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

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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. This strategy results in novel synthetic disconnections and the creation 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.
Original languageEnglish
Article numbere202300109
Number of pages26
JournalEuropean Journal of Organic Chemistry
Issue number25
Early online date30 Apr 2023
Publication statusPublished - 3 Jul 2023


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