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Synlett 2014; 25(08): 1097-1100
DOI: 10.1055/s-0033-1340957
DOI: 10.1055/s-0033-1340957
letter
Palladium-Catalyzed Oxidative Carbonylation for the Synthesis of Symmetrical Diaryl Ketones at Atmospheric CO Pressure
Weitere Informationen
Publikationsverlauf
Received: 20. Januar 2014
Accepted after revision: 18. Februar 2014
Publikationsdatum:
24. März 2014 (online)
![](https://www.thieme-connect.de/media/synlett/201408/lookinside/thumbnails/10.1055-s-0033-1340957-1.jpg)
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.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
- Supporting Information
-
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) 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. Bis(4-fluorophenyl)meyhanone (2b) 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, 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) 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.
For reviews, see:
For selected examples of palladium-catalyzed carbonylations of aryl halides, see:
For recent examples, see:
For recent examples, see:
For recent examples, see:
For recent examples, see: