Issue 34, 2022

Cu-catalysed transamidation of unactivated aliphatic amides

Abstract

Direct transamidation is gaining prominence as a ground-breaking technique that generates a wide variety of amides without the requirement of acid–amine coupling or other intermediate steps. However, transamidation of unactivated aliphatic amides, on the other hand, has been a long-standing issue in comparison to transamidation of activated amides. Herein, we report a transamidation approach of an unactivated aliphatic amide using a copper catalyst and chlorotrimethylsilane as an additive. In addition, we used transamidation as a tool for selective N–C(O) cleavage and O–C(O) formation to synthesise 2-substituted benzoxazoles and benzothiazoles. The reactions were carried out without using any solvents and offered wide substitution scope.

Graphical abstract: Cu-catalysed transamidation of unactivated aliphatic amides

Supplementary files

Article information

Article type
Paper
Submitted
26 Jun 2022
Accepted
02 Aug 2022
First published
19 Aug 2022

Org. Biomol. Chem., 2022,20, 6931-6940

Cu-catalysed transamidation of unactivated aliphatic amides

V. Kumar, S. Dhawan, R. Bala, S. B. Mohite, P. Singh and R. Karpoormath, Org. Biomol. Chem., 2022, 20, 6931 DOI: 10.1039/D2OB01152B

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