Tetrahedron

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

…, A Martin-Mingot, MP Jouannetaud, JC Jacquesy…

Index: Karam, Omar; Martin-Mingot, Agnes; Jouannetaud, Marie-Paule; Jacquesy, Jean-Claude; Cousson, Alain Tetrahedron, 2004 , vol. 60, # 31 p. 6629 - 6638

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Citation Number: 18

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 ...