Reactivity of Arylic Carbanions Generated by Reductive Cleavage of C-N Bond of N,N-Dimethylanilines

Ugo Azzena; Manuela Cattari; Giovanni Melloni; Luisa Pisano

doi:10.1055/s-2003-42481

PAPER

Reactivity of Arylic Carbanions Generated by Reductive Cleavage of C-N Bond of N,N-Dimethylanilines

Ugo Azzena, Manuela Cattari, Giovanni Melloni, Luisa Pisano*
Dipartimento di Chimica, Università di Sassari, via Vienna 2, 07100 Sassari, Italy
Fax: +39(079)229559; e-Mail: luisa@uniss.it;

Abstract

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Abstract

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.

Key words

aryllithium - reduction - regioselectivity - deamination - terphenyls

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References

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