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Synlett 1992; 1992(4): 360-362
DOI: 10.1055/s-1992-22015
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Fluorine and Trifluoromethyl Substituted Anilines: Site Selective Metalation and Electrophilic Substitution

Sadahito Takagishi* , Georges Katsoulos, Manfred Schlosser
  • *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 tert-butyllithium in tetrahydrofuran at -50 °C, N-BOC (tert-butoxycarbonyt) protected fluoroanilines and trifluoromethylanilines undergo metalation at the nitrogenadjacent position. If, however, the nitrogen carries two alkyl or trimethylsilyl groups as substituents and highly polar metalating reagents such as butyllithium activated by N,N,N′N″,N″-pentamethyldiethylenetriamine (PMDTA) or potassium tert-butoxide are employed, the fluoroaniline derivatives are preferentially deprotonated next to the halogen atom.