Flow-to-Flow Technology: Amide Formation in the Absence of Traditional Coupling Reagents Using DPDTC

The use of a recyclable coupling agent, 2,2’-dipyridyldithiocarbonate (DPDTC), has been demonstrated for the generation of isolable thioesters in a plug flow reactor (PFR). When isolation is not performed, the thioesters are directly reintroduced into the PFR, where coupling with amines is carried out to afford amides in a “flow-to-flow” process. Efficient coupling is achieved with both electron-rich and electron-poor aromatic acids, as well as sterically hindered aliphatic acids. A broad range of amines is successfully employed, allowing for the synthesis of Weinreb amides and peptides in high yields. The overall process is conducted under mild conditions, and high efficiency is maintained throughout.

• Saunders, JM
• Nava, EO
• Li, J
• Wong, MJ
• Freiberg, KM
• Lipshutz, BH

• Department of Chemistry & Biochemistry, University of California, Santa Barbara, California 93106, United States

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