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129.8, 129.5, 129.1, 128.8, 128.4, 126.5, 126.4, 126.4, 125.9, 125.2 (q, by column chromatography (petroleum ether) to give product 2a
JC,F = 3.7 Hz), 123.9 (q, JC,F = 270.4 Hz), 122.9, 92.6, 90.4, 51.9, as a white solid.
19.8 ppm. HRMS (EI): calcd. for C29H21F3 [M]+ 426.1590; found
1,1,2-Triphenyl-1H-indene (2a): White solid (90 %). 1H NMR
426.1594.
(400 MHz, CDCl3): δ = 7.39 (d, J = 7.4 Hz, 1 H), 7.37–7.33 (m, 2 H),
7.34–7.26 (m, 4 H), 7.25–7.12 (m, 12 H), 7.11–7.07 (m, 1 H) ppm. 13
C
1-Methyl-2-{phenyl[2-(p-tolylethynyl)phenyl]methyl}benzene
(3d): Yellow oil (361 mg, 90 %). H NMR (400 MHz, CDCl3): δ = 7.41
1
NMR (100 MHz, CDCl3): δ = 155.4, 155.0, 142.2, 142.1, 135.5, 129.0,
128.7, 128.2, 128.0, 127.9, 127.5, 127.1, 126.8, 126.1, 124.6, 121.6,
68.8 ppm. The data are consistent with those reported in the litera-
ture.[5]
(d, J = 3.1 Hz, 1 H), 7.16–7.07 (m, 7 H), 7.05–6.96 (m, 7 H), 6.76 (d,
J = 5.1 Hz, 1 H), 6.68 (d, J = 7.7 Hz, 1 H), 6.07 (s, 1 H), 2.22 (s, 3 H),
2.08 (s, 3 H) ppm. 13C NMR (100 MHz, CDCl3): δ = 147.6, 144.7, 143.9,
140.3, 138.9, 134.3, 133.3, 132.3, 131.8, 131.4, 131.1 131.0, 130.3,
130.0, 128.3, 128.2, 128.2, 127.7, 125.8, 122.2, 96.2, 89.3, 53.8, 23.5,
21.8 ppm. HRMS (EI): calcd. for C29H24 [M]+ 372.1873; found
372.1875.
2-(4-Methoxyphenyl)-1,1-diphenyl-1H-indene (2b): Yellow solid
(65 mg, 87 %). m.p. 172–173 °C. 1H NMR (400 MHz, CDCl3): δ = 7.37
(d, J = 7.5 Hz, 1 H), 7.31 (ddd, J = 7.1, 4.2, 2.3 Hz, 6 H), 7.25–7.12
(m, 9 H), 7.10–7.04 (m, 1 H), 6.75–6.66 (m, 2 H), 3.71 (s, 3 H) ppm.
13C NMR (100 MHz, CDCl3): δ = 159.0, 155.2, 154.6, 142.4, 142.2,
129.1, 128.7, 128.1, 128.0, 127.2, 127.0, 126.7, 125.7, 124.5, 121.2,
113.4, 68.7, 55.2 ppm. HRMS (EI): calcd. for C28H22O [M]+ 374.1665;
found 374.1668.
1-Methyl-2-{phenyl[2-(m-tolylethynyl)phenyl]methyl}benzene
(3e): Yellow oil (374 mg, 84 %). 1H NMR (400 MHz, CDCl3): δ = 7.46–
7.37 (m, 1 H), 7.17–7.12 (m, 2 H), 7.11–6.96 (m, 12 H), 6.77–6.75 (m
1 H), 6.68 (d, J = 7.3 Hz, 1 H), 6.06 (s, 1 H), 2.19 (s, 3 H), 2.08 (s, 3 H)
ppm. 13C NMR (100 MHz, CDCl3): δ = 147.6, 144.6, 143.9, 139.9,
138.9, 134.3, 134.1, 132.3, 131.8, 131.4, 131.1, 131.1, 130.4, 130.3,
130.1, 128.3, 128.3, 128.2, 127.7, 125.7, 125.0, 96.3, 89.7, 53.8, 23.2,
21.8 ppm. HRMS (EI): calcd. for C29H24 [M]+ 372.1873; found
372.1869.
