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Bidentate nitrogen-ligated I(V) reagents, Bi(N)-HVIs: preparation, stability, structure, and reactivity

Xiao, X, Roth, JM, Greenwood, NS, Velopolcek, MK, Aguirre, J, Jalali, M, Ariafard, A ORCID: 0000-0003-2383-6380 and Wengryniuk, SE 2021 , 'Bidentate nitrogen-ligated I(V) reagents, Bi(N)-HVIs: preparation, stability, structure, and reactivity' , Journal of Organic Chemistry, vol. 86, no. 9 , pp. 6566-6576 , doi: 10.1021/acs.joc.1c00375.

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Abstract

Hypervalent iodine(V) reagents are a powerful class of organic oxidants. While the use of I(V) compounds Dess-Martin periodinane and IBX is widespread, this reagent class has long been plagued by issues of solubility and stability. Extensive effort has been made for derivatizing these scaffolds to modulate reactivity and physical properties but considerable room for innovation still exists. Herein, we describe the preparation, thermal stability, optimized geometries, and synthetic utility of an emerging class of I(V) reagents, Bi(N)-HVIs, possessing datively bound bidentate nitrogen ligands on the iodine center. Bi(N)-HVIs display favorable safety profiles, improved solubility, and comparable to superior oxidative reactivity relative to common I(V) reagents. The highly modular synthesis and in situ generation of Bi(N)-HVIs provides a novel and convenient screening platform for I(V) reagent and reaction development.

Item Type: Article
Authors/Creators:Xiao, X and Roth, JM and Greenwood, NS and Velopolcek, MK and Aguirre, J and Jalali, M and Ariafard, A and Wengryniuk, SE
Keywords: DFT calculations, hypervalent iodine chemistry, redox chemistry
Journal or Publication Title: Journal of Organic Chemistry
Publisher: Amer Chemical Soc
ISSN: 0022-3263
DOI / ID Number: 10.1021/acs.joc.1c00375
Copyright Information:

© 2021 American Chemical Society

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