Cascade Reaction of Isocyanides with Carboxylic Acid and CD<sub>3</sub>SSO<sub>3</sub>Na: Toward <i>S</i>-CD<sub>3</sub> Thiocarbamates
We developed an unprecedented cascade reaction involving isocyanides with carboxylic acids and CD<sub>3</sub>SSO<sub>3</sub>Na to access <i>S</i>-CD<sub>3</sub> thiocarbamates with the formation of two C-N bonds and one C-S bond. Preliminary mechanistic investigations disclose that these three-component reactions precede the esterification of carboxylic acids with isocyanides, generating a capable <i>N</i>-alkyl-<i>N</i>-formyl amide followed by thiolation with CD<sub>3</sub>SSO<sub>3</sub>Na to provide the corresponding products. The transformation has outstanding features in mild reaction conditions, effortless experimental operation, structural modification of polyfunctional carboxylic acid drugs, and large-scale preparation.
Authors
- Xinyu Zhou (ORCID: https://orcid.org/0000-0003-1399-828X)
- Jie Zhou (ORCID: https://orcid.org/0000-0003-3389-7515)
- Ge Wu (ORCID: https://orcid.org/0000-0001-8432-5272)
- Mengtian Li
- Kemeng Zhang
- Shuodan Ding
- Ke Wang (ORCID: https://orcid.org/0000-0003-3812-7018)
- Lijin Wang (ORCID: https://orcid.org/0000-0003-4359-5289)
Institutions
- Chinese Academy of Sciences (CN)
- Wenzhou Medical University (CN)
- Fujian Institute of Research on the Structure of Matter (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-04-29
- DOI
- https://doi.org/10.1021/acs.orglett.5c01166
- Citations
- 29
- Primary Topic
- Sulfur-Based Synthesis Techniques
- Type
- article
- Field-Weighted Citation Impact
- 27.15
Funders
- National Natural Science Foundation of China
- State Key Laboratory of Structural Chemistry
- Natural Science Foundation of Zhejiang Province