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Iodine-mediated aminohalogenation-oxidation to synthesize 2-fluoroalkyl imidazole derivatives

Shan Li, Jian Liang, Xiaofeng Liu, Liqing Xian, and Mingxu Du

Laboratory of Regional Ecological Environment Analysis and Pollution Control of West Guangxi, College of Chemistry and Environment Engineering, Baise University, Baise, China

 

E-mail: lishan0914@163.com

Received: 25 July 2020  Accepted: 14 September 2020

Abstract:

A simple and efficient method of iodine-mediated aminohalogenation-oxidation of fluorinated N’-propargyl amidines to synthesize 2-fluoroalkyl imidazole-5-carbaldehydes was developed. This method showed good functional group compatibility and wide substrate scope, as variety of substituted substrates proceeded smoothly to give the corresponding products in moderate to excellent yields. And this method was also suitable to unfluorinated substrates. Fluorinated allyl amidines used as starting materials, aminohalogenated products were obtained as the final products. Studies on the mechanism indicated that the carbonylation proceeded via 5-iodomethyl imidazole intermediate, and the carbonyl oxygen atom was demonstrated that originated from dioxygen.

Keywords: Iodine-mediated; Propargyl amidine; Aminohalogenation-oxidation; Imidazole-5-carbaldehyde; 5-iodomethyl imidazole

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-020-01360-6

 

Chemical Papers 75 (3) 1041–1053 (2021)

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