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Reactivity of Para-Substituted Fluorobenzenes in Palladium-catalyzed Intermolecular Direct Arylations

Abstract : The influence of both electron-withdrawing and electron-donating substituents such as amino, bromo, chloro, ketone, methyl, methoxy, and nitro at C-4 on fluorobenzene derivatives, for palladium-catalyzed direct arylation at α-position to the fluorine atom has been explored. With moderate electron-withdrawing substituents, the reaction proceeds nicely using phosphine-free PdCl2 catalyst, at a very low loading, and potassium pivalate/dimethylacetamide (PivOK/DMA) as catalytic system. In all cases, a regioselective arylation at the α position to the fluorine atom was observed. Moreover, a wide variety of substituents on the aryl bromide coupling partner, such as formyl, nitro, nitrile, chloro, and methyl, and also heteroaryl bromides was tolerated
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https://hal-univ-rennes1.archives-ouvertes.fr/hal-01196567
Contributor : Laurent Jonchère <>
Submitted on : Thursday, September 10, 2015 - 10:00:01 AM
Last modification on : Friday, July 10, 2020 - 4:02:58 PM

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Mian He, Jean-François Soulé, Henri Doucet. Reactivity of Para-Substituted Fluorobenzenes in Palladium-catalyzed Intermolecular Direct Arylations. ChemCatChem, Wiley, 2015, 7 (14), pp.2130--2140. ⟨10.1002/cctc.201500185⟩. ⟨hal-01196567⟩

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