Alkylation of Nitroaromatics with Trialkylborane

Abstract

A novel, facile, aromatic substitution reaction of nitroaromatics is described. When p-dinitrobenzene (1) is treated with trialkylborane in the presence of potassium tert-butoxide, it furnishes p-alkylnitrobenzene (2) in high yield. A tentative mechanism is suggested involving alkyl radicals and radical anions of the nitroaromatic substrate.