Cu-catalysed transamidation of unactivated aliphatic amides.

Vishal Kumar, Sanjeev Dhawan, Renu Bala, Sachin Balaso Mohite, Parvesh Singh, Rajshekhar Karpoormath

Organic & biomolecular chemistry 2022 Aug 31

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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.

Citation

Vishal Kumar, Sanjeev Dhawan, Renu Bala, Sachin Balaso Mohite, Parvesh Singh, Rajshekhar Karpoormath. Cu-catalysed transamidation of unactivated aliphatic amides. Organic & biomolecular chemistry. 2022 Aug 31;20(34):6931-6940