Carbon Chain Rupture: Base-Induced Radical C–C Bond Cleavage of Alkylbenzimidazoles

Abstract

A base-mediated aerobic oxidation of alkylbenzimidazoles for the preparation of carboxylic acids is described. A number of aliphatic carboxylic acids have been prepared in good to excellent yields via a C–C bond rupture process. Preliminary mechanistic studies suggest the reaction undergoes a radical pathway initiated by strong bases such as potassium amide. This type of transformation provides an alternative strategy for the access of important carboxylic acid moieties.

Key words

C–C cleavage - radical generation - heterocycles - potassium hexamethyldisilazide - aerobic oxidation

Publikationsverlauf

Eingereicht: 03. April 2022

Angenommen nach Revision: 23. Juni 2022

Accepted Manuscript online:
23. Juni 2022

Artikel online veröffentlicht:
27. Juli 2022

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