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钯催化 2,4-二氯吡啶 C-4 选择性偶联及合成用于活细胞成像的吡啶基染料。

Palladium-Catalyzed C-4 Selective Coupling of 2,4-Dichloropyridines and Synthesis of Pyridine-Based Dyes for Live-Cell Imaging.

机构信息

Department of Forensic Science, Oil-tea in Medical Health Care and Functional Product Development Engineering Research Center in Jiangxi, Gannan Medical University, 1 Yixueyuan Road, Ganzhou, Jiangxi 341000, China.

Department of Chemistry, Jiangxi University of Science and Technology, 86 Hongqi Road, Ganzhou 341000, China.

出版信息

J Org Chem. 2020 May 15;85(10):6498-6508. doi: 10.1021/acs.joc.0c00449. Epub 2020 May 4.

Abstract

An alternative process of Pd-catalyzed C-4 selective coupling of 2,4-dichloropyridines with boronic esters was developed, which afforded 24 examples of C-4 coupled pyridines in moderate to good yields. After further arylation, 21 examples of C-2, C-4 diarylated pyridines with a significant photophysical property were obtained, which were applied as pyridine-based dyes into live-cell imaging with good biocompatibility and low toxicity.

摘要

发展了一种钯催化的 2,4-二氯吡啶与硼酸酯 C-4 选择性偶联的替代方法,该方法以中等至良好的收率得到了 24 个 C-4 偶联吡啶的实例。进一步芳基化后,得到了 21 个具有显著光物理性质的 C-2、C-4 二芳基吡啶的实例,这些吡啶基染料具有良好的生物相容性和低毒性,可应用于活细胞成像。

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