Single point activation of pyridines enables reductive hydroxymethylation,Chemical Science

当前位置： X-MOL 学术 › Chem. Sci. › 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.)

Single point activation of pyridines enables reductive hydroxymethylation
Chemical Science ( IF 7.6 ) Pub Date : 2020-11-16 , DOI: 10.1039/d0sc05656a
Bruno Marinic ₁ , Hamish B Hepburn ₁ , Alexandru Grozavu ₁ , Mark Dow ₂ , Timothy J Donohoe ₁

Affiliation

The single point activation of pyridines, using an electron-deficient benzyl group, facilitates the ruthenium-catalysed dearomative functionalisation of a range of electronically diverse pyridine derivatives. This transformation delivers hydroxymethylated piperidines in good yields, allowing rapid access to medicinally relevant small heterocycles. A noteworthy feature of this work is that paraformaldehyde acts as both a hydride donor and an electrophile in the reaction, enabling the use of cheap and readily available feedstock chemicals. Removal of the activating group can be achieved readily, furnishing the free NH compound in only 2 steps. The synthetic utility of the method was illustrated with a synthesis of (±)-Paroxetine.

中文翻译：

吡啶的单点活化能够实现还原性羟甲基化

吡啶的单点活化，使用缺电子的苄基，促进了一系列电子多样化吡啶衍生物的钌催化的脱芳烃官能化。这种转化以良好的产率提供了羟甲基化哌啶，从而可以快速获得药用相关的小杂环。这项工作的一个值得注意的特点是多聚甲醛在反应中既充当氢化物供体又充当亲电子试剂，从而能够使用廉价且易于获得的原料化学品。去除活化基团很容易，只需 2 步即可提供游离 NH 化合物。该方法的合成效用通过 (±)-帕罗西汀的合成来说明。

更新日期：2020-11-16

点击分享查看原文

点击收藏

公开下载

阅读更多本刊最新论文本刊介绍/投稿指南11