10.1002/adsc.202000186
Advanced Synthesis & Catalysis
129.46, 129.39, 128.52, 128.42, 127.10, 126.95, 126.15,
125.71, 39.34, 21.43.
128.70, 128.50, 128.43, 127.92, 126.87, 126.18, 123.31,
39.39, 21.41.
1-cinnamyl-3-fluorobenzene (3k) [59]: pale yellow oil, 35
mg, 84%. 1H NMR (400 MHz, CDCl3): δ 7.37-7.35 (m,
2H), 7.31-7.19 (m, 4H), 7.00 (d, J = 7.6 Hz, 1H), 6.96-6.88
(m, 2H), 6.46 (d, J = 16 Hz, 1H), 6.35-6.28 (m, 1H), 3.54
(d, J = 6.4 Hz, 2H), ppm; 13C NMR (100 MHz, CDCl3): δ
163.02 (d, J = 244.2 Hz), 142.77(d, J = 7.1 Hz), 137.26,
131.67, 129.89 (d, J = 8.3 Hz), 128.57, 128.28, 127.31,
126.19, 124.29 (d, J = 2.7 Hz), 115.53 (d, J = 21 Hz),
113.10 (d, J = 21 Hz), 39.02 (d, J = 1.6 Hz). 19F NMR (376
MHz, CDCl3): δ -113.49.
(E)-1-methyl-2-(3-phenylprop-1-en-1-yl)benzene
1
(4h)[65]: colorless oil, 32 mg, 77%. H NMR (400 MHz,
CDCl3): δ 7.44-7.40 (m, 1H), 7.33-7.29 (m, 2H), 7.26-7.20
(m, 3H), 7.16-7.12 (m, 3H), 6.66 (d, J = 15.6 Hz, 1H),
6.26-6.19 (m, 1H), 3.57 (d, J = 6.8 Hz, 2H), 2.34 (s, 1H),
ppm; 13C NMR (100 MHz, CDCl3): δ 140.34, 136.64,
135.12, 130.54, 130.21, 129.05, 128.65, 128.51, 127.08,
126.18, 126.06, 125.62, 39.68, 19.87.
(E)-1-methoxy-4-(3-phenylprop-1-en-1-yl)benzene
1
(4i)[66]: colorless oil, 32 mg, 72%. H NMR (400 MHz,
1-cinnamyl-2-fluorobenzene (3l) [60]: pale yellow oil, 26
CDCl3): δ 7.25-7.20 (m, 4H), 7.18-7.11 (m, 3H), 6.78-6.74
(m, 2H), 6.33 (d, J = 16 Hz, 1H), 6.18-6.10 (m, 1H), 3.72
(s, 3H), 3.45 (d, J = 6.8 Hz, 2H), ppm; 13C NMR (100
MHz, CDCl3): δ 157.81, 139.42, 129.40, 129.28, 127.61,
127.41, 126.19, 126.01, 125.07, 112.88, 54.22, 38.29.
1
mg, 62%. H NMR (400 MHz, CDCl3): δ 7.36-7.34 (m,
2H), 7.30-7.26 (m, 2H), 7.25-7.17 (m, 3H), 7.10-7.01 (m,
2H), 6.46 (d, J = 16 Hz, 1H), 6.37-6.30 (m, 1H), 3.56 (d, J
= 6.8 Hz, 2H), ppm; 13C NMR (100 MHz, CDCl3): δ
161.00 (d, J = 243.7 Hz), 137.35, 131.44, 130.67 (d, J =
4.7 Hz), 128.51, 127.90 (d, J = 8.0 Hz), 127.60, 127.19,
127.16, 127.00, 126.15, 124.09 (d, J = 3.6 Hz), 115.30 (d,
J = 21.8 Hz), 32.24 (d, J = 3.1 Hz). 19F NMR (376 MHz,
CDCl3): δ -118.41.
(E)-1-chloro-4-(3-phenylprop-1-en-1-yl)benzene (4j) [67]
:
1
colorless oil, 31 mg, 68%. H NMR (400 MHz, CDCl3): δ
7.34-7.20 (m, 9H), 6.39 (d, J = 16 Hz, 1H), 6.36-6.29 (m,
1H), 3.53 (d, J = 6 Hz, 2H), ppm; 13C NMR (100 MHz,
CDCl3): δ 139.89, 136.00, 132.68, 130.05, 129.86, 128.69,
128.66, 128.58, 127.35, 126.31, 39.34.
