Work

Iodine(III)-Catalyzed Oxidative Cyclization of Aryl Amines to Construct N -Alkylbenzimidazoles

Year: 2024

Type: article

Abstract: An I(III)-catalyzed oxidative cyclization reaction using selectfluor as the oxidant was developed that converts ortho -substituted anilines to benzimidazoles. The mild reaction requires as little as 0.5 mol % of iodobenzene, and its scope is broad: electron-withdrawing or electron-releasing groups on the aniline portion are tolerated, and cyclic or acyclic N -alkylamines are permitted as ortho -substituents. Preliminary mechanistic investigations suggest that benzimidazole formation occurs via cationic reactive intermediates, and an intramolecular kinetic isotope effect of 1.98 ± 0.05 was measured.

Source: The Journal of Organic Chemistry

DOI: 10.1021/acs.joc.4c00346

Authors: Carmen Margaret White, Sherlyn Cazares, Efren D. Gonzalez-Cortes, Tom G. Driver

Institution: University of Illinois Chicago

Language: English

Topic: Oxidative Organic Chemistry Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: National Institutes of Health, University of Illinois at Urbana-Champaign, National Institute of General Medical Sciences

Awards: G578814906, G9000291193