News & Events

Jarrod Stanley

Posted on April 21, 2021


Date - April 21, 2021
1:00 pm - 2:00 pm


Thesis Title: Palladium Catalyzed Dehydration of Primary Amides: Step Economical Synthesis of Vildagliptin

Advisor: Dr. Mitchell Croatt


The research presented involves the conversion of primary amides to nitriles using a Selectfluor-modified palladium(II) catalyst in acetonitrile. The dehydration conditions are mild and can be applied to a diverse substrate scope. The development of this efficient and highly chemoselective reaction further enables the installation of nitrile functional groups. The utility of this dehydration strategy is exemplified in a 3-step in situ synthesis of Vildagliptin, an anti-hyperglycemic agent. Readily available starting materials are acylated, undergo a substitution reaction, and consequently subjected to dehydration conditions to yield Vildagliptin. Palladium catalyzed dehydrations of primary amides to generate nitriles are diverse in application and have cornerstone potential for organic synthesis.