TY - JOUR
T1 - Bidentate Nitrogen-Ligated I(V) Reagents, Bi(N)-HVIs
T2 - Preparation, Stability, Structure, and Reactivity
AU - Xiao, Xiao
AU - Roth, Jessica M.
AU - Greenwood, Nathaniel S.
AU - Velopolcek, Maria K.
AU - Aguirre, Jordan
AU - Jalali, Mona
AU - Ariafard, Alireza
AU - Wengryniuk, Sarah E.
N1 - © 2021 The Author(s)
PY - 2021/5/7
Y1 - 2021/5/7
N2 - 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.
AB - 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.
UR - https://www.scopus.com/pages/publications/85105086851
U2 - 10.1021/acs.joc.1c00375
DO - 10.1021/acs.joc.1c00375
M3 - Article
AN - SCOPUS:85105086851
SN - 0022-3263
VL - 86
SP - 6566
EP - 6576
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 9
ER -