Hypervalent-Iodine(III)-Mediated Tandem Oxidative Dearomatization/Aziridination of Phenolic Amines: Synthesis of Functionalized Unactivated Aziridines

Chemistry. 2021 Jun 10;27(33):8473-8478. doi: 10.1002/chem.202100762. Epub 2021 May 11.

Abstract

A new hypervalent-iodine(III)-mediated tandem reaction involving oxidative dearomatization and in situ aziridination of phenolic amines is described, providing a mild and effective method for the assembly of structurally interesting and synthetically useful aziridines. Importantly, the densely functionalized aziridines resulting from this unprecedented tandem reaction offer a platform for expeditious access to architecturally diverse aza-heterocycles through transformations initiated by selective ring-opening of aziridines.

Keywords: Aziridines; cascade reactions; dearomatization; iodine; oxidation.