Yu et al. Sci China Chem
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(101ꢀMHz, DMSO) δ 154.81, 133.07, 131.36, 129.50,
119.53, 119.51, 85.03, 81.68.
4.41 (s, 2H). 13C NMR (101ꢀMHz, DMSO) δ 154.79, 146.37,
132.94, 127.19, 117.47, 85.28, 81.89, 62.85.
3-(p-Tolyl)propiolic acid (3b):
142.4ꢀmg, 89%,
3-(Biphenyl-4-yl)propiolic acid (3l): 204.2ꢀmg, 92%,
white solid. 1H NMR (400ꢀMHz, CDCl3) δ 7.69 (d,
J=8.3ꢀHz, 2H), 7.65–7.57 (m, 4H), 7.47 (t, J=7.4ꢀHz, 2H),
7.39 (t, J=7.3ꢀHz, 1H). 13C NMR (101ꢀMHz, CDCl3) δ
156.93, 143.80, 139.76, 133.68, 128.97, 128.20, 127.28,
127.14, 118.05, 88.27, 80.85.
white solid. 1H NMR (400ꢀMHz, CDCl3) δ 7.49 (d,
J=8.1ꢀHz, 2H), 7.21 (t, J=17.4ꢀHz, 2H), 2.38 (s, 3H). 13C
NMR (101ꢀMHz, CDCl3) δ 157.48, 141.61, 133.19, 129.40,
116.31, 88.54, 80.17, 21.72.
3-(4-Methoxyphenyl)propiolic acid (3c): 154.8ꢀmg, 88%,
white solid. 1H NMR (400ꢀMHz, CDCl3) δ 7.56 (d,
J=8.8ꢀHz, 2H), 6.89 (d, J=8.8ꢀHz, 2H), 3.84 (s, 3H). 13
3-(Nitrophenyl)propiolic acid (3m): 118.4ꢀmg, 62%, white
1
C
solid. H NMR (400ꢀMHz, CDCl3) δ 8.24 (d, J=8.8ꢀHz, 2H),
NMR (101ꢀMHz, CDCl3) δ 161.85, 157.84, 135.25, 114.38,
111.06, 89.51, 79.80, 55.41.
7.74 (d, J=8.8ꢀHz, 2H). 13C NMR (101ꢀMHz, CDCl3) δ
154.58, 153.77, 148.53, 133.68, 130.65, 126.42, 126.23,
123.71, 84.34, 83.22.
3-(4-Cyanophenyl)propiolic acid (3n): 137.2ꢀmg, 80%,
white solid. 1H NMR (400ꢀMHz, DMSO) δ 14.03 (s, 1H),
7.93 (d, J=8.4ꢀHz, 2H), 7.85 (d, J=8.4ꢀHz, 2H). 13C NMR
(101ꢀMHz, DMSO) δ 154.29, 133.65, 133.22, 124.32,
118.72, 113.50, 85.47, 82.50.
3-(4-Fluorophenyl)propiolic acid (3d): 216ꢀmg, 96%,
white solid. 1H NMR (400ꢀMHz, CDCl3) δ 7.50–7.44 (m,
2H), 7.41–7.35 (m, 2H). 13C NMR (101ꢀMHz, CDCl3) δ
155.40, 134.21, 131.90, 125.08, 118.92, 84.23, 82.33.
3-(3-Chlorophenyl)propiolic acid (3e): 178.4ꢀmg, 98%,
white solid. 1H NMR (400ꢀMHz, CDCl3) δ 7.59–7.56 (m,
1H), 7.51–7.42 (m, 2H), 7.32 (t, J=7.9ꢀHz, 1H). 13C NMR
(101ꢀMHz, CDCl3) δ 156.87, 134.58, 132.78, 131.18, 129.90,
121.14, 85.94, 81.16.
3-(4-Chlorophenyl)propiolic acid (3f): 175.1ꢀmg, 97%,
white solid. 1H NMR (400ꢀMHz, DMSO) δ 7.36 (dd,
J=16.1, 4.6ꢀHz, 1H), 7.28–7.19 (m, 1H). 13C NMR
(101ꢀMHz, DMSO) δ 154.92, 136.35, 133.79, 128.76,
118.23, 83.58, 82.15.
3-(2-Chlorophenyl)propiolic acid (3g): 176.2ꢀmg, 97%,
white solid. 1H NMR (400ꢀMHz, DMSO) δ 7.75 (dd,
J=7.7, 1.5ꢀHz, 1H), 7.64 (dd, J=8.1, 0.9ꢀHz, 1H), 7.56
(td, J=7.8, 1.6ꢀHz, 1H), 7.45 (td, J=7.6, 1.1ꢀHz, 1H). 13C
NMR (101ꢀMHz, DMSO) δ 153.49, 135.14, 134.15, 131.86,
129.12, 127.09, 118.49, 85.50, 79.89.
3-(2-(Trifluoromethyl)phenyl)propiolic
acid
(3o):
207.6ꢀmg, 97%, white solid. 1H NMR (400ꢀMHz, CDCl3)
δ 7.70 (d, J=8.2ꢀHz, 2H), 7.64 (d, J=8.4ꢀHz, 2H). 13C NMR
(101ꢀMHz, CDCl3) δ 155.87, 154.84, 133.20, 132.36, 132.03,
131.79, 126.56, 125.57, 125.54, 125.50, 125.46, 124.89,
123.51, 122.19, 84.60, 82.42.
