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Xiao X , Roth JM , Greenwood NS , Velopolcek MK , Aguirre J , Jalali M , Ariafard A , Wengryniuk SE
Bidentate Nitrogen-Ligated I(V) Reagents, Bi(N)-HVIs: Preparation, Stability, Structure, and Reactivity
J Org Chem. 2021 May 7;86(9) :6566-6576
AbstractHypervalent 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.
Notes1520-6904 Xiao, Xiao Roth, Jessica M Greenwood, Nathaniel S Velopolcek, Maria K Aguirre, Jordan Jalali, Mona Ariafard, Alireza Wengryniuk, Sarah E Orcid: 0000-0002-4797-0181 Journal Article United States J Org Chem. 2021 May 7;86(9):6566-6576. doi: 10.1021/acs.joc.1c00375. Epub 2021 Apr 19.