Vicarious nucleophilic substitution

Vicarious nucleophilic substitution in organic chemistry is a special type of nucleophilic aromatic substitution in which a nucleophile replaces hydrogen and not an aromatic substituent like a halogen that is ordinarily encountered in this reaction type. This reaction type was introduce in 1987 by Mieczysław Mąkosza and Jerzy Winiarski. ["Vicarious nucleophilic substitution of hydrogen." Mieczysław Mąkosza and Jerzy Winiarski. Acc. Chem. Res.; 1987; 20(8) pp 282 - 289; DOI|10.1021/ar00140a003] ["Synthesis of heterocyclic compounds via vicarious nucleophilic substitution of hydrogen" Mieczysław Mąkosza Pure & Appl. Chem., Vol. 69, No. 3, pp. 559-564, 1997 [http://www.iupac.org/publications/pac/1997/pdf/6903x0559.pdf Article link] .]

It is typically encountered with nitroarenes and especially with carbon nucleophiles, resulting in new alkylated arenes. Carbon nucleophiles carry a electron-withdrawing group and a nucleofuge:

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