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14 3-Arylindan-1-ones have been synthesized
from 3-bromo-indenone and pinacol boronate esters, which have to
be prepared from the corresponding boronic acids: Clark WM.
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16 The reaction was performed on 5-10g
of indanone.
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18
Typical Experiment
for the Suzuki Reaction: A solution of the β-bromoindenone 3 (4.18 g, 20 mmol) and 3,4-dichlorophenyl-boronic
acid (4.2 g, 22 mmol) in THF (100 mL) containing absolute EtOH (20
mL) and H2O (20 mL) was degased with argon for 20 min.
Na2CO3 (6.36 g, 60 mmol) and Pd(PPh3)4 (1.16
g, 1 mmol) were added to this solution. The resulting mixture was
vigourously stirred at r.t. for 1.5 d under an argon atmosphere
and then diluted with CH2Cl2 (250 mL). The
reaction mixture was washed with H2O (2 × 100
mL) and the aqueous layer extracted with CH2Cl2 (100
mL). The combined organic layers were dried over MgSO4 and
filtered. The solvent was removed in vacuo and the residue was purified
by flash column chromatography on silica gel (60/40 petroleum
ether/CH2Cl2) to give the β-arylindenone 4 as a yellow solid (4.95 g, 90% yield):
Mp 148-150 °C. IR: 1700 cm-1. 1H
NMR (CDCl3): δ = 7.74 (d, J = 2.0
Hz, 1 H), 7.63-7.25 (6 H), 6.01 (s, 1 H). 13C
NMR (CDCl3): δ = 121.2 (CH), 123.1
(CH), 123.9 (CH), 126.6 (CH), 129.1 (CH), 129.6 (CH), 131.1 (CH),
131.9 (C), 132.9 (C), 133.1 (CH), 133.4 (C), 134.6 (C), 143.3 (C),
160.1 (C), 196.3 (C). MS (EI): m/z
(rel. int.) = 274
(86) [M+], 239 (100), 211
(28), 176 (73).
19
Rylander PN.
Catalytic Hydrogenation in Organic Syntheses
Academic
Press;
New York:
1979.
p.114
20
Jourdant A.
Gonzalez-Zamora E.
Zhu J.
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2002,
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21
Typical Experiment
for the Wilkinson Hydrogenation: (PPh3)3RhCl
(0.122 g, 0.132 mmol) was added to a solution of β-arylindenone 4 (0.91 g, 3.3 mmol) in THF/t-BuOH
(1/1, 24 mL)
under an argon atmosphere. The resulting solution was saturated
with hydrogen and stirred under one atmosphere of hydrogen overnight
at r.t. The reaction mixture was filtered through a short pad of
alumina and washed thoroughly with EtOAc. The solvent was removed
in vacuo and the residue was purified by flash column chromatography
on silica gel (90/10 petroleum ether/EtOAc) to
provide β-arylindenone 5 as a
colorless solid (0.74 g, 81% yield): Mp 113-115 °C.
IR: 1710 cm-1.
1H
NMR (CDCl3): δ = 7.82 (d, J = 7.7
Hz, 1 H), 7.61 (td, J = 7.5, 1.2 Hz, 1 H),
7.45 (t, J = 7.4
Hz, 1 H), 7.38 (d, J = 8.3 Hz, 1 H), 7.30-7.20
(2 H), 6.96 (dd, J = 8.3, 2.1 Hz, 1 H),
4.55 (dd, J = 8.1,
3.8 Hz, 1 H), 3.23 (dd, J = 19.2,
8.1 Hz, 1 H), 2.62 (dd, J = 19.2, 3.8 Hz, 1 H). 13C
NMR (CDCl3): δ = 204.8 (C), 156.4 (C),
143.9 (C), 136.7 (C), 135.3 (CH), 132.9 (C), 131.1 (C), 130.9 (CH),
129.6 (CH), 128.3 (CH), 126.9 (CH), 126.6 (CH), 123.6 (CH), 46.4 (CH2),
43.5 (CH). MS (EI): m/z (rel.
int.) = 276 (100) [M+], 241
(77), 212 (25), 178 (60).
22 Separated by flash chromatography
on silica gel (70/30 petroleum ether/EtOAc).
23
Compound 8a: Mp
116-118 °C. IR 1710 cm-1. 1H
NMR (CDCl3): δ = 7.81 (d, J = 7.6 Hz,
1 H), 7.59 (td, J = 7.5,
1.1 Hz, 1 H), 7.43 (t, J = 7.4
Hz, 1 H), 7.25 (dd, J = 7.6,
0.8 Hz, 1 H), 7.14-6.93 (4 H), 4.57 (dd, J = 8.0,
3.8 Hz, 1 H), 3.23 (dd, J = 19.3,
8.1 Hz, 1 H), 2.64 (dd, J = 19.3,
3.9 Hz, 1 H). 13C NMR (CDCl3): δ = 205.5
(C), 161.8 (d, J = 245 Hz, CF), 157.6
(C), 139.4 (C), 136.7 (C), 135.1 (CH), 129.1 (CH), 129.0 (CH), 128.0
(CH), 126.7 (CH), 123.4 (CH), 115.9 (CH), 115.6 (CH), 46.9 (CH2),
43.7 (CH). MS (EI):
m/z (rel.
int.) = 226 (100) [M+],
197 (30), 183 (28).
24
Compound 8b: Mp
108-110 °C. IR: 2230, 1710 cm-1. 1H NMR
(CDCl3): δ = 7.83 (d, J = 7.7
Hz, 1 H), 7.67-7.56 (3 H), 7.47 (t, J = 7.5
Hz, 1 H), 7.30-7.20 (3 H), 4.67 (dd, J = 8.1,
3.8 Hz, 1 H), 3.27 (dd, J = 19.2,
8.2 Hz, 1 H), 2.64 (dd, J = 19.2,
3.8 Hz, 1 H). 13C NMR (CDCl3): δ = 204.5
(C), 156.2 (C), 149.1 (C), 136.7 (C), 135.3 (CH), 132.7 (2 CH), 128.4
(3 CH), 126.6 (CH), 123.7 (CH), 118.5 (C), 111.0 (C), 46.2 (CH2),
44.3 (CH). MS (EI) m/z (rel.
int.) = 233 (100) [M+],
204 (30), 190 (22).
