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Updated: May 17, 2025

Continuous Flow Chemistry: Reaction of Diphenyldiazomethane with p-Nitrobenzoic Acid
Published on: November 15, 2017
Flow-to-Flow Technology: Amide Formation in the Absence of Traditional Coupling Reagents Using DPDTC
John M Saunders1, Esveidy Oceguera Nava1, Jason Li1
1Department of Chemistry & Biochemistry, University of California, Santa Barbara, California 93106, United States.
Abstract:
Reported herein is the use of a recyclable coupling agent, 2,2'-dipyridyldithiocarbonate (DPDTC), that generates isolable thioesters in a plug flow reactor (PFR). If not isolated, thioesters can be reintroduced directly into the PFR, along with amines, to generate amides in a "flow-to-flow" sense. Both electron-rich and -poor aromatic acids, as well as sterically hindered aliphatic acids, are efficiently coupled with a variety of amines, including the formation of Weinreb amides and peptides, in high yields.
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