Iodonitrene: a direct metal-free electrophilic aminating reagent

Abstract

The use of conventional nitrenoids and/or metal nitrenes as electrophilic aminating reagents requires a pre-activated nitrogen atom, which makes transfer of an unprotected NH-group a difficult challenge. Iodonitrene, which is generated in situ from phenyliodine(III) diacetate and an ammonia surrogate, represents a new type of reactive electrophilic aminating reagent. The novel reactivity of iodonitrene not only resulted in direct NH-group transfer to nucleophilic atoms such as sulfur and nitrogen, but also led to the development of new reactions such as diazirine synthesis via decarboxylation and contractive synthesis of cyclobutanes via nitrogen extrusion. We highlight the contemporary advances in the application of iodonitrene and discuss the current limitations and future prospects.