Superbase Reactions: The Expedient and Selective Metalation of Fluorine- or  Trifluoromethyl-Substituted Benzenes

Manfred Schlosser; Georges Katsoulos; Sadahito Takagishi

doi:10.1055/s-1990-21236

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Synlett 1990; 1990(12): 747-748
DOI: 10.1055/s-1990-21236

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Superbase Reactions: The Expedient and Selective Metalation of Fluorine- or Trifluoromethyl-Substituted Benzenes

Manfred Schlosser^* , Georges Katsoulos, Sadahito Takagishi

^*Institut de Chimie organique de l'Université, Rue de la Barre 2, CH-1005 Lausanne, Switzerland

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Publication Date:
08 March 2002 (online)

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When treated with the superbasic mixture of butyllithium and potassium tert-butoxide, fluorobenzene, difluorobenzenes, fluoro(trifluoromethyl)benzenes, (trifluoromethyl)benzene and bis(trifluoromethyl)benzenes undergo site selective hydrogen-metal exchange. Best results are obtained in tetrahydrofuran solutions at -75 °C or -50 °C. Upon quenching with carbon dioxide the corresponding carboxylic acids are obtained in good to excellent yield.