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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 |
| Downloads: | 0 |
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