On April 30, 1992, Takagishi, Sadahito; Katsoulos, Georges; Schlosser, Manfred published an article.Formula: C12H14F3NO2 The title of the article was Fluorine and trifluoromethyl substituted anilines: site selective metalation and electrophilic substitution. And the article contained the following:
When treated with tert-butyllithium in THF at -50°, N-BOC (tert-butoxycarbonyl) protected fluoroanilines and trifluoromethylanilines, e.g., o-, m-, or p-F3CC6H4NHCO2CMe3, undergo metalation at the position adjacent to that carrying the nitrogen. 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. The experimental process involved the reaction of tert-Butyl (4-(trifluoromethyl)phenyl)carbamate(cas: 141940-37-6).Formula: C12H14F3NO2
The Article related to lithiation regioselective fluoroaniline, substituent effect lithiation fluoroaniline, Benzene, Its Derivatives, and Condensed Benzenoid Compounds: Carboxylic Acids and Peroxycarboxylic Acids and Their Sulfur-Containing Analogs and Salts and other aspects.Formula: C12H14F3NO2
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