Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 20, Issue 34, Pages 6931-6940Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d2ob01152b
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Funding
- National Research Foundation-South Africa (NRF-SA) [129247, 145946]
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Direct transamidation is a groundbreaking technique that generates various amides without the need for acid-amine coupling or other intermediate steps. In this study, we successfully achieved transamidation of unactivated aliphatic amides using a copper catalyst and chlorotrimethylsilane as an additive. Furthermore, we utilized transamidation as a tool for selective N-C(O) cleavage and O-C(O) formation to synthesize 2-substituted benzoxazoles and benzothiazoles.
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.
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