Efficient oxidative ipso-fluorination of para-substituted phenols using pyridinium polyhydrogen fluoride in combination with hypervalent iodine(III) reagents |
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Authors: | Omar Karam Agnès Martin-Mingot Jean-Claude Jacquesy |
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Institution: | a Laboratoire ‘Synthèse et Réactivité des Substances Naturelles’, UMR 6514, 40, Avenue du Recteur Pineau, F-86022 Poitiers Cedex, France b Laboratoire Léon Brillouin - CEA Saclay, 91191 Gif-sur-Yvette Cedex, France |
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Abstract: | Diacetoxyiodobenzene (PIDA) and bis(trifluoroacetoxy)iodobenzene (PIFA) in the presence of pyridinium polyhydrogen fluoride (PPHF) are effective for the fluorination of para-substituted phenols to give a variety of 4-fluorocyclohexa-2,5-dienones in a good yield. (R,S)-1,1′-Bi-5,6,7,8-tetrahydro-2-naphthol (and its monoacetate) yields atropoisomeric fluorocyclohexadienones. The 4-substituted carbamate open-chain phenols were readily converted to fluorohydroindolenone and fluorohydroquinolenone derivatives by intramolecular conjugate addition. |
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Keywords: | Ipsofluorination Pyridinium polyhydrogen fluoride Hypervalent iodine Fluorodienone |
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