Development of a Triazinyluronium-Based Dehydrative Condensing Reagent with No Heteroatomic Bonds
A triazinyluronium-based dehydrative condensing reagent, 2-(4,6-dimethoxy-1,3,5-triazin-2-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (DMT-TU), has been developed. Unlike commonly used guanidinium- and uronium-based reagents, DMT-TU does not contain high-energy N-N and N-O bonds, reducing its explosivity, as suggested by differential scanning calorimetry. Using DMT-TU in the presence of <sup><i>i</i></sup>Pr<sub>2</sub>EtN at room temperature, carboxylic acids and amines were effectively converted to their corresponding amides. Additionally, peptide bond formation with DMT-TU exhibited suppressed racemization ratios.
Authors
- Munetaka Kunishima (ORCID: https://orcid.org/0000-0002-3296-490X)
- Hikaru Fujita (ORCID: https://orcid.org/0000-0002-0430-9705)
- Gaku Mizushima
Institutions
- Kanazawa University (JP)
- Kobe Gakuin University (JP)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2024-12-03
- DOI
- https://doi.org/10.1021/acs.joc.4c02075
- Citations
- 4
- Primary Topic
- Chemical Synthesis and Analysis
- Type
- article
- Field-Weighted Citation Impact
- 0.94
Funders
- Ministry of Education, Culture, Sports, Science and Technology
- Japan Society for the Promotion of Science