Discovery of Periodinane Oxy-Assisted (POA) Oxidation Mechanism in the IBX-Controlled Oxidative Dearomatization of Pyrroles Mediated by Acetic Acid.

Kaveh FarshadfarNina GunawanFarshad ShiriJames K HowardAndaravaas Patabadige Jude P VaasAlex C Bissember Brian F Yates Jason A Smith Alireza Ariafard

Published in: The Journal of organic chemistry (2022)

The 2-iodoxybenzoic acid (IBX)-controlled oxidative dearomatization of pyrroles occurs very slowly (or not all) in many organic solvents, including DMSO in which IBX is soluble. Interestingly, although IBX is only partially soluble in acetic acid, this solvent mediates the pyrrole oxidative dearomatization. With the aid of density functional theory (DFT) calculations, we have discovered a new mode of reactivity, termed the periodinane oxy-assisted (POA) oxidation mechanism, which explains this observation.

Keyphrases

density functional theory
molecular dynamics
ionic liquid
hydrogen peroxide
small molecule
high throughput
molecular dynamics simulations