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Discovery of Periodinane Oxy-Assisted (POA) oxidation mechanism in the IBX-Controlled oxidative dearomatization of pyrroles mediated by acetic acid
journal contribution
posted on 2023-05-21, 14:15 authored by Farshadfar, K, Nina GunawanNina Gunawan, Shiri, F, Howard, JK, Andaravaas Patabadige Jude VaasAndaravaas Patabadige Jude Vaas, Alexander BissemberAlexander Bissember, Brian YatesBrian Yates, Jason SmithJason Smith, Alireza AriafardAlireza AriafardThe 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.
Funding
Australian Research Council
History
Publication title
The Journal of Organic ChemistryVolume
87Pagination
13280–13287ISSN
0022-3263Department/School
School of Natural SciencesPublisher
Amer Chemical SocPlace of publication
1155 16Th St, Nw, Washington, USA, Dc, 20036Rights statement
© 2022 American Chemical Society.Repository Status
- Restricted