Work

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

Year: 2025

Type: article

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.

Source: ACS Sustainable Chemistry & Engineering

DOI: 10.1021/acssuschemeng.5c00914

Authors: John M. Saunders, Esveidy Oceguera Nava, Jason Li, Madison J. Wong, Kaitlyn M. Freiberg, Bruce H. Lipshutz

Language: English

Topic: Chemical Synthesis and Analysis

Subfield: Molecular Biology

Field: Biochemistry, Genetics and Molecular Biology

Domain: Life Sciences

SDG: Responsible consumption and production

Open Access status: hybrid

Estimated APC paid: $4,500

Funders: National Science Foundation, Division of Chemistry, Division of Equity for Excellence in STEM