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Bidentate nitrogen-ligated I(V) reagents, Bi(N)-HVIs: preparation, stability, structure, and reactivity
journal contribution
posted on 2023-05-21, 07:39 authored by Xiao, X, Roth, JM, Greenwood, NS, Velopolcek, MK, Aguirre, J, Jalali, M, Alireza AriafardAlireza Ariafard, Wengryniuk, SEHypervalent 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.
Funding
Australian Research Council
University of Wollongong
History
Publication title
Journal of Organic ChemistryVolume
86Issue
9Pagination
6566-6576ISSN
0022-3263Department/School
School of Natural SciencesPublisher
Amer Chemical SocPlace of publication
1155 16Th St, Nw, Washington, USA, Dc, 20036Rights statement
© 2021 American Chemical SocietyRepository Status
- Restricted