Palladium-Catalyzed Oxidative Carbonylation for the Synthesis of Symmetrical Diaryl Ketones at Atmospheric CO Pressure

Abstract

A mild and efficient synthesis of symmetrical diaryl ketones by palladium-catalyzed oxidative carbonylation of arylboronic acids with carbon monoxide at atmospheric pressure is reported.

Key words

palladium - carbonylation - carbon monoxide - aryl­boronic acids - diaryl ketone

• References and Notes


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• 22 General Procedure for the Carbonylation of Arylboronic Acids 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) R_f  = 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. Bis(4-fluorophenyl)meyhanone (2b) R_f  = 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, J _C–F = 252.9 Hz), 133.7 (d, J _C–F = 3 Hz), 132.4 (d, J _C–F = 9.1 Hz), 115.5 (d, J _C–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) R_f  = 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.