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

Citation

Xiao, X and Roth, JM and Greenwood, NS and Velopolcek, MK and Aguirre, J and Jalali, M and Ariafard, A and Wengryniuk, SE, Bidentate nitrogen-ligated I(V) reagents, Bi(N)-HVIs: preparation, stability, structure, and reactivity, Journal of Organic Chemistry, 86, (9) pp. 6566-6576. ISSN 0022-3263 (2021) [Refereed Article]


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DOI: doi:10.1021/acs.joc.1c00375

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 Details

Item Type:Refereed Article
Keywords:DFT calculations, hypervalent iodine chemistry, redox chemistry
Research Division:Chemical Sciences
Research Group:Physical chemistry
Research Field:Catalysis and mechanisms of reactions
Objective Division:Expanding Knowledge
Objective Group:Expanding knowledge
Objective Field:Expanding knowledge in the chemical sciences
UTAS Author:Jalali, M (Ms Mona Jalali)
UTAS Author:Ariafard, A (Associate Professor Alireza Ariafard)
ID Code:150050
Year Published:2021
Funding Support:Australian Research Council (DP180100904)
Web of Science® Times Cited:2
Deposited By:College Office - CoSE
Deposited On:2022-05-16
Last Modified:2022-05-18
Downloads:0

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