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

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.

Funding

Australian Research Council

History

Publication title

The Journal of Organic Chemistry

Volume

87

Pagination

13280–13287

ISSN

0022-3263

Department/School

School of Natural Sciences

Publisher

Amer Chemical Soc

Place of publication

1155 16Th St, Nw, Washington, USA, Dc, 20036

Rights statement

© 2022 American Chemical Society.

Repository Status

  • Restricted

Socio-economic Objectives

Expanding knowledge in the chemical sciences

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