Synthesis, Table of Contents

Synthesis 2022; 54(20): 4481-4494
DOI: 10.1055/a-1883-1357

paper

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

Xuegang Fu

^aSchool of Pharmaceutical Science and Technology, Tianjin University, 92 Weijin Road, Nankai District, Tianjin 300072, P. R. of China

^bCollaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300072, P. R. of China

^cTianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, P. R. of China

,

Dongyang Guo

^aSchool of Pharmaceutical Science and Technology, Tianjin University, 92 Weijin Road, Nankai District, Tianjin 300072, P. R. of China

^bCollaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300072, P. R. of China

^cTianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, P. R. of China

,

Yuting Yan

^aSchool of Pharmaceutical Science and Technology, Tianjin University, 92 Weijin Road, Nankai District, Tianjin 300072, P. R. of China

^bCollaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300072, P. R. of China

^cTianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, P. R. of China

,

Timotius Marselo

^aSchool of Pharmaceutical Science and Technology, Tianjin University, 92 Weijin Road, Nankai District, Tianjin 300072, P. R. of China

^bCollaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300072, P. R. of China

^cTianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, P. R. of China

,

Mingyu Zhang

^aSchool of Pharmaceutical Science and Technology, Tianjin University, 92 Weijin Road, Nankai District, Tianjin 300072, P. R. of China

^bCollaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300072, P. R. of China

^cTianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, P. R. of China

,

Zhenghan Zhang

^aSchool of Pharmaceutical Science and Technology, Tianjin University, 92 Weijin Road, Nankai District, Tianjin 300072, P. R. of China

^bCollaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300072, P. R. of China

^cTianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, P. R. of China

,

Siying Li

^aSchool of Pharmaceutical Science and Technology, Tianjin University, 92 Weijin Road, Nankai District, Tianjin 300072, P. R. of China

^bCollaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300072, P. R. of China

^cTianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, P. R. of China

,

Jianhui Huang∗

^aSchool of Pharmaceutical Science and Technology, Tianjin University, 92 Weijin Road, Nankai District, Tianjin 300072, P. R. of China

^bCollaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300072, P. R. of China

^cTianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, P. R. of China

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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

Key words

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

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Supplementary Material

Supplementary Material

Supporting Information