3-(3-(Methoxycarbonyl)phenyl)propiolic
acid
(3p):
195.8ꢀmg, 96%, white solid. 1H NMR (400ꢀMHz, CDCl3)
δ 8.04 (d, J=8.4ꢀHz, 1H), 7.65 (d, J=8.4ꢀHz, 1H), 3.94 (s,
3H). 13C NMR (101ꢀMHz, CDCl3) δ 161.10, 155.15, 140.43,
132.81, 132.15, 131.66, 130.61, 129.59, 125.70, 124.30,
90.29, 82.86, 52.39
3-(Thiophen-2-yl)propiolic acid (3q): 144.4ꢀmg, 95%,
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white solid. H NMR (400ꢀMHz, CDCl3) δ 7.52 (dd, J=3.7,
3-(4-Fluorophenyl)propiolic acid (3h): 160.7ꢀmg, 98%,
white solid. 1H NMR (400ꢀMHz, CDCl3) δ 7.59 (dd,
J=8.8, 5.3ꢀHz, 2H), 7.07 (t, J=8.6ꢀHz, 2H). 13C NMR
(101ꢀMHz, CDCl3) δ 165.25, 162.73, 156.67, 156.62, 140.02,
135.43, 135.34, 133.41, 133.33, 127.98, 127.90, 116.24,
116.02, 86.25, 86.19, 80.67.
3-(3-Fluorophenyl)propiolic acid (3i): 159.1ꢀmg, 97%,
white solid. 1H NMR (400ꢀMHz, CDCl3) δ 7.33–7.25 (m,
2H), 7.21 (ddd, J=3.8, 2.1, 1.2ꢀHz, 1H), 7.10 (s, 1H). 13C
NMR (101ꢀMHz, CDCl3) δ 163.45, 160.98, 156.86, 130.42,
130.34, 129.03, 129.00, 121.26, 121.17, 119.88, 119.65,
118.47, 118.26, 86.06, 86.03, 80.92.
1.0ꢀHz, 1H), 7.48 (dd, J=5.1, 1.0ꢀHz, 1H), 7.06 (dd, J=5.0,
3.8ꢀHz, 1H). 13C NMR (101ꢀMHz, CDCl3) δ 156.84, 136.97,
131.59, 127.60, 119.24, 84.82, 81.88.
3-(Thiophen-3-yl)propiolic acid (3r): 146.1ꢀmg, 96%,
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white solid. H NMR (400ꢀMHz, CDCl3) δ 7.81 (dd, J=2.8,
0.9ꢀHz, 1H), 7.34 (dd, J=5.0, 3.0ꢀHz, 1H), 7.28–7.23 (m,
1H). 13C NMR (101ꢀMHz, CDCl3) δ 157.70, 134.60, 130.29,
126.25, 118.53, 84.14, 80.26.
3,3′-(1,4-Phenylene)dipropiolic acid (3u): 181.9ꢀmg, 85%,
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white solid. H NMR (400ꢀMHz, CDCl3) δ 7.55 (s, 1H). 13
C
NMR (101ꢀMHz, CDCl3) δ 154.44, 133.41, 121.62, 84.29,
83.51.
3-(2-Fluorophenyl)propiolic acid (3j): 160.2ꢀmg, 97%,
white solid. 1H NMR (400ꢀMHz, CDCl3) δ 7.61–7.55 (m,
1H), 7.47 (ddd, J=15.4, 5.3, 1.7ꢀHz, 1H), 7.21–7.10 (m,
2H). 13C NMR (101ꢀMHz, CDCl3) δ 164.12, 161.57, 156.50,
133.78, 132.10, 132.02, 123.35, 123.31, 115.05, 114.85,
107.28, 107.13, 83.66, 81.00.
3,3′,3′′-(1,3,5-Phenylene)tripropiolic
acid
(3v):
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248.1ꢀmg, 88%, white solid. H NMR (400ꢀMHz, CDCl3) δ
7.95 (s, 3H). 13C NMR (101ꢀMHz, CDCl3) δ 154.26, 137.97,
121.54, 83.63, 81.65.
Methyl 3-pyridylpropiolate (3s′): 115.6ꢀmg, 78%, brown
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solid. H NMR (400ꢀMHz, CDCl3) δ 8.77 (d, J=1.3ꢀHz, 1H),
3-(4-Hydroxymethylphenyl)propiolic
150.1ꢀmg, 85%, white solid. H NMR (400ꢀMHz, DMSO) δ
13.62 (s, 1H), 7.45 (d, J=7.9ꢀHz, 2H), 7.27 (d, J=8.1ꢀHz, 2H),
acid
(3k):
8.63 (dd, J=4.9, 1.5ꢀHz, 1H), 7.85 (dt, J=7.9, 1.8ꢀHz, 1H),
7.31 (dd, J=7.9, 4.9ꢀHz, 1H), 3.83 (s, 3H), 13C NMR
(101ꢀMHz, CDCl3) δ 153.84, 153.25, 150.67, 139.74, 123.12,
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