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Updated: May 15, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Silver-Catalyzed Doyle-Kirmse Reaction of Allyl Sulfides with Vinyl Triftosylhydrazones
Ziying Li1, Zhaohong Liu1, Paramasivam Sivaguru1
1Department of Chemistry, Northeast Normal University, Changchun 130024, China.
Abstract:
Here, we report a general and practical Doyle-Kirmse reaction of allyl/propargyl sulfides with donor-only vinyl carbenes generated in situ from vinyl triftosylhydrazones in the presence of a silver catalyst. This protocol features mild conditions, exhibits a broad substrate scope and exceptional functional group tolerance, and provides corresponding 1,5-dienyl and 1,4-enallenyl sulfides in high yields. Moreover, gram-scale synthesis, late-stage modifications of complex molecules, and post-synthetic transformations were performed to demonstrate the applicability of this protocol.
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