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可见光诱导的咪唑并[1,2-]吡啶与α-氨基酸衍生物和α-氨基酮的脱氢亚胺化反应。

Visible-Light-Induced Dehydrogenative Imidoylation of Imidazo[1,2-]pyridines with α-Amino Acid Derivatives and α-Amino Ketones.

机构信息

Jiangxi Province Key Laboratory of Synthetic Chemistry, School of Chemistry, Biology and Materials Science, East China University of Technology, Nanchang 330013, China.

Ministry of Education Key Laboratory of Functional Small Organic Molecule, Department of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang 330022, China.

出版信息

J Org Chem. 2020 Dec 4;85(23):15062-15071. doi: 10.1021/acs.joc.0c01940. Epub 2020 Nov 2.

Abstract

A new and efficient visible-light-promoted dehydrogenative cross-coupling reaction of imidazo[1,2-]pyridines with α-amino carbonyl compounds toward imidoyl imidazo[1,2-]pyridines is developed. A diverse range of imidazo[1,2-]pyridines undergoes the dehydrogenative imidoylation smoothly with α-amino carbonyl compounds to access the corresponding products in satisfactory yields. We have also proposed the possible reaction mechanism based on preliminary mechanistic studies. The synthetic method has the advantages of wide substrate scope, good functional tolerance, and mild reaction conditions, which make this transformation more practical and sustainable.

摘要

发展了一种新的、高效的可见光促进的咪唑并[1,2-a]吡啶与α-氨基羰基化合物的脱氢交叉偶联反应,用于合成酰基咪唑并[1,2-a]吡啶。各种咪唑并[1,2-a]吡啶与α-氨基羰基化合物顺利地进行脱氢酰化反应,以令人满意的收率得到相应的产物。我们还根据初步的机理研究提出了可能的反应机理。该合成方法具有广泛的底物范围、良好的官能团容忍度和温和的反应条件等优点,使这种转化更具实际意义和可持续性。

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