10.1002/ejoc.201800591
European Journal of Organic Chemistry
FULL PAPER
CH), 55.8 (q, 3H, Ar-OCH3) ppm. HR-MS (ESI+) m/z calculated for
[C22H17O2]+=[M+H]+: 313.1223; found 313.1223.
ether/ethyl acetate 96:4), Rf(2d)=0.9, Rf(3bd)=0.8, UV detection]. IR (MIR-
ATR, 4000–600 cm-1): max=2931, 2851, 1704, 1605, 1506, 1457, 1223,
1
1232, 1123, 1045, 832 cm-1. H NMR (CDCl3, 400 MHz): δ=7.35 (d, 1H,
6-Methoxy-2,3-bis(4-methylphenyl)-1H-inden-1-one (3bb): GP was
carried out with 2-bromo-5-methoxybenzaldehyde 1b (53.7 mg, 0.25
mmol), 1-methyl-4-[(4-methylphenyl)ethynyl]benzene 2b (127.7 mg, 0.62
mmol), Pd(OAc)2 (2.8 mg, 5 mol%), L-Proline (5.7 mg, 20 mol%), TBAI
(92.3 mg, 0.25 mmol), K2CO3 (138.6 mg, 1 mmol), and H2O (0.5 mL).
purification of the crude material by silica gel column chromatography
(petroleum ether/ethyl acetate, 100:0 to 98:2) gave the indene 3bb (53.4
mg, 63%) as a light yellow jelly compound, [TLC control (petroleum
ether/ethyl acetate 98:2), Rf(2b)=0.8, Rf(3bb)=0.7, UV detection]. IR (MIR-
ATR, 4000–600 cm-1): max=2926, 2850, 1704, 1614, 1506, 1458, 1293,
1259, 1187, 1031, 834 cm-1. 1H NMR (CDCl3, 400 MHz): δ=7.29-7.25 (m,
2H, Ar-H), 7.20 (m, 2H, Ar-H), 7.16 (m, 2H, Ar-H), 7.13 (s, 1H, Ar-H), 7.07
(s, 1H, Ar-H), 7.04 (m, 2H, Ar-H), 6.78 (dd, 1H, J=7.83 Hz, Ar-H), 3.84 (s,
3H, Ar-OCH3), 2.39 (s, 3H, Ar-CH3) 2.31 (s, 3H, Ar-CH3) ppm. 13C NMR
(CDCl3, 100 MHz): δ=196.4 (s, C=O), 160.8 (s, Ar-C), 155.8 (s, Ar-C),
139.3 (s, Ar-C), 137.2 (s, Ar-C), 137.1 (s, Ar-C), 133.1 (s, Ar-C), 131.0 (s,
Ar-C), 130.0 (s, Ar-C), 129.6 (d, 2C, 2 × Ar-CH), 129.4 (d, 2C, 2 × Ar-CH),
128.8 (d, 2C, 2 × Ar-CH), 128.4 (d, 2C, 2 × Ar-CH), 128.1 (s, Ar-C), 122.1
(d, Ar-CH), 116.1 (d, Ar-CH), 110.4 (d, Ar-CH), 55.8 (q, 3H, Ar-OCH3), 21.5
(q, 3H, Ar-CH3), 21.3 (q, 3H, Ar-CH3) ppm. HR-MS (ESI+) m/z calculated
for [C24H21O2]+=[M+H]+: 341.1536; found 341.1533.
J=2.45 Hz, Ar-H), 7.32 (d, 1H, J=2.44 Hz, Ar-H), 7.20 (d, 1H, J=1.96 Hz,
Ar-H), 7.18 (d, 1H, J=1.96 Hz, Ar-H), 7.15 (d, 1H, J=2.44 Hz, Ar-H), 7.05
(d, 1H, J=7.82 Hz, Ar-H), 6.92 (d, 1H, J=1.96 Hz, Ar-H), 6.90 (d, 1H, J=1.96
Hz, Ar-H), 6.81 (d, 1H, J=1.96 Hz, Ar-H), 6.79 (m, 1H, Ar-H), 6.76 (d, 1H,
J=2.44 Hz, Ar-H), 3.84 (2 × s, 6H, 2 × Ar-OCH3), 3.78 (s, 3H, Ar-OCH3)
ppm. 13C NMR (CDCl3, 100 MHz): δ=196.6 (s, C=O), 160.7 (s, Ar-C), 160.3
(s, Ar-C), 158.8 (s, Ar-C), 154.9 (s, Ar-C), 137.1 (s, Ar-C), 133.2 (s, Ar-C),
131.1 (d, 2C, 2 × Ar-CH), 130.1 (d, 2C, 2 × Ar-CH), 130.2 (s, Ar-C), 125.3
(s, Ar-C), 123.6 (s, Ar-C), 121.9 (d, Ar-CH), 116.1 (d, Ar-CH), 114.1 (d, 2C,
2 × Ar-CH), 113.6 (d, 2C, 2 × Ar-CH), 110.3 (d, Ar-CH), 55.8 (q, 3H, Ar-
OCH3), 55.3 (q, 3H, Ar-OCH3), 55.1 (q, 3H, Ar-OCH3) ppm. HR-MS (ESI+)
m/z calculated for [C24H21O4]+=[M+H]+: 373.1434; found 373.1364.
