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
Xinyu Zhou, Kemeng Zhang, Shuodan Ding, Lijin Wang, Mengtian Li, Ke Wang, Jie Zhou, Ge Wu
Abstract
We developed an unprecedented cascade reaction involving isocyanides with carboxylic acids and CD 3 SSO 3 Na to access S -CD 3 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 N -alkyl- N -formyl amide followed by thiolation with CD 3 SSO 3 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.