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Discovery of Periodinane Oxy-Assisted (POA) oxidation mechanism in the IBX-Controlled oxidative dearomatization of pyrroles mediated by acetic acid

Citation

Farshadfar, K and Gunawan, N and Shiri, F and Howard, JK and Vaas, APJP and Bissember, AC and Yates, BF and Smith, JA and Ariafard, A, Discovery of Periodinane Oxy-Assisted (POA) oxidation mechanism in the IBX-Controlled oxidative dearomatization of pyrroles mediated by acetic acid, The Journal of Organic Chemistry, 87 pp. 13280-13287. ISSN 0022-3263 (2022) [Refereed Article]

Copyright Statement

2022 American Chemical Society.

DOI: doi:10.1021/acs.joc.2c01923

Abstract

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.

Item Details

Item Type:Refereed Article
Keywords:hypervalent iodine, DFT, reaction mechanism, pyrrole
Research Division:Chemical Sciences
Research Group:Organic chemistry
Research Field:Organic chemical synthesis
Objective Division:Expanding Knowledge
Objective Group:Expanding knowledge
Objective Field:Expanding knowledge in the chemical sciences
UTAS Author:Gunawan, N (Miss Nina Gunawan)
UTAS Author:Howard, JK (Mr James Howard)
UTAS Author:Vaas, APJP (Mr Andaravaas Patabadige Jude Vaas)
UTAS Author:Bissember, AC (Associate Professor Alex Bissember)
UTAS Author:Yates, BF (Professor Brian Yates)
UTAS Author:Smith, JA (Professor Jason Smith)
UTAS Author:Ariafard, A (Associate Professor Alireza Ariafard)
ID Code:153826
Year Published:2022
Funding Support:Australian Research Council (FT200100049)
Deposited By:Chemistry
Deposited On:2022-10-09
Last Modified:2022-11-01
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