1,1-Diphenyl-2-(p-tolyl)-1H-indene (2c): Yellow solid (50 mg,
1
70 %). m.p. 172–174 °C. H NMR (400 MHz, CDCl3): δ = 7.38 (d, J =
7.4 Hz, 1 H), 7.35–7.25 (m, 6 H), 7.25–7.12 (m, 9 H), 7.08 (td, J = 7.5,
1.1 Hz, 1 H), 6.97 (d, J = 8.0 Hz, 2 H), 2.24 (s, 3 H) ppm. 13C NMR
(100 MHz, CDCl3): δ = 155.39, 154.91, 142.28, 142.16, 137.28, 132.47,
128.75, 128.71, 128.10, 127.76, 126.99, 126.68, 125.91, 124.52,
121.34, 68.67, 21.19 ppm. HRMS (EI): calcd. for C28H22 [M]+ 358.1716;
found 358.1720.
1-Methyl-2-{phenyl[2-(o-tolylethynyl)phenyl]methyl}benzene
1
(3f): Yellow oil (370 mg, 83 %); a mixture of isomers (3:2). H NMR
(400 MHz, CDCl3): δ = 8.03 (d, J = 7.5 Hz, 0.6 H), 7.45–7.42 (m, 1 H),
7.20 (d, J = 7.2 Hz, 1 H), 7.12–6.91 (m, 21 H), 6.80–6.73 (m, 1 H),
6.71–6.62 (m, 2.6 H), 6.08 (s, 1 H), 5.64 (s, 0.6 H), 2.20 (s, 1.8 H), 2.18
(s, 3 H), 2.05 (s, 3 H), 2.03 (s, 1.8 H) ppm. 13C NMR (100 MHz, CDCl3):
δ = 147.0, 144.9, 144.7, 144.4, 144.1, 143.9, 143.4, 141.9, 141.8, 139.0,
138.9, 138.3, 134.5, 134.0, 133.8, 132.3, 131.9, 131.7, 131.5, 131.4,
131.3, 131.1, 131.0, 130.3, 130.2, 130.2, 130.1, 129.9, 129.8, 128.4,
128.3, 128.3, 128.2, 128.2, 127.9, 127.8, 127.6, 127.4, 127.4, 126.1,
125.9, 125.0, 100.1, 95.6, 94.8, 93.8, 53.7, 52.7, 22.8, 22.6, 21.8,
21.7 ppm. HRMS (EI): calcd. for C29H24 [M]+ 372.1873; found
372.1875.
1,1-Diphenyl-2-[4-(trifluoromethyl)phenyl]-1H-indene (2d): Col-
orless oil (67 mg, 81 %). 1H NMR (400 MHz, CDCl3): δ = 7.50–7.37
(m, 5 H), 7.33–7.27 (m, 5 H), 7.26–7.15 (m, 8 H), 7.15–7.11 (m, 1 H)
ppm. 13C NMR (100 MHz, CDCl3): δ = 155.6, 153.3, 141.5, 141.4,
138.8, 130.8, 129.0 (q, JC,F = 32.2 Hz), 128.6, 128.3, 127.9, 127.2,
127.0, 126.8, 124.9 (q, JC,F = 3.8 Hz), 124.6, 124.0 (q, JC,F = 270.3 Hz),
121.9, 68.7 ppm. HRMS (EI): calcd. for C28H19F3 [M]+ 412.1433; found
412.1428.
1,1-Diphenyl-2-(o-tolyl)-1H-indene (2e): White solid (56 mg,
1
78 %). m.p. 113–115 °C. H NMR (400 MHz, CDCl3): δ = 7.41 (d, J =
1-Ethyl-2-{phenyl[2-(phenylethynyl)phenyl]methyl}benzene
(3g): Yellow oil (390 mg, 77 %). 1H NMR (400 MHz, CDCl3): δ = 7.57–
7.52 (m, 1 H), 7.36–7.24 (m, 7 H), 7.24–7.17 (m, 5 H), 7.12–7.07 (m,
3 H), 6.93–6.88 (m, 1 H), 6.83 (d, J = 7.4 Hz, 1 H), 6.29 (s, 1 H), 2.71–
2.51 (m, 2 H), 1.06 (t, J = 7.5 Hz, 3 H) ppm. 13C NMR (100 MHz,
CDCl3): δ = 145.9, 143.2, 142.4, 141.3, 132.5, 131.5, 129.8, 129.6,
129.5, 128.3, 128.3, 128.3, 128.2, 126.6, 126.3, 126.3, 125.6, 123.5,
123.3, 94.1, 88.1, 51.0, 25.5, 14.5 ppm. HRMS (EI): calcd. for C29H24
[M]+ 372.1873; found 372.1870.
