 127.01, 126.27, 125.88, 120.30,
110.72, 55.55 ppm.
(151 MHz, CDCl3)
127.47 ppm.
δ
137.62, 130.63, 129.26, 128.60,
(Z)-4-styrylaniline (2b): light yellow oil. Isolated yield when
obtained from 1b under conventional conditions: 93%
(544 mg). Isolated yield under MW/US irradiation: 95%
(Z)-1-methyl-2-styrylbenzene (2i): colourless oil. Isolated yield
under conventional conditions: 94% (550 mg). Isolated yield
1
under MW/US irradiation: 95% (555 mg). H NMR (600 MHz,
1
(556 mg). H NMR (600 MHz, CDCl3) δ 7.30 (d, J=7.5 Hz,
CDCl3) δ 7.26–7.10 (m, 8H), 7.06 (t, J=7.4 Hz, 1H), 6.65 (q,
J=12.2 Hz, 2H), 2.29 (s, 3H) ppm; 13C NMR (151 MHz,
CDCl3) δ 137.21, 137.12, 136.21, 130.60, 130.17, 129.64,
129.03, 129.01, 128.98, 128.96, 128.95, 128.19, 127.33, 127.14,
125.81, 20.00 ppm.
2H), 7.23 (t, J=7.5 Hz, 2H), 7.18 (d, J=7.3 Hz, 1H), 7.07 (d,
J=8.5 Hz, 2H), 6.55 (d, J=8.4 Hz, 2H), 6.46 (d, J=14.1 Hz,
2H) ppm; 13C NMR (151 MHz, CDCl3) δ 138.03, 130.24,
130.18, 128.89, 128.25, 127.84, 127.74, 127.73, 126.78,
114.85 ppm.
(Z)-1-chloro-3-styrylbenzene (2j): colourless oil. Isolated yield
(Z)-1-methyl-4-styrylbenzene (2c): colourless oil. Isolated yield
under conventional conditions: 89% (574 mg). Isolated yield
under MW/US irradiation: 90% (580 mg). H NMR (600 MHz,
CDCl3) δ 7.24–7.22 (m, 6H), 7.16–7.11 (m, 3H), 6.65 (d, J=
12.2 Hz, 1H), 6.52 (d, J=12.2 Hz, 1H) ppm; 13C NMR
(151 MHz, CDCl3) δ 139.20, 136.71, 134.15, 131.66, 129.53,
128.93, 128.91, 128.81, 128.42, 127.54, 127.23, 127.10 ppm.
1
under conventional conditions: 94% (550 mg). Isolated yield
1
under MW/US irradiation: 94% (550 mg). H NMR (600 MHz,
CDCl3) δ 7.30–7.26 (m, 2H), 7.24 (ddd, J=7.4, 6.2, 1.4 Hz,
2H), 7.20 (dd, J=5.1, 3.6 Hz, 1H), 7.19–7.15 (m, 2H), 7.04 (d,
J=7.9 Hz, 2H), 6.59–6.55 (dd, 2H), 2.32 (s, 3H) ppm; 13C
NMR (151 MHz, CDCl3) δ 137.59, 136.97, 134.36, 130.30,
129.65, 129.01, 128.95, 128.89, 128.29, 127.07, 21.35 ppm.
(Z)-1-(3-methoxystyryl)benzene (2k): colourless oil. Isolated
yield under conventional conditions: 86% (542 mg). Isolated
yield under MW/US irradiation: 88% (554 mg). 1H NMR
(600 MHz, CDCl3) δ 7.31–7.22 (m, 4H), 7.20 (d, J=7.1 Hz,
1H), 7.15 (t, J=7.9 Hz, 1H), 6.85 (d, J=7.6 Hz, 1H), 6.82–
6.78 (m, 1H), 6.78–6.73 (m, 1H), 6.60 (q, J=12.2 Hz, 2H),
3.65 (s, 3H) ppm; 13C NMR (151 MHz, ) δ 159.44, 138.63,
137.36, 130.58, 130.24, 129.32, 129.01, 128.30, 127.24, 121.61,
113.81, 113.41, 55.09 ppm.
(Z)-1-(4-methoxystyryl)benzene (2d): yellow oil. Isolated yield
under conventional conditions: 91% (573 mg). Isolated yield
1
under MW/US irradiation: 92% (589 mg). H NMR (600 MHz,
CDCl3) δ 7.29–7.20 (m, 7H), 6.77–6.79 (m, 2H), 6.54 (d, 2H),
3.80 (s, 3H) ppm; 13C NMR (151 MHz, CDCl3) δ 158.76,
137.71, 130.25, 129.86, 128.91, 128.85, 128.33, 127.00, 113.67,
55.28 ppm.
