Direct Construction of NOBINs via Domino Arylation and Sigmatropic Rearrangement Reactions

Privileged 2-amino-2'-hydroxy-1,1'-binaphthyl (NOBIN) frameworks were constructed through a novel domino arylation of naphthylhydroxylamines with diarylhalonium salts and sigmatropic rearrangement in a transition metal-free fashion. This protocol bears broad substrate generality and proceeds under mild reaction conditions, affording diversified NOBINs in high efficiency with absolute regiocontrol during the rearrangement process. Optically active product was accessible by chiralN-heterocyclic carbene-catalyzed kinetic resolution in one pot or diastereoselective [3,3]-rearrangement guided by a removable chiral auxiliary. Remarkably, diarylchloronium and diarylbrominium salts have been employed as arylation reagents for the first time in assembling such representative biaryl frameworks.