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Updated: Sep 2, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Dealkenylative Alkynylation Using Catalytic FeII and Vitamin C
Manisha Swain1, Thomas B Bunnell1, Jacob Kim1
1Department of Chemistry and Biochemistry, University of California─Los Angