Open AccessBidentate Nitrogen-Ligated I(V) Reagents, Bi(N)-HVIs: Preparation, Stability, Structure, and Reactivity
Author(s) -
Xiao Xiao,
Jessica M. Roth,
Nathaniel S. Greenwood,
Maria K. Velopolcek,
Jordan C. Aguirre,
Mona Jalali,
Alireza Ariafard,
Sarah E. Wengryniuk
Publication year - 2021
Publication title -
journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.2
H-Index - 228
eISSN - 1520-6904
pISSN - 0022-3263
DOI - 10.1021/acs.joc.1c00375
Subject(s) - hypervalent molecule , chemistry , reagent , reactivity (psychology) , denticity , solubility , combinatorial chemistry , thermal stability , organic chemistry , organic synthesis , iodine , catalysis , crystal structure , medicine , alternative medicine , pathology
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.