Iodonitrene: a direct metal-free electrophilic aminating reagent

Hui, C. and Antonchick, A.P. ORCID: 0000-0003-0435-9443, 2022. Iodonitrene: a direct metal-free electrophilic aminating reagent. Organic Chemistry Frontiers. ISSN 2052-4110

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Abstract

The use of conventional nitrenoids and/or metal–nitrenes as electrophilic aminating reagents requivuires a pre-activated nitrogen atom which makes transfer of an unprotected NH–group a difficult challenge. Iodonitrene, which is generated in-situ from (diacetoxyiodo)benzene and ammonia surrogate, features a new class of reactive electrophilic aminating reagents. 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 new reaction development such as diazirines 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.

Item Type: Journal article
Publication Title: Organic Chemistry Frontiers
Creators: Hui, C. and Antonchick, A.P.
Publisher: Royal Society of Chemistry
Date: 14 June 2022
ISSN: 2052-4110
Identifiers:
NumberType
10.1039/d2qo00739hDOI
1557386Other
Divisions: Schools > School of Science and Technology
Record created by: Jonathan Gallacher
Date Added: 28 Jun 2022 08:30
Last Modified: 28 Jun 2022 08:30
URI: http://irep.ntu.ac.uk/id/eprint/46486

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