7.4 Hz, 1 H), 7.26 (td, J = 7.5, 1.1 Hz, 1 H), 7.23 (d, J = 7.7 Hz, 1 H),
7.20–7.06 (m, 12 H), 7.05–6.93 (m, 3 H), 6.74 (s, 1 H), 1.52 (s, 3 H)
ppm. 13C NMR (100 MHz, CDCl3): δ = 153.1, 153.0, 142.6, 141.1,
138.2, 136.8, 131.5, 130.0, 128.6, 128.3, 128.0, 127.3, 127.0, 126.7,
125.8, 125.6, 124.8, 121.7, 71.4, 19.6 ppm. HRMS (EI): calcd. for
C
28H22 [M]+ 358.1716; found 358.1713.
2-(2-Methoxyphenyl)-1,1-diphenyl-1H-indene (2f): Yellow oil
1
(63 mg, 84 %). H NMR (400 MHz, CDCl3): δ = 7.44 (s, 1 H), 7.40 (d,
J = 7.5 Hz, 1 H), 7.31–7.28 (m, 4 H), 7.23–7.20 (m, 1 H), 7.20–7.04
(m, 10 H), 6.81 (d, J = 7.9 Hz, 1 H), 6.67 (td, J = 7.6, 0.9 Hz, 1 H),
3.60 (s, 3 H) ppm. 13C NMR (100 MHz, CDCl3): δ = 158.1, 154.5, 149.6,
142.9, 142.3, 133.0, 130.4, 128.7, 128.2, 127.9, 126.8, 126.5, 125.8,
124.7, 124.6, 121.6, 119.6, 111.4, 70.2, 55.5 ppm. HRMS (EI): calcd.
for C28H22O [M]+ 374.1665; found 374.1668.
1-Isopropyl-2-{phenyl[2-(phenylethynyl)phenyl]methyl}-
benzene (3h): Yellow solid (254 mg, 66 %). m.p. 159–161 °C. 1H
NMR (400 MHz, CDCl3): δ = 7.60–7.51 (m, 1 H), 7.33–7.25 (m, 8 H),
7.25–7.17 (m, 4 H), 7.12–7.04 (m, 3 H), 6.94–6.87 (m, 1 H), 6.80 (dd,
J = 7.8, 1.3 Hz, 1 H), 6.36 (s, 1 H), 3.20–3.13 (m, 1 H), 1.08 (d, J =
6.8 Hz, 3 H), 0.94 (d, J = 6.8 Hz, 3 H) ppm. 13C NMR (100 MHz,
CDCl3): δ = 147.4, 145.8, 143.7, 140.3, 132.6, 131.6, 129.9, 129.8,
129.5, 128.3, 128.2, 128.2, 126.8, 126.3, 126.2, 125.7, 125.3, 123.4,
123.3, 94.1, 88.1, 50.99, 28.7, 24.4, 23.3 ppm. HRMS (EI): calcd. for
C30H26 [M]+ 386.2029; found 386.2027.
2-(3-Chlorophenyl)-1,1-diphenyl-1H-indene (2g): Colorless oil
(55 mg, 73 % yield). 1H NMR (400 MHz, CDCl3): δ = 7.40 (d, J =
7.4 Hz, 1 H), 7.37 (t, J = 1.8 Hz, 1 H), 7.31–7.26 (m, 4 H), 7.24–7.15
(m, 10 H), 7.13–7.08 (m, 2 H), 7.05 (t, J = 7.8 Hz, 1 H) ppm. 13C NMR
(100 MHz, CDCl3): δ = 155.5, 153.4, 141.7, 141.6, 137.3, 133.9, 130.1,
129.2, 128.6, 128.3, 127.8, 127.4, 127.2, 127.0, 126.6, 126.0, 124.6,
121.8, 68.8 ppm. HRMS (EI): calcd. for C27H19Cl [M]+ 378.1170; found
378.1173.
General Procedure for the Synthesis of 2a–2p: A solution of 1a
(69 mg, 0.2 mmol) and KOtBu (67 mg, 0.6 mmol) in DMF (2.0 mL)
was stirred under a nitrogen atmosphere for 1 h at room temp. The
reaction was then quenched with water (20 mL), and the mixture
was extracted with CH2Cl2 (2 × 15 mL). The combined organic
phases were dried with anhydrous Na2SO4, and filtered. The solvent
was removed under reduced pressure, and the residue was purified
2-(1,1-Diphenyl-1H-inden-2-yl)pyridine (2h): White solid (55 mg,
79 %). m.p. 151–153 °C. 1H NMR (400 MHz, CDCl3): δ = 8.58–8.47
(m, 1 H), 7.89 (s, 1 H), 7.47–7.45 (m, 1 H), 7.40–7.33 (m, 5 H), 7.26–
Eur. J. Org. Chem. 2016, 599–606
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