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

Autor:	Kaveh Farshadfar, Nina Gunawan, Farshad Shiri, James K. Howard, Andaravaas Patabadige Jude P. Vaas, Alex C. Bissember, Brian F. Yates, Jason A. Smith, Alireza Ariafard
Přispěvatelé:	Department of Chemistry and Materials Science, University of Tasmania, Islamic Azad University, Aalto-yliopisto, Aalto University
Rok vydání:	2022
Předmět:	Oxidative Stress Organic Chemistry Solvents Dimethyl Sulfoxide Pyrroles Acetic Acid
Zdroj:	The Journal of Organic Chemistry. 87:13280-13287
ISSN:	1520-6904 0022-3263
DOI:	10.1021/acs.joc.2c01923
Popis:	Publisher Copyright: © 2022 American Chemical Society. 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.
Databáze:	OpenAIRE
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