Azzena, Ugo Gavino and Cattari, Manuela and Melloni, Giovanni and Pisano, Luisa (2003) Reactivity of arylic carbanions generated by reductive cleavage of C-N bond of N,N-dimethylanilines. Synthesis, Vol. 2003 , p. 2811-2814. ISSN 0039-7881. eISSN 1437-210X. Article.
Phenyl-substituted N,N-dimethylanilines, synthesized by Suzuki coupling reactions in good yields, are transformed to their corresponding arylic carbanions by reductive C-N cleavage with lithium at room temperature. These carbanions react with various electrophiles affording the corresponding ipso-substituted products with absolute regioselectivity.