Reactivity of Hypervalent Iodine(III) Reagents Bearing Transferable N‐Based Groups

Electrophilic sources of nitrogen-based groups have been known for many decades and are of great synthetic importance. Hypervalent iodine reagents bearing N-containing groups have emerged as an alternative to classical electrophilic amination reactions, and are capable of transferring a wide diversity of nitrogen-containing functional groups to organic molecules. The reactivity of these reagents as well as the mechanism and scope of the reactions are reviewed.

Abstract

Hypervalent iodine reagents have the ability of inverting the polarity of functional groups bound to iodine, a reactivity known as umpolung. This reactivity makes hypervalent iodine compounds highly attractive for the creation of electrophilic synthons of known nucleophiles, resulting in novel synthetic disconnections and the formation of new Nu(nucleophile)−N bond.

Electrophilic sources of nitrogen-based groups have been known for many decades and are of great synthetic importance. Traditionally, these reagents are limited to few examples. With the use of hypervalent iodine, the transfer of a wide diversity of nitrogen sources became a possibility. This review compiles the latest reported examples of hypervalent iodine reagents capable of electrophilic transfer of nitrogen-based groups. It showcases the preparation of such reagents, their synthetic utility, and reaction mechanisms involving these group transfer reagents.

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