5,6-Dimethoxy-2,3-diphenyl-1H-inden-1-one (3ca): GP was carried out
with 2-bromo-4,5-dimethoxybenzaldehyde 1c (61 mg, 0.25 mmol), 1,2-
diphenylethyne 2a (111.2 mg, 0.62 mmol), Pd(OAc)2 (2.8 mg, 5 mol%), L-
Proline (5.7 mg, 20 mol%), TBAI (92.3 mg, 0.25 mmol), K2CO3 (138.6 mg,
1 mmol), and H2O (0.5 mL). purification of the crude material by silica gel
column chromatography (petroleum ether/ethyl acetate, 100:0 to 95:5)
gave the indene 3ca (68.9 mg, 81%) as a light yellow jelly compound, [TLC
control (petroleum ether/ethyl acetate 95:5), Rf(2a)=0.9, Rf(3ca)=0.8, UV
detection]. IR (MIR-ATR, 4000–600 cm-1): max=2922, 2855, 1712, 1612,
1458, 1327, 1184, 732, 702, 515 cm-1. 1H NMR (CDCl3, 400 MHz): δ=7.42-
7.35 (m, 5H, Ar-H), 7.25-7.21 (m, 6H, Ar-H), 6.68 (s, 1H, Ar-H), 3.93 (s,
3H, Ar-OCH3), 3.87 (s, 3H, Ar-OCH3) ppm. 13C NMR (CDCl3, 100 MHz):
δ=195.9 (s, C=O), 154.0 (s, Ar-C), 152.8 (s, Ar-C), 149.2 (s, Ar-C), 139.7
(s, Ar-C), 132.9 (s, Ar-C), 131.3 (s, Ar-C), 130.9 (s, Ar-C), 129.8 (d, 2 × Ar-
CH), 129.1 (d, Ar-CH), 128.8 (d, 2 × Ar-CH), 128.3 (d, 2 × Ar-CH), 128.0
(d, 2C, 2 × Ar-CH), 127.4 (d, Ar-CH), 123.0 (s, Ar-C), 107.7 (d, Ar-CH),
106.0 (d, Ar-CH), 56.4 (q, 3H, Ar-CH3), 56.3 (q, 3H, Ar-CH3) ppm. HR-MS
(ESI+) m/z calculated for [C23H19O3]+=[M+H]+: 343.1329; found 343.1325.
5,6-Dimethoxy-2,3-bis(4-methylphenyl)-1H-inden-1-one (3cb): GP
was carried out with 2-bromo-4,5-dimethoxybenzaldehyde 1c (61 mg, 0.25
mmol), 1-methyl-4-[(4-methylphenyl)ethynyl]benzene 2b (127.7 mg, 0.62
mmol), Pd(OAc)2 (2.8 mg, 5 mol%), L-Proline (5.7 mg, 20 mol%), TBAI
(92.3 mg, 0.25 mmol), K2CO3 (138.6 mg, 1 mmol), and H2O (0.5 mL).
