Experimental study demonstrates enhanced stability, solubility, and oxidative reactivity of bidentate nitrogen-ligated iodine(V) reagents, suggesting a versatile platform for organic synthesis.
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.
No takes yet. Share an insight, caveat, or question.
Xiao et al. (2021) studied this question.
Synapse has enriched 5 closely related papers on similar clinical questions. Consider them for comparative context: