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Updated: Mar 7, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
Sc(OTf)3-catalyzed synthesis of anhydrides from twisted amides
Yongmei Liu1, Ruzhang Liu2, Michal Szostak3
1College of Chemistry and Chemical Engineering, Yangzhou University, 180 Siwangting Road, Yangzhou 225002, China and Department of Chemistry, Rutgers University, 73 Warren Street, Newark, NJ 07102, USA. michal.szostak@rutgers.edu.
Abstract:
A novel synthesis of anhydrides from twisted amides is reported. Sc(OTf)3 catalysis in the presence of water is used to synthesize anhydrides in one step from amides without external nucleophiles. Mechanistic studies indicate that the coordination of the catalyst is critical to induce the challenging N-C activation step. This process further highlights the utility of twisted amides in organic synthesis. Notably, the reaction indicates that twisted amides based on the glutarimide scaffold are more reactive than carboxylic acid anhydrides under the developed conditions, which opens the door to controlled sequential catalysis through amide N-C bond cleavage.
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