Rhodium-Catalyzed Regioselective Diarylation of Antiaromatic Ni(II) Norcorroles

Abstract The rhodium-catalyzed arylation of antiaromatic Ni(II) norcorrole with aryl boronic acids was investigated. Treatment of Ni(II) dimesitylnorcorrole with phenylboronic acid in the presence of K3PO4 and a [RhCl(cod)]2/rac-BINAP catalyst combination efficiently provided an isomeric mixture of cis- and trans-diphenylation products. The two phenyl substituents were introduced with perfect regioselectivity at positions C3 and C13 of the norcorrole skeleton. Diphenylation substantially altered the optical and electrochemical properties as well as the antiaromaticity of Ni(II) norcorrole.