(Z)-1-(4-styrylphenyl)ethanone (2e): yellow oil. Isolated yield
(Z)-1,3-dimethyl-2-styrylbenzene (2l): colourless oil. Isolated
yield under conventional conditions: 82% (511 mg). Isolated
yield under MW/US irradiation: 85% (530 mg). 1H NMR
(600 MHz, CDCl3) δ 7.13 (dt, J=10.1, 4.6 Hz, 4H), 7.04 (d,
J=7.5 Hz, 2H), 7.02–6.96 (m, 2H), 6.66 (d, J=12.3 Hz, 1H),
6.54 (d, J=12.3 Hz, 1H), 2.16 (s, 6H) ppm; 13C NMR
(151 MHz, CDCl3) δ 137.55, 137.17, 135.70, 131.13, 128.88,
128.31, 128.15, 127.57, 127.24, 126.96, 20.31 ppm.
under conventional conditions: 90% (600 mg). Isolated yield
1
under MW/US irradiation: 93% (620 mg). H NMR (600 MHz,
CDCl3) δ 7.80 (d, J=8.3 Hz, 2H), 7.32 (d, J=8.1 Hz, 2H),
7.23 (dd, J=11.8, 6.6 Hz, 5H), 6.72 (d, J=12.2 Hz, 1H), 6.60
(d, J=12.2 Hz, 1H), 2.56 (s, 3H) ppm; 13C NMR (151 MHz,
CDCl3) δ 197.61, 142.39, 136.76, 135.70, 132.52, 129.20,
129.14, 128.93, 128.46, 128.41, 127.64, 26.64 ppm.
(Z)-1-fluoro-2-styrylbenzene (2f): colourless oil. Isolated yield
(Z)-4-styrylpyridine (2m): colourless oil. Isolated yield under
conventional conditions: 62% (336 mg). Isolated yield under
MW/US irradiation: 64% (347 mg). 1H NMR (400 MHz,
CDCl3) δ 8.47 (d, J=6.1 Hz, 2H), 7.25 (ddd, J=14.9, 6.2,
2.6 Hz, 5H), 7.12 (d, J=6.0 Hz, 2H), 6.81 (d, J=12.3 Hz, 1H),
6.52 (d, J=12.3 Hz, 1H) ppm; 13C NMR (101 MHz, CDCl3) δ
149.86, 144.97, 136.15, 134.04, 128.75, 128.46, 127.85, 127.55,
123.50 ppm.
under conventional conditions: 77% (457 mg). Isolated yield
1
under MW/US irradiation: 82% (487 mg). H NMR (400 MHz,
CDCl3) δ 7.26–7.15 (m, 7H), 7.04 (ddd, J=10.0, 8.8, 1.2 Hz,
1H), 6.97–6.89 (m, 1H), 6.72 (d, J=12.2 Hz, 1H), 6.62 (d, J=
12.2 Hz, 1H) ppm. 13C NMR (101 MHz, CDCl3) δ 161.61,
132.24, 132.23, 130.53, 130.50, 128.98, 128.90, 128.75, 128.25,
127.39, 123.64, 123.60, 122.63, 122.60, 115.72 ppm.
(Z)-1-chloro-2-styrylbenzene (2g): Colourless oil. Isolated yield
(Z)-2-styrylpyridine (2n): colourless oil. Isolated yield under
conventional conditions: 53% (288 mg). Isolated yield under
MW/US irradiation: 71% (385 mg). 1H NMR (400 MHz,
CDCl3) δ 8.65–8.51 (m, 1H), 7.42 (td, J=7.7, 1.8 Hz, 1H),
7.28–7.21 (m, 5H), 7.15 (d, J=7.9 Hz, 1H), 7.07 (ddd, J=7.4,
4.8, 0.8 Hz, 1H), 6.83 (d, J=12.5 Hz, 1H), 6.69 (d, J=12.4 Hz,
1H) ppm; 13C NMR (101 MHz, CDCl3) δ 156.35, 149.55,
136.65, 135.61, 133.24, 130.51, 128.87, 128.29, 127.58, 123.84,
121.74. ppm.
under conventional conditions: 84% (539 mg). Isolated yield
1
under MW/US irradiation: 85% (545 mg). H NMR (400 MHz,
CDCl3) δ 7.40 (dd, J=8.0, 1.1 Hz, 1H), 7.24–7.11 (m, 7H),
7.04 (td, J=7.5, 1.1 Hz, 1H), 6.72 (d, J=12.2 Hz, 1H), 6.67 (d,
J=12.2 Hz, 1H) ppm. 13C NMR (101 MHz, CDCl3) δ 136.48,
136.07, 133.72, 131.75, 130.78, 129.55, 129.01, 128.53, 128.22,
127.39, 127.28, 126.39 ppm.
(Z)-1-(2-methoxystyryl)benzene (2h): colourless liquid. Iso-
lated yield under conventional conditions: 92% (580 mg).
Isolated yield under MW/US irradiation: 92% (580 mg). 1H
NMR (600 MHz, CDCl3) δ 7.20 (dddd, J=13.7, 8.5, 6.0,
4.7 Hz, 7H), 6.89 (d, J=8.2 Hz, 1H), 6.76 (t, J=7.5 Hz, 1H),
6.69 (d, J=12.3 Hz, 1H), 6.63 (d, J=12.3 Hz, 1H), 3.83 (s,
(Z)-3-styrylpyridine (2o): light yellow oil. Isolated yield under
conventional conditions: 87% (472 mg). Isolated yield under
MW/US irradiation: 90% (489 mg). 1H NMR (400 MHz,
CDCl3) δ 8.48 (d, J=1.9 Hz, 1H), 8.42 (dd, J=4.8, 1.4 Hz,
1H), 7.51 (dt, J=7.9, 1.6 Hz, 1H), 7.31–7.17 (m, 5H), 7.12 (dd,
Adv. Synth. Catal. 2021, 363, 1–12
9
© 2021 The Authors. Advanced Synthesis & Catalysis
published by Wiley-VCH GmbH
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