1-cinnamyl-2-methylbenzene (3m) [58]: colorless oil, 36
1
mg, 87%. H NMR (400 MHz, CDCl3): δ 7.35-7.32 (m,
(E)-1-chloro-3-(3-phenylprop-1-en-1-yl)benzene (4k)[68]
:
1
2H), 7.29-7.26 (m, 2H), 7.21-7.12 (m, 5H), 6.39-6.29 (m,
2H), 3.52 (d, J = 4.5 Hz, 2H), 2.33 (s, 3H), ppm; 13C NMR
(100 MHz, CDCl3): δ 138.26, 137.57, 136.45, 130.92,
130.25, 129.25, 128.58, 128.51, 127.07, 126.44, 126.13,
126.10, 36.90, 19.48.
colorless oil, 29 mg, 65%. H NMR (400 MHz, CDCl3): δ
7.34-7.30 (m, 3H), 7.25-7.19 (m, 5H), 7.18-7.15 (m, 1H),
6.39-6.37 (m, 2H), 3.54 (d, J = 4.8 Hz, 2H), ppm; 13C
NMR (100 MHz, CDCl3): δ 139.73, 139.37, 134.47,
130.93, 129.77, 129.71, 128.68, 128.58, 127.05, 126.33,
126.08, 124.35, 39.29.
3-cinnamylthiophene (3n) [51]: colorless oil, 19 mg, 48%;
1
in the presence of 0.2 mmol Zn powder: 19 mg, 49%. H
(E)-1,3-dimethoxy-2-(3-phenylprop-1-en-1-yl)benzene
1
NMR (400 MHz, CDCl3): δ 7.38-7.36 (m, 2H), 7.32-7.27
(m, 3H), 7.23-7.19 (m, 1H), 7.03-6.98 (m, 2H), 6.47 (d, J =
16 Hz, 1H), 6.40-6.33 (m, 1H), 3.56 (d, J = 6.8 Hz, 2H),
ppm; 13C NMR (100 MHz, CDCl3): δ 140.55, 137.44,
131.07, 128.53, 128.36, 127.16, 126.14, 125.59, 120.88,
33.84.
(4m) [69]: colorless oil, 43 mg, 85%. H NMR (400 MHz,
CDCl3): δ 7.24-7.19 (m, 4H), 7.13-7.09 (m, 1H), 7.03 (d, J
= 8.4 Hz, 1H), 6.73-6.67 (m, 2H), 6.46 (d, J = 8.4 Hz, 2H),
3.74 (s, 6H), 3.51 (dd, J = 3.6 Hz, 2 Hz, 2H), ppm; 13C
NMR (100 MHz, CDCl3): δ 157.27, 140.13, 132.30,
127.61, 127.28, 126.44, 124.80, 120.54, 113.75, 102.96,
2-cinnamylnaphthalene (3o) [51]: white solid, 40 mg, 82%, 54.69, 40.10.
M.P.=39.5-40.2 ºC. 1H NMR (400 MHz, CDCl3): δ
7.82-7.77 (m, 3H), 7.67 (s, 1H), 7.47-7.40 (m, 2H),
7.39-7.36 (m, 3H), 7.31-7.27 (m, 2H), 7.22-7.18 (m, 1H),
6.49 (d, J = 15.6 Hz, 1H), 6.46-6.39 (m, 1H), 3.70 (d, J = 6
Hz, 2H), ppm; 13C NMR (100 MHz, CDCl3): δ 137.68,
137.48, 133.70, 132.20, 131.35, 129.09, 128.55, 128.07,
127.67, 127.53, 127.49, 127.18, 126.77, 126.19, 126.02,
125.36, 39.50.
(E)-1-fluoro-4-(3-phenylprop-1-en-1-yl)benzene
(4n)
[63]: colorless oil, 27 mg, 64%. 1H NMR (400 MHz,
CDCl3): δ 7.33-7.28 (m, 4H), 7.24-7.20 (m, 3H), 7.00-6.94
(m, 2H), 6.40 (d, J = 15.6 Hz, 1H), 6.30-6.23 (m, 1H), 3.53
(d, J = 6.8 Hz, 2H), ppm; 13C NMR (100 MHz, CDCl3): δ
162.07 (d, J = 244.5 Hz), 140.09, 133.66 (d, J = 3.3 Hz),
129.89, 129.05 (d, J = 2.2 Hz), 128.69, 128.56, 127.62,
127.55, 126.27,115.39 (d, J = 21.4 Hz), 39.32. 19F NMR
(376 MHz, CDCl3): δ -115.30.
