Flow-to-Flow Technology: Amide Formation in the Absence of Traditional Coupling Reagents Using DPDTC
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.
Authors
- Kaitlyn M. Freiberg (ORCID: https://orcid.org/0009-0007-1458-3859)
- Madison J. Wong (ORCID: https://orcid.org/0000-0001-8094-9678)
- Bruce H. Lipshutz (ORCID: https://orcid.org/0000-0001-9116-7049)
- Jason Li (ORCID: https://orcid.org/0000-0002-1150-3549)
- John M. Saunders
- Esveidy Oceguera Nava (ORCID: https://orcid.org/0000-0002-7215-7969)
Institutions
- University of California System (US)
Publication Details
- Journal
- ACS Sustainable Chemistry & Engineering
- Published
- 2025-04-29
- DOI
- https://doi.org/10.1021/acssuschemeng.5c00914
- Citations
- 2
- Primary Topic
- Innovative Microfluidic and Catalytic Techniques Innovation
- Type
- article
- Field-Weighted Citation Impact
- 1.35
Funders
- Division of Chemistry
- Division of Equity for Excellence in STEM