A Versatile Approach to Dynamic Amide Bond Formation with Imine Nucleophiles. Issue 25 (21st April 2020)

• Record Type: Journal Article
• Authors: Erguven, Huseyin; Keyzer, Evan N.; Arndtsen, Bruce A.
• Is Part Of: Chemistry. Volume 26:Issue 25(2020)
• Page Start: 5709
• Page End: 5716
• Publication Date: 2020-04-21
• Subjects: amide synthesis -- dynamic covalent chemistry -- iminium salts -- macrocycles -- organic synthesis; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.202001140
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: 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. Abstract : Amide synthesis : An approach to the dynamic formation of amides is described. This method uses the reversible reaction between imines and acyl chlorides, occurs at ambient conditions, and does not require catalysts. Moreover, coupling this reaction with hydrolysis can be used to achieve the overall formation of robust products, and can be applied to the controlled assembly of various amide‐based materials (see scheme).