Oxidative nucleophilic alkoxylation of nitrobenzenes

Abstract

Oxidative nucleophilic aromatic substitution of hydrogen in nitroaromatics with potassium alkoxides derived from primary, secondary or tertiary alcohols in the presence of oxygen was achieved. Mechanistic investigations suggest the formation of a deprotonated σ_H adduct. The products showed good reactivity in nucleophilic aromatic substitution of the nitro group with oxygen or nitrogen nucleophiles to access selectively substituted aromatic compounds.