Fluorine and trifluoromethyl substituted anilines: site selective metalation and electrophilic substitution

When treated with tert-butyllithium in THF at -50 Deg, 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 derivs. are preferentially deprotonated next to the halogen atom. [on SciFinder (R)]


Published in:
Synlett, 4, 360-2
Year:
1992
Keywords:
Note:
CAN 117:7608
25-17
Benzene, Its Derivatives, and Condensed Benzenoid Compounds
Inst. Chim. Org.,Univ. Lausanne,Lausanne,Switz.
Journal
0936-5214
written in English.
403-46-3; 60144-53-8; 81740-18-3; 98968-72-0; 109134-07-8; 141940-36-5; 141940-37-6; 141940-38-7; 141940-39-8 Role: RCT (Reactant), RACT (Reactant or reagent) (lithiation of, regioselectivity in); 446-31-1P; 141940-27-4P; 141940-28-5P; 141940-29-6P; 141940-30-9P; 141940-31-0P; 141940-32-1P; 141940-33-2P; 141940-34-3P; 141940-35-4P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of)
Laboratories:




 Record created 2006-03-03, last modified 2018-01-27


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