purification of the crude material by silica gel column chromatography
(petroleum ether/ethyl acetate, 100:0 to 95:5) gave the indene 3cb (71.6
mg, 78%) as a light yellow jelly compound, [TLC control (petroleum
ether/ethyl acetate 94:6), Rf(2b)=0.9, Rf(3cb)=0.8, UV detection]. IR (MIR-
ATR, 4000–600 cm-1): max=2932, 2856, 1704, 1614, 1505, 1468, 1283,
1249, 1177, 1031, 799 cm-1. 1H NMR (CDCl3, 400 MHz): δ=7.28-7.25 (m,
2H, Ar-H), 7.22-7.19 (m, 3H, Ar-H), 7.14 (d, 2H, J=8.31 Hz Ar-H), 7.05 (d,
2H, J=8.32 Hz, Ar-H), 6.69 (s, 1H, Ar-H), 3.92 (s, 3H, Ar-OCH3) 3.87 (s,
3H, Ar-OCH3), 2.40 (s, 3H, Ar-CH3) 2.30 (s, 3H, Ar-CH3) ppm. 13C NMR
(CDCl3, 100 MHz): δ=196.2 (s, C=O), 153.4 (s, Ar-C), 152.6 (s, Ar-C),
149.0 (s, Ar-C), 139.9 (s, Ar-C), 139.1 (s, Ar-C), 137.1 (s, Ar-C), 131.0 (s,
Ar-C), 130.0 (s, Ar-C), 129.6 (d, 2C, 2 × Ar-CH), 129.5 (d, 2C, 2 × Ar-CH),
128.7 (d, 2C, 2 × Ar-CH), 128.3 (d, 2C, 2 × Ar-CH), 128.2 (s, Ar-C), 123.2
(s, Ar-C), 107.5 (d, Ar-CH), 105.9 (d, Ar-CH), 56.4 (q, Ar-CH3), 56.3 (q, Ar-
6-Methoxy-2,3-bis(3-methylphenyl)-1H-inden-1-one (3bc): GP was
carried out with 2-bromo-5-methoxybenzaldehyde 1b (53.7 mg, 0.25
mmol), 1-methyl-3-[(3-methylphenyl)ethynyl]benzene 2c (127.7 mg, 0.62
mmol), Pd(OAc)2 (2.8 mg, 5 mol%), L-Proline (5.7 mg, 20 mol%), TBAI
(92.3 mg, 0.25 mmol), K2CO3 (138.6 mg, 1 mmol), and H2O (0.5 mL).
purification of the crude material by silica gel column chromatography
(petroleum ether/ethyl acetate, 100:0 to 98:2) gave the indene 3bc (50.9
mg, 60%) as a light yellow jelly compound, [TLC control (petroleum
ether/ethyl acetate 98:2), Rf(2c)=0.8, Rf(3bc)=0.7, UV detection]. IR (MIR-
ATR, 4000–600 cm-1): max=2934, 2851, 1704, 1608, 1525, 1459, 1294,
1259, 1187, 1030, 834 cm-1. 1H NMR (CDCl3, 400 MHz): δ=7.25 (t, 1H,
J=5.38 Hz, Ar-H), 7.20-7.17 (m, 3H, Ar-H), 7.14-7.09 (m, 3H, Ar-H), 7.04-
6.97 (m, 3H, Ar-H), 6.79 (dd, 1H, J=7.83 Hz, Ar-H), 3.85 (s, 3H, Ar-OCH3),
2.34 (s, 3H, Ar-CH3), 2.30 (s, 3H, Ar-CH3) ppm. 13C NMR (CDCl3, 100
MHz): δ=196.3 (s, C=O), 160.9 (s, Ar-C), 156.4 (s, Ar-C), 138.3 (s, Ar-C),
137.4 (s, Ar-C), 137.1 (s, Ar-C), 133.0 (s, Ar-C), 132.9 (s, Ar-C), 131.4 (s,
Ar-C), 130.9 (s, Ar-C), 130.4 (d, Ar-CH), 130.0 (d, Ar-CH), 128.7 (d, Ar-
CH), 128.5 (d, Ar-CH), 128.2 (d, Ar-CH), 127.8 (d, Ar-CH), 126.8 (d, Ar-
CH), 125.6 (d, Ar-CH), 122.2 (d, Ar-CH), 116.2 (d, Ar-CH), 110.5 (d, Ar-
CH), 55.8 (q, 3H, Ar-OCH3), 21.4 (2 × q, 6H, 2 × Ar-CH3) ppm. HR-MS
(ESI+) m/z calculated for [C24H21O2]+=[M+H]+: 341.1536; found 341.1533.
6-Methoxy-2,3-bis(4-methoxyphenyl)-1H-inden-1-one (3bd): GP was
carried out with 2-bromo-5-methoxybenzaldehyde 1b (92.3 mg, 0.25
mmol), 1-methoxy-4-[(4-methoxyphenyl)ethynyl]benzene 2d (147.5 mg,
0.62 mmol), Pd(OAc)2 (2.8 mg, 5 mol%), L-Proline (5.7 mg, 20 mol%),
TBAI (56.7 mg, 0.25 mmol), K2CO3 (138.6 mg, 1 mmol), and H2O (0.5 mL).
purification of the crude material by silica gel column chromatography
(petroleum ether/ethyl acetate, 100:0 to 97:3) gave the indene 3bd (57.5
mg, 62%) as a light yellow jelly compound, [TLC control (petroleum
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