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Synlett 1991; 1991(10): 731-732
DOI: 10.1055/s-1991-34754
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The Metalation of Fluoroanisoles: Optional Regioselectivity Due to Metal Mediated Control

Georges Katsoulos* , Sadahito Takagishi, Manfred Schlosser
  • *Institut de Chimie organique de l'Université, Rue de la Barre 2, CH-1005 Lausanne, Switzerland
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Publication History

Publication Date:
13 March 2002 (online)

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2- and 4-Fluoroanisole undergo hydrogen/metal exchange at the position next to the alkoxy moiety if butyllithium or tert-butyllithium is employed and at the position next to the halogen atom if the stoichiometric mixture of butyllithium and potassium tert-butoxide serves as the reagent. 3-Fluoroanisole is always attacked at the position flanked by the two heterosubstituents.