Department of Chemistry, McGill University, 801 Sherbrooke St. W, Montreal, Quebec, H3A0B8, Canada.
Chemistry. 2020 May 4;26(25):5709-5716. doi: 10.1002/chem.202001140. Epub 2020 Apr 21.
Dynamic covalent chemistry has rapidly become an important approach to access supramolecular structures. While the products generated in these reactions are held together by covalent bonds, the reversible nature of the transformations can limit the utility of many these systems in creating robust materials. We describe herein a method to form stable and commonly employed amide bonds by exploiting the reversible coupling of imines and acyl chlorides. The reaction employs easily accessible reagents, is dynamic under ambient conditions, without catalysts, and can be trapped with simple hydrolysis. This offers an approach to create broad families of amide products under thermodynamic control, including the selective formation of amide macrocycles or polymers.
动态共价化学已迅速成为获取超分子结构的重要方法。虽然这些反应生成的产物是通过共价键结合在一起的，但转化的可逆性质可能会限制许多此类系统在制造坚固材料方面的应用。本文介绍了一种通过利用亚胺和酰氯的可逆偶联来形成稳定且常用的酰胺键的方法。该反应使用易于获得的试剂，在环境条件下是动态的，无需催化剂，并且可以通过简单的水解来捕获。这为在热力学控制下创建广泛的酰胺产物提供了一种方法，包括酰胺大环或聚合物的选择性形成。
