10.1002/cctc.202000254
ChemCatChem
FULL PAPER
NMR (400 MHz, CDCl3) δ 7.92 (d, J = 9.0 Hz, 2H), 6.90 (d, J = 8.9 Hz, 2H),
6.76 (dd, J = 4.5, 1.9 Hz, 3H), 3.84 (s, 3H), 3.83 (s, 3H), 3.83 (s, 3H), 3.20
(t, J = 7.6 Hz, 2H), 2.98 (t, J = 7.7 Hz, 2H). 13C NMR (101 MHz, CDCl3) δ
198.05, 163.52, 148.95, 147.43, 134.16, 130.38, 130.05, 120.25, 113.80,
111.91, 111.41, 100.00, 55.90, 40.40, 30.08.
1-(4-chlorophenyl)-3-(3,4-dimethoxyphenyl) propan-1-one (3dd)[35f]
Yield 268.2 mg 88% (Catalyst Ru1), 277.3 mg 91% (Catalyst Ru2); 1H
NMR (500 MHz, CDCl3) δ 7.88 (d, J = 8.3 Hz, 2H), 7.41 (d, J = 8.4 Hz, 2H),
6.79 (d, J = 9.1 Hz, 3H), 3.87 (s, 3H), 3.85 (s, 3H), 3.25 (t, J = 7.6 Hz, 2H),
3.01 (t, J = 7.5 Hz, 2H). 13C NMR (126 MHz, CDCl3) δ 198.09, 148.94,
147.47, 139.45, 135.20, 133.67, 129.45, 128.90, 120.19, 111.86, 111.39,
55.92, 55.84, 40.64, 29.71.
1-(4-bromophenyl)-3-(3-methoxyphenyl)propan-1-one (3ee) Yield
261.7 mg 82% (Catalyst Ru1), 284 mg 89% (Catalyst Ru2); 1H NMR (400
MHz, CDCl3) δ 7.79 (d, J = 8.7 Hz, 2H), 7.57 (d, J = 8.7 Hz, 2H), 7.22 (dd,
J = 24.4, 16.5 Hz, 2H), 6.76 (dd, J = 18.7, 11.8 Hz, 3H), 3.78 (s, 3H), 3.24
(t, J = 7.6 Hz, 2H), 3.01 (t, J = 7.2 Hz, 2H). 13C NMR (101 MHz, CDCl3) δ
198.25, 159.82, 142.75, 135.60, 132.01, 129.65, 128.32, 120.82, 114.34,
111.51, 55.24, 40.42, 30.13. ESI-MS: 341.0154 [3ee+Na+]+ ion.
1-(4-fluorophenyl)-3-(3-methoxyphenyl)propan-1-one (3ef)[35c] Yield
206.6 mg 80% (Catalyst Ru1), 219.5 mg 85% (Catalyst Ru2);1H NMR (400
MHz, CDCl3) δ 7.97 (d, J = 8.9, 5.4 Hz, 2H), 7.21 (t, J = 7.8 Hz, 1H), 7.11
(t, J = 8.7 Hz, 2H), 6.84 – 6.73 (m, 3H), 3.79 (s, 3H), 3.26 (t, J = 7.4 Hz,
2H), 3.02 (t, J = 7.4 Hz, 2H). 13C NMR (101 MHz, CDCl3) δ 197.69, 167.08,
164.55, 159.81, 142.86, 133.35, 130.70, 129.70, 120.80, 114.36, 111.49,
55.21, 40.38, 30.20.
3-(3-chlorophenyl)-1-phenylpropan-1-one (3fa)[2a] Yield 208 mg 85%
(Catalyst Ru1), 212.9 mg 87% (Catalyst Ru2); 1H NMR (400 MHz, CDCl3)
δ 7.95 (d, J = 8.2 Hz, 2H), 7.56 (t, J = 7.4 Hz, 1H), 7.45 (t, J = 7.6 Hz, 2H),
7.24 (t, J = 2.8 Hz, 1H), 7.15 (dd, J = 17.0, 7.6 Hz, 2H), 3.29 (t, J = 7.6 Hz,
2H), 3.04 (t, J = 7.6 Hz, 2H). 13C NMR (101 MHz, CDCl3) δ 198.79, 143.44,
136.79, 134.31, 133.30, 129.87, 128.75, 128.12, 126.81, 126.47, 40.09,
29.74.
