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Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
Published on: September 8, 2013
Cascade Reaction of Isocyanides with Carboxylic Acid and CD3SSO3Na: Toward S-CD3 Thiocarbamates
Xinyu Zhou1, Kemeng Zhang1, Shuodan Ding1
1School of Pharmaceutical Sciences, Wenzhou Medical University, Wenzhou 325035, China.
Abstract:
We developed an unprecedented cascade reaction involving isocyanides with carboxylic acids and CD3SSO3Na to access S-CD3 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 CD3SSO3Na 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.
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