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LETTER
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The reaction was carried out in an autoclave containing a 10
mL Teflon reaction tube. Pd(PPh3)4 (0.02 mmol), DPPP
(0.04 mmol), and a magnetic stir bar were placed in the tube
which was then capped with a stopper and flushed with
argon. Then, aryl boronic acid (1 mmol), AgNO3 (1 mmol),
and acetone (3 mL) were added to the tube. The tube was put
into the autoclave. Once sealed, the autoclave was purged
several times with CO, pressurized to 1 atm at r.t. and then
heated in an oil bath at 40 °C for 24 h. The autoclave was
then cooled to r.t. and carefully vented to discharge CO in a
fume hood. Water (10 mL) was added, and the product was
extracted with CH2Cl2 (3 × 15 mL). The organic layers were
washed with brine, dried over Na2SO4, and evaporated. The
crude product was purified by column chromatography on
silica gel using a mixture of EtOAc and PE as eluent to give
the products. The identity and purity of the product was
confirmed by 1H NMR and 13C NMR spectroscopy and MS
or HRMS spectrometry.
Benzophenone (2a)
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Rf = 0.3 (PE–EtOAc, 50:1), yellow oil. 1H NMR (400 MHz,
CDCl3): δ = 7.83 (d, J = 7.6 Hz, 4 H), 7.62 (t, J = 7.2 Hz, 2
H), 7.51 (t, J = 7.6 Hz, 4 H) ppm. 13C NMR (100 MHz,
CDCl3): δ = 196.8, 137.6, 132.4, 130.1, 130.0, 128.3, 128.3
ppm. IR (KBr): 3040, 1658, 1603, 1321, 1274 cm–1. ESI-
HRMS: m/z calcd for [M + Na+]: 205.0621; found:
205.0624.
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Bis(4-fluorophenyl)meyhanone (2b)
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Rf = 0.3 (PE–EtOAc, 50:1), light yellow soild; mp 87–88 °C.
1H NMR (400 MHz, CDCl3): δ = 7.76–7.72 (m, 4 H), 7.11–
7.07 (m, 4 H) ppm. 13C NMR (100 MHz, CDCl3): δ = 193.7,
165.4 (d, JC–F = 252.9 Hz), 133.7 (d, JC–F = 3 Hz), 132.4 (d,
JC–F = 9.1 Hz), 115.5 (d, JC–F = 21.8 Hz) ppm. IR (KBr):
1647, 1496, 1295, 953, 760 cm–1. ESI-HRMS: m/z calcd for
[M + Na+]: 241.0442; found: 241.0435.
Bis(4-chlorophenyl)methanone (2c)
Rf = 0.3 (PE–EtOAc, 50:1), solid; mp 127–128 °C. 1H NMR
(400 MHz, CDCl3): δ = 7.72 (d, J = 8.4 Hz, 4 H), 7.46 (d,
J = 8.4 Hz, 4 H) ppm. 13C NMR (100 MHz, CDCl3): δ =
193.1, 138.1, 134.5, 130.3, 127.8 ppm. IR (KBr): 2364,
1651, 1585, 1275, 841, 756 cm–1. ESI-HRMS: m/z calcd for
[M + Na+]: 272.9851; found: 272.9844.
Synlett 2014, 25, 1097–1100
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