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Updated: Jul 17, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Palladium(II)-Catalyzed Decarboxylative Difunctionalization of Alkynoic Acids To Access (E)-β-Sulfonylacrylamides and
Shashank Tripathi1,2, Monty Kumar1,2, Ayush Shivhare3
1Medicinal and Process Chemistry, CSIR-Central Drug Research Institute, Lucknow 226031, India.
Abstract:
A palladium(II)-catalyzed regio- and stereoselective difunctionalization of alkynoic acids has been achieved using sodium sulfinates and isocyanides to synthesize (E)-β-sulfonylacrylamides. The reaction proceeds via decarboxylative isocyanide addition, followed by sulfonylation. This three-component process works well with aromatic, heteroaromatic, and aliphatic alkynoic acids with good functional group tolerance and excellent regio- and stereoselectivity. DFT calculations were carried out to explain the reaction mechanism and the stereoselective formation of (E)-β-sulfonylacrylamides.
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