Oxidative Dearomatization of Phenols and Anilines via λ3- and λ5-Iodane-Mediated Phenylation and Oxygenation

Abstract

Treatment of 2-methylphenols with chloro(diphenyl)-λ3-iodane led to theirregioselective dearomatizing 2-phenylation into cyclohexa-2,4-dienone derivatives via aproposed ligand coupling reaction. In the same vein of investigation, treatment of2-methylanilines with the λ5-iodane 2-iodoxybenzoic acid IBX reagent led to theirregioselective dearomatization into previously undescribed ortho-quinol imines.

Keywords

• Iodanes
• phenols
• anilines
• dearomatization
• cyclohexadienones
• orthoquinol imines