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Synthesis 2022; 54(20): 4481-4494
DOI: 10.1055/a-1883-1357
DOI: 10.1055/a-1883-1357
paper
Carbon Chain Rupture: Base-Induced Radical C–C Bond Cleavage of Alkylbenzimidazoles
This work was funded by the National Natural Science Foundation of China (Grant Nos. 21672159, 21871207).
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 oxidationSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1883-1357.
- Supporting Information
Publication History
Received: 03 April 2022
Accepted after revision: 23 June 2022
Accepted Manuscript online:
23 June 2022
Article published online:
27 July 2022
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