Copper-Catalyzed Chan-Lam Coupling of NH-Diaryl Sulfondiimines,Advanced Synthesis & Catalysis

当前位置： X-MOL 学术 › Adv. Synth. Catal. › 论文详情

Our official English website, www.x-mol.net, welcomes your feedback! (Note: you will need to create a separate account there.)

Copper-Catalyzed Chan-Lam Coupling of NH-Diaryl Sulfondiimines
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2022-05-10 , DOI: 10.1002/adsc.202200279
Yangyang Wang ₁ , Tingting Meng ₂ , Shuaisong Su ₂ , Limin Han ₁ , Ning Zhu ₁ , Tiezheng Jia ₂

Affiliation

Sulfondiimines, which contain a tetrasubstituted sulfur centre bearing two nitrogens and two carbon substituents, are a class of underexplored scaffolds in organic chemistry. Fascinated by some unique yet intriguing properties, sulfondiimines appear as leads in discovery industry, but the lack of efficient synthetic approaches holds back their further uptake by medicinal chemistry. Herein, a general and practical copper-catalyzed Chan-Lam coupling of NH-diaryl sulfondiimines with arylboronic acids is presented. A simple copper catalyst efficiently facilitated the highly chemoselective construction of C−N bond, allowing the preparation of a variety of N-arylated diaryl sulfondiimines in good yields under mild and environmentally benign conditions. An array of protecting groups on imine moieties were well tolerated, offering diversified accesses to NH,NAr-diaryl sulfondiimines, a class of versatile building blocks. Moreover, an aza-analogue of an EphB4 inhibitor featuring a sulfondiimine-based pharmacophore was generated employing our Chan-Lam coupling as the key step.

中文翻译：

NH-二芳基磺二亚胺的铜催化 Chan-Lam 偶联

磺二亚胺含有一个四取代的硫中心，带有两个氮和两个碳取代基，是有机化学中一类尚未开发的支架。磺二亚胺被一些独特而有趣的特性所吸引，在发现行业中出现了领先地位，但缺乏有效的合成方法阻碍了它们在药物化学中的进一步应用。本文介绍了一种通用且实用的铜催化N H-二芳基磺二亚胺与芳基硼酸的 Chan-Lam 偶联。一种简单的铜催化剂有效地促进了 C-N 键的高度化学选择性构建，从而可以制备多种N-芳基化二芳基磺二亚胺在温和和环境友好的条件下具有良好的收率。亚胺部分上的一系列保护基团具有良好的耐受性，为N H、N Ar-二芳基磺二亚胺（一类多功能的结构单元）提供了多种途径。此外，采用我们的 Chan-Lam 偶联作为关键步骤，生成了一种具有基于磺二亚胺的药效团的 EphB4 抑制剂的氮杂类似物。

更新日期：2022-05-10

点击分享查看原文

点击收藏

阅读更多本刊最新论文本刊介绍/投稿指南11