Cascade Approach to Highly Functionalized Biaryls by a Nucleophilic Aromatic Substitution with Arylhydroxylamines

Abstract

A transition-metal free synthesis of highly functionalized 2-hydroxy-2'-amino-1,1'-biaryls from N-arylhydroxylamines has been developed. This operationally simple and readily scalable approach relies on a cascade of reactions that initially generates transient N, O-diarylhydroxylamines, via direct O-arylation, which then undergo rapid [3,3]-sigmatropic rearrangement and subsequent rearomatization to form NOBIN-type products. These structurally diverse functionalized biaryls are obtained under mild conditions in good to excellent isolated yields.