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

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

References

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  Melloni, G.; Pisano, L. unpublished results

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17

N,N-Dimethylaniline was not reductively cleaved under our reaction conditions. See ref. [5]