Efficient oxidative ipso-fluorination of para-substituted phenols using pyridinium polyhydrogen fluoride in combination with hypervalent iodine(III) reagents

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-...

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Bibliographic Details
Published in:Tetrahedron 2004-07, Vol.60 (31), p.6629-6638
Main Authors: Karam, Omar, Martin-Mingot, Agnès, Jouannetaud, Marie-Paule, Jacquesy, Jean-Claude, Cousson, Alain
Format: Article
Language:English
Subjects:
Fluorodienone
Hypervalent iodine
Ipsofluorination
Pyridinium polyhydrogen fluoride
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Summary: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. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2004.05.083