Iodine-mediated aminohalogenation-oxidation to synthesize 2-fluoroalkyl imidazole derivatives
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ORIGINAL PAPER
Iodine‑mediated aminohalogenation‑oxidation to synthesize 2‑fluoroalkyl imidazole derivatives Shan Li1 · Jian Liang1 · Xiaofeng Liu1 · Liqing Xian2 · Mingxu Du1 Received: 25 July 2020 / Accepted: 14 September 2020 © Institute of Chemistry, Slovak Academy of Sciences 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
Introduction Fluorine was featured by unique chemical properties for the smaller atomic radius and the strongest electronegativity. The selective introduction of a fluorine atom or fluorinecontaining group into organic molecules would dramatically modulate their lipophilicity, metabolic stability, bioavailability, and other properties (Groult et al. 2017; Kirsch 2012; Gouverneur et al. 2012). Be provided with new characteristics, fluorinated compounds are omnipresent in pharmaceuticals, agrochemicals, energetic materials, and other highvalue chemical products (wang et al. 2014; Meanwell 2011; Purser et al. 2008). Despite great progress in constructing C-F and C-Rf over the past decade (Sather et al. 2016; Yang Electronic supplementary material The online version of this article (https://doi.org/10.1007/s11696-020-01360-6) contains supplementary material, which is available to authorized users. * Shan Li [email protected] 1
Laboratory of Regional Ecological Environment Analysis and Pollution Control of West Guangxi, College of Chemistry and Environment Engineering, Baise University, 21 Zhongshan No.2 Road, Baise 533000, China
School of Materials Science and Engineering, Baise University, 21 Zhangshan No. 2 Road, Baise 533000, China
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et al. 2015; Concepción et al. 2015; Liu et al. 2015), exploring a simple and efficient strategy to synthesize compounds with a fluorine atom or fluoroalkyl group at a desirable position in a highly controllable manner is still demanding. Imidazoles which possess prominent chemical properties and physiological activity are common nitrogen heterocyclic compounds in bioactive molecules (Zhang et al. 2014; Jin et al. 2014). However, the numbers of pharmaceuticals, agrochemicals and other materials comprising fluorinated imidazoles remain limited for only few strategies that dedicate for constructing imidazole with
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