Highly selective transition-metal-free transamidation of amides and amidation of esters at room temperature.,Nature Communications

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Highly selective transition-metal-free transamidation of amides and amidation of esters at room temperature.
Nature Communications ( IF 14.7 ) Pub Date : 2018-10-09 , DOI: 10.1038/s41467-018-06623-1
Guangchen Li ₁ , Michal Szostak ₁

Affiliation

Amide chemistry has an essential role in the synthesis of high value molecules, such as pharmaceuticals, natural products, and fine chemicals. Over the past years, several examples of transamidation reactions have been reported. In general, transition-metal-based catalysts or harsh conditions are employed for these transformations due to unfavorable kinetics and thermodynamics of the process. Herein, we report a significant advance in this area and present the general method for transition-metal-free transamidation of amides and amidation of esters by highly selective acyl cleavage with non-nucleophilic amines at room temperature. In contrast to metal-catalyzed protocols, the method is operationally-simple, environmentally-friendly, and operates under exceedingly mild conditions. The practical value is highlighted by the synthesis of valuable amides in high yields. Considering the key role of amides in various branches of chemical science, we envision that this broadly applicable method will be of great interest in organic synthesis, drug discovery, and biochemistry.

中文翻译：

在室温下进行高选择性的无过渡金属酰胺转酰胺化和酯酰胺化。

酰胺化学在药物、天然产物和精细化学品等高价值分子的合成中发挥着重要作用。在过去的几年中，已经报道了一些转酰胺基反应的例子。一般来说，由于过程的动力学和热力学不利，这些转化采用过渡金属基催化剂或苛刻的条件。在此，我们报告了该领域的重大进展，并提出了在室温下通过非亲核胺的高选择性酰基裂解进行酰胺的无过渡金属转酰胺化和酯酰胺化的一般方法。与金属催化方案相比，该方法操作简单、环境友好，并且在极其温和的条件下进行。高产率合成有价值的酰胺凸显了实用价值。考虑到酰胺在化学科学各个分支中的关键作用，我们预计这种广泛适用的方法将在有机合成、药物发现和生物化学领域引起极大的兴趣。

更新日期：2018-10-09

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