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使用磁性铜金属有机框架、二甲基亚砜作为溶剂和甲基源,通过C(sp2)-H活化实现咪唑并吡啶的C3-甲基化。

C3-methylation of imidazopyridines via C(sp2)-H activation using magnetic Cu-MOF, and DMSO as solvent and Methyl source.

作者信息

Moghaddam Firouz Matloubi, Pazoki Parisa Yaqubnezhad, Jarahiyan Atefeh, Aghamiri Bagher

机构信息

Laboratory of Organic Synthesis and Natural Products, Department of Chemistry, Sharif University of Technology, Azadi Street, 111559516, Tehran, Iran.

出版信息

Sci Rep. 2025 Aug 13;15(1):29727. doi: 10.1038/s41598-025-14556-1.

Abstract

In this study, we introduce a protocol for the methylation of the C-H bond at the C position in imidazo[1,2-a]pyridine scaffolds, employing magnetic def./Cu-MOF for the activation of C(sp2)-H bonds. The term 'def' refers to strategically induced defects in the Metal-Organic Framework (MOF), which are designed to improve its catalytic efficiency. These defects are generated using specific agents, with benzoic acid serving as the defect-promoting agent, leading to controlled structural imperfections within the MOF. This approach offers an efficient and reliable method for the methylation of imidazopyridines, showcasing excellent compatibility with various functional groups, high site selectivity, and outstanding product yields. Additionally, dimethyl sulfoxide acts as both the solvent and the source of methyl groups in the reaction, further streamlining the process.

摘要

在本研究中,我们介绍了一种在咪唑并[1,2 - a]吡啶骨架的C位进行C - H键甲基化的方案,采用磁缺陷/铜 - 金属有机框架(Cu - MOF)来活化C(sp2)-H键。术语“def”指的是在金属有机框架(MOF)中策略性引入的缺陷,其设计目的是提高其催化效率。这些缺陷是使用特定试剂产生的,苯甲酸作为缺陷促进剂,导致MOF内部产生可控的结构缺陷。这种方法为咪唑吡啶的甲基化提供了一种高效且可靠的方法,展示了与各种官能团的优异兼容性、高位点选择性和出色的产物收率。此外,二甲基亚砜在反应中既作为溶剂又作为甲基源,进一步简化了该过程。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1460/12350736/5bd046845bd1/41598_2025_14556_Fig1_HTML.jpg

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