Fluoroarenes aromatic nucleophilic substitution

Due to its strong activating effect in nucleophilic aromatic substitutions and to the possibility of its removal by decarbonylation, the aldehyde function has been used for the preparation of [ F]fluoroarenes not bearing electron-withdrawing substituents. Decarbonylations, possible in the presence of Pd/C [ 161 ], are more efficient in terms of time (15 min vs 1 h) and yields (80%) when using Wilkin-... 

Alkylation of Nitrile Derivatives. Tertiary benzylic nitriles were prepared from aryl fluorides and secondary nitrile anion. In the presence of 4 equiv of nitrile and 1.5 equiv of a base, the nucleophilic aromatic substitution of fluoroarenes led to tertiary benzylic nitriles (eq 36). KHMDS was the best base for this reaction, as LiHMDS and NaHMDS provided lower yields. The desired product was not observed when CS2CO3, LDA, or f-BuOK were used. "With KHMDS, the reaction proceeded in high yields with a variety of substrates. 

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