Synthesis, Characterization and Unusual Reactivity of Vinylbenziodoxolones-Novel Hypervalent Iodine Reagents.

Elin StridfeldtAlexandra SeemannMarinus J BoumaChandan DeyAnne ErtanBerit Olofsson

Published in: Chemistry (Weinheim an der Bergstrasse, Germany) (2016)

A novel type of hypervalent iodine(III) reagents, vinylbenziodoxolones (VBX), has been synthesized in a one-pot reaction from 2-iodobenzoic acid. VBX is bench stable, has been thoroughly characterized and the cyclic structure is supported by X-ray analysis. The reactivity of VBX was investigated in vinylation of nitrocyclohexane, and delivered vinylated products with opposite regioselectivity compared to acyclic vinyl(aryl)iodonium salts. The reagents could become a powerful tool in vinylation reactions under both metal-free and metal-catalyzed conditions.

Keyphrases

dual energy
computed tomography
high resolution
room temperature
ionic liquid
atomic force microscopy
magnetic resonance
contrast enhanced
data analysis
electron transfer