Cross-coupling of arenediazonium tetrafluoroborates with arylboronic acids catalysed by palladium

Tetrahedron Letters

Volumn 37, Issue 22, 1996, Pages 3857-3860

  Darses, Sylvain ^a   Jeffery, Tuyet ^a   Genet, Jean Pierre ^a   Brayer, Jean Louis ^b   Demoute, Jean Pierre ^b  

^a CNRS   (France)

^b SANOFI   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUND; BORONIC ACID DERIVATIVE; DIAZONIUM COMPOUND; PALLADIUM;

ARTICLE; CHEMICAL REACTION; SYNTHESIS; TEMPERATURE;

LATEOLABRAX JAPONICUS;

EID: 0030014134     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00699-5     Document Type: Article

References (26)

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5. For palladium-catalysed reactions in aqueous medium see : a) Genet, J. P.; Lindquist, A.; Blart, E.; Mouries, V.; Savignac, M.; Vaultier, M. Tetrahedron Lett. 1995, 36, 1443-1446.
6. b) Genet, J. P.; Blart, E.; Savignac, M. Synlett 1992, 715-717.
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20. Kikukawa, K.; Kono, K.; Nagira, K.; Wada, F.; Matsuda, T. J. Org. Chem. 1981, 46, 4413-4416.
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23. Arenediazonium tetrafluoroborates are prepared according to Roe, A. Organic Reactions 1949, 5, 193-228 and are purified, several times if necessary, by precipitation of the filtered solution of reagent grade acetone by the addition of diethyl ether. The salts can be stored under an argon atmosphere at -20°C for several months.
24. Use of arenediazonium hexafluorophosphate instead of arenediazonium tetrafluoroborate, affords only small amounts of the expected cross-coupling product.
25. Arylboronic esters are not reactive under the conditions described.
26. 2 were placed in a flask under an argon atmosphere, in the dark. Then, 2 ml of anhydrous and degassed 1,4-dioxane were added and the resulted suspension was stirred at 20°C. The course of the coupling was followed by measuring gas evolution with a gas buret. After completion of the gas evolution, the catalyst was filtered off and washed with diethyl ether. The organic phase was washed with saturated sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was removed and the crude product was purified by chromatography on silica gel.