Direct arylation of nitrobenzenes and of heterocycles via an oxygen analogue of the benzidine rearrangement

Abstract

Benzyl N-hydroxy-N-phenylcarbamate (1) and N-phenylbenzohydroxamic acid (10) react with active halogenobenzenes to give derivatives of 4-amino-4′-hydroxybiphenyl. The reactions of compound (1) or (10) with certain 2-chloro-pyridines, -pyrimidines, and -pyrazines result in introduction of the 4-aminophenyl group at position 5 of the heterocycle. The scope and limitations of the reaction are discussed.