Hypervalent Iodine(III)-Mediated Oxidative Dearomatizing Cyclization of Arylamines

An oxidative dearomatizing cyclization of arylamines promoted by iodobenzene bis(trifluoroacetate) [PhI(CF3CO2)(2)] has been explored, leading to a novel synthetic approach to functionalized spirocyclic building blocks containing the structurally unique dieniminium moiety. This unprecedented methodology, featuring oxidative dearomatization and carbon-carbon bond-forming cyclization, to some extent, not only expands the synthetic potential of hypervalent iodine chemistry, but also enriches the oxidation chemistry of arylamines.