(E)-prop-1-ene-1,3-diyldibenzene (4a) [51]: colorless oil,
from 2a: 35 mg, 90%; from 2c: 34 mg, 88%. 1H NMR (400
MHz, CDCl3): δ 7.37-7.18 (m, 10H), 6.46 (d, J = 16 Hz,
(E)-1-(3-phenylprop-1-en-1-yl)-4
(trifluoromethyl)benzene (4o) [66]: colorless oil, 20 mg,
39%. 1H NMR (400 MHz, CDCl3): δ 7.53 (d, J = 8.4 Hz,
2H), 7.43 (d, J = 8 Hz, 2H), 7.35-7.31 (m, 2H), 7.25-7.22
(m, 3H), 6.47-6.46 (m, 2H), 3.56 (d, J = 4 Hz, 2H), ppm;
13C NMR (100 MHz, CDCl3): δ 140.94, 139.55, 132.14,
129.82, 128.77 (q, J = 13.4 Hz), 128.52, 128.43, 126.22,
126.07, 125.28 (q, J = 3.8 Hz), 122.73, 39.17; 19F NMR
1H), 6.39-6.32 (m, 1H), 3.55 (d, J = 6.4 Hz, 2H), ppm; 13
C
NMR (100 MHz, CDCl3): δ 140.31, 137.62, 131.21,
129.37, 128.82, 128.64, 127.25, 126.32, 126.27, 39.50.
(E)-but-1-ene-1,3-diyldibenzene (4b) [61]: light yellow oil,
1
from 2b: 32 mg, 78%; from 2c: 31 mg, 75%. H NMR
(400 MHz, CDCl3): δ 7.36-7.33 (m, 2H), 7.32-7.26 (m,
6H), 7.23-7.17 (m, 2H), 6.44-6.35 (m, 2H), 3.67-3.61 (m,
1H), 1.46 (d, J = 7.2 Hz, 3H), ppm; 13C NMR (100 MHz,
CDCl3): δ 145.66, 137.60, 135.26, 128.51, 127.33, 127.07,
126.25, 126.17, 42.59, 21.25.
(376 MHz, CDCl3): δ -62.42.
[64]
methyl (E)-4-(3-phenylprop-1-en-1-yl)benzoate (4p)
:
light yellow oil, 35 mg, 71%. 1H NMR (400 MHz,
CDCl3): δ 7.95 (d, J = 8.4 Hz, 2H), 7.39 (d, J = 8.8 Hz,
2H), 7.33-7.30 (m, 2H), 7.24-7.20 (m, 3H), 6.49-6.47 (m,
2H), 3.89 (s, 3H), 3.56 (d, J = 5.2 Hz, 2H), ppm; 13C NMR
(100 MHz, CDCl3): δ 166.96, 142.01, 139.61, 132.25,
130.25, 129.93, 128.74, 128.62, 126.40, 126.02, 52.04,
39.46.
(E)-3-(3-phenylprop-1-en-1-yl)thiophene (4e)[62]
: pale
1
yellow oil, 24 mg, 61%. H NMR (400 MHz, CDCl3): δ
7.32-7.29 (m, 2H), 7.24-7.21 (m, 4H), 7.19-7.17 (m, 1H),
7.08 (d, J = 2.8 Hz, 1H), 6.45 (d, J = 15.6 Hz, 1H),
6.25-6.17 (m, 1H), 3.51 (d, J = 6.8 Hz, 2H), ppm; 13C
NMR (100 MHz, CDCl3): δ 140.18, 140.09, 129.23,
128.70, 128.51, 126.20, 125.87, 125.35, 125.00, 121.06,
39.26.
Analytical methods
(E)-1-methyl-4-(3-phenylprop-1-en-1-yl)benzene (4f)[63]
:
1
colorless oil, 34 mg, 83%. H NMR (400 MHz, CDCl3): δ
7.32-7.28 (m, 2H), 7.26-7.19 (m, 5H), 7.09 (d, J = 8 Hz,
2H), 6.42 (d, J = 16 Hz, 1H), 6.33-6.26 (m, 1H), 3.53 (d, J
= 6.8 Hz, 2H), 2.32 (s, 3H), ppm; 13C NMR (100 MHz,
CDCl3): δ 140.37, 136.86, 134.72, 130.94, 129.21, 128.68,
128.48, 128.19, 126.15, 126.04, 39.37, 21.17.
NMR spectra were recorded on a Bruker Avance III HD
400 spectrometer using TMS as an internal standard (400
1
MHz for H NMR and 100 MHz for 13C NMR). Mass
spectroscopy data were collected on
a Shimadzu
LCMS-IT-TOF mass spectrometer. Single crystal
structures were determined on a Bruker D8 Venture X-ray
diffractometer equipped with a PHOTON II CPAD
detector.
(E)-1-methyl-3-(3-phenylprop-1-en-1-yl)benzene
1
(4g)[64]: colorless oil, 28 mg, 69%. H NMR (400 MHz,
CDCl3): δ 7.32-7.29 (m, 2H), 7.25-7.14 (m, 6H), 7.02-7.01
(m, 1H), 6.43 (d, J = 16 Hz, 1H), 6.37-6.30 (m, 1H), 3.54
(d, J = 6.4 Hz, 2H), 2.32 (s, 3H), ppm; 13C NMR (100
MHz, CDCl3): δ 140.27, 138.05, 137.44, 131.15, 129.05,
Acknowledgements
9
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