3-(3-chlorophenyl)-1-(p-tolyl)propan-1-one (3fb)[14g] Yield 217.3 mg
84% (Catalyst Ru1), 230.3 mg 89% (Catalyst Ru2); 1H NMR (500 MHz,
CDCl3) δ 7.89 (d, J = 7.6 Hz, 2H), 7.28 (d, J = 6.6 Hz, 3H), 7.25 – 7.14 (m,
3H), 3.29 (t, J = 7.6 Hz, 2H), 3.06 (t, J = 7.5 Hz, 2H), 2.43 (s, 3H). 13C NMR
(126 MHz, CDCl3) δ 198.34, 144.00, 143.51, 134.22, 129.78, 129.35,
128.60, 128.18, 126.75, 126.32, 39.88, 29.76, 29.54, 21.67.
3-(3-chlorophenyl)-1-(4-methoxyphenyl)propan-1-one (3fc)[9b] Yield
247.3 mg 90% (Catalyst Ru1), 252.8 mg 92% (Catalyst Ru2); 1H NMR
(500 MHz, CDCl3) δ 7.95 (d, J = 8.6 Hz, 2H), 7.27 – 7.13 (m, 4H), 6.94 (d,
J = 8.6 Hz, 2H), 3.86 (s, 3H), 3.24 (t, J = 7.6 Hz, 2H), 3.04 (t, J = 7.6 Hz,
2H). 13C NMR (126 MHz, CDCl3) δ 197.23, 163.55, 143.58, 134.18, 130.30,
129.77, 128.59, 126.75, 126.28, 113.78, 55.47, 39.61, 29.84.
1-(4-bromophenyl)-3-(3,4-dimethoxyphenyl)propan-1-one (3de) Yield
310.8 mg 89% (Catalyst Ru1), 317.8 mg 91% (Catalyst Ru2); 1H NMR
(500 MHz, CDCl3) δ 7.82 (d, J = 7.5 Hz, 2H), 7.60 (d, J = 7.5 Hz, 2H), 6.80
(dd, J = 13.9, 7.3 Hz, 3H), 3.88 (s, 3H), 3.87 (s, 3H), 3.26 (t, J = 7.5 Hz,
2H), 3.02 (t, J = 7.5 Hz, 2H). 13C NMR (126 MHz, CDCl3) δ 198.31, 148.95,
147.48, 135.61, 133.65, 131.92, 129.57, 128.22, 120.19, 111.86, 111.39,
55.94, 55.86, 40.65, 29.71. ESI-MS: 371.0387 [3de+Na+]+ ion.
3-(3,4-dimethoxyphenyl)-1-(4-fluorophenyl)propan-1-one (3df) Yield
247.9 mg 86% (Catalyst Ru1), 242.2 mg 84% (Catalyst Ru2);1H NMR (500
MHz, CDCl3) δ 8.03 – 7.98 (m, 2H), 7.14 (t, J = 8.1 Hz, 2H), 6.81 (dd, J =
12.8, 7.7 Hz, 3H), 3.89 (s, 3H), 3.87 (s, 3H), 3.27 (t, J = 7.5 Hz, 2H), 3.03
(t, J = 7.5 Hz, 2H). 13C NMR (126 MHz, CDCl3) δ 197.77, 166.74, 148.94,
147.46, 133.75, 133.33, 130.69, 130.62, 120.18, 115.78, 115.61, 111.85,
111.37, 55.94, 55.85, 40.62, 29.78. ESI-MS: 311.1056 [3df+Na+]+ ion.
3-(3-methoxyphenyl)-1-phenylpropan-1-one (3ea)[2c] Yield 199.5 mg
83% (Catalyst Ru1), 204.2 mg 85% (Catalyst Ru2); 1H NMR (400 MHz,
CDCl3) δ 8.00 (d, J = 8.5 Hz, 2H), 7.59 (t, J = 7.3 Hz, 1H), 7.49 (t, J = 7.6
Hz, 2H), 7.30 – 7.25 (m, 1H), 6.84 (dd, J = 7.9 Hz, 3H), 3.83 (s, 3H), 3.34
(t, 2H), 3.08 (t, J= 7.4, 2H). 13C NMR (101 MHz, CDCl3) δ 199.29, 159.84,
143.05, 136.92, 133.19, 129.63, 128.72, 128.15, 120.88, 114.34, 111.51,
55.25, 40.46, 30.26.
3-(3-methoxyphenyl)-1-(p-tolyl)propan-1-one (3eb) Yield 221.3 mg
87% (Catalyst Ru1), 228.9 mg 90% (Catalyst Ru2); 1H NMR (400 MHz,
CDCl3) δ 7.86 (d, J = 8.2 Hz, 2H), 7.23 (dd, J = 15.4, 7.8 Hz, 3H), 6.89 –
6.74 (m, 3H), 3.79 (s, 3H), 3.27 (t, J = 8.2 Hz, 2H), 3.03 (t, J = 7.4 Hz, 2H),
2.40 (s, 3H). 13C NMR (101 MHz, CDCl3) δ 198.94, 159.84, 143.92, 143.14,
134.49, 129.53, 128.26, 120.85, 114.35, 111.51, 55.23, 40.40, 30.27,
21.75. ESI-MS: 293.0970 [3eb+K+]+ ion.
3-(3-chlorophenyl)-1-(4-chlorophenyl)propan-1-one (3fd) Yield 240 mg
86% (Catalyst Ru1), 248.4 mg 89% (Catalyst Ru2); 1H NMR (500 MHz,
CDCl3) δ 7.91 (d, J = 7.7 Hz, 1H), 7.45 (d, J = 7.7 Hz, 1H), 7.28 (d, J = 7.4
Hz, 1H), 7.20 (d, J = 7.8 Hz, 1H), 3.27 (t, J = 7.5 Hz, 1H), 3.06 (t, J = 7.4
Hz, 1H). 13C NMR (126 MHz, CDCl3) δ 197.60, 139.51, 135.05, 131.98,
130.44, 129.82, 129.43, 128.98, 128.65, 115.00, 40.12, 29.29. ESI-MS:
279.0221 [3fd+H+]+ ion.
3-(3-methoxyphenyl)-1-(4-methoxyphenyl)propan-1-one (3ec)[9b] Yield
240.6 mg 89% (Catalyst Ru1), 245.9 mg 91% (Catalyst Ru2); 1H NMR
(400 MHz, CDCl3) δ 7.93 (d, J = 8.9 Hz, 2H), 7.21 (t, J = 7.9 Hz, 1H), 6.91
(d, J = 8.9 Hz, 2H), 6.87 – 6.71 (m, 3H), 3.85 (s, 3H), 3.78 (s, 3H), 3.24 (t,
J = 7.0 Hz, 2H), 3.05 – 3.00 (t, J = 8.2 Hz, 2H). 13C NMR (101 MHz, CDCl3)
δ 197.92, 163.54, 159.79, 143.20, 130.70, 130.40, 129.99, 129.59, 114.30,
113.81, 111.44, 55.56, 55.25, 40.13, 30.45.
1-(4-bromophenyl)-3-(3-chlorophenyl)propan-1-one (3fe) Yield 281.5
mg 87% (Catalyst Ru1), 291.3 mg 90% (Catalyst Ru2); 1H NMR (400 MHz,
CDCl3) δ 7.80 (d, J = 8.6 Hz, 2H), 7.58 (d, J = 8.6 Hz, 2H), 7.23 – 7.22 (m,
1H), 7.18 (t, J = 1.7 Hz, 1H), 7.14 – 7.09 (m, 2H), 3.24 (t, J = 7.6 Hz, 2H),
3.03 (t, J = 7.8 Hz, 2H). 13C NMR (101 MHz, CDCl3) δ 197.74, 143.17,
135.46, 134.35, 132.09, 129.62, 128.48, 40.06, 29.61. ESI-MS: 344.9727
[3fe+Na+]+ ion.
1-(4-chlorophenyl)-3-(3-methoxyphenyl)propan-1-one (3ed)[35a] Yield
222.5 mg 81% (Catalyst Ru1), 241.8 mg 88% (Catalyst Ru2); 1H NMR
(400 MHz, CDCl3) δ 7.87 (d, J = 8.6 Hz, 2H), 7.40 (d, J = 8.6 Hz, 2H), 7.20
(t, J = 7.8 Hz, 1H), 6.84 – 6.72 (m, 3H), 3.78 (s, 3H), 3.24 (t, J = 7.2 Hz,
2H), 3.01 (t, J = 8.0 Hz, 2H). 13C NMR (101 MHz, CDCl3) δ 198.04, 159.83,
142.78, 139.59, 135.21, 129.64, 129.54, 129.00, 120.83, 114.35, 111.51,
55.26, 40.42, 30.15.
3-(3-chlorophenyl)-1-(4-fluorophenyl)propan-1-one (3ff) Yield 220.7
mg 84% (Catalyst Ru1), 231.2 mg 88% (Catalyst Ru2); 1H NMR (500 MHz,
CDCl3) δ 8.03 – 7.98 (m, 2H), 7.27 – 7.20 (m, 3H), 7.15 (t, J = 8.0 Hz, 3H),
3.29 (t, J = 7.5 Hz, 2H), 3.06 (t, J = 7.5 Hz, 2H). 13C NMR (126 MHz, CDCl3)
δ 197.07 (s), 166.81 (s), 164.78 (s), 143.20 (s), 134.27, 130.69, 129.80,
128.57, 126.70, 26.41, 115.84, 115.67, 39.92, 29.63. ESI-MS: 285.0563
[3ff+Na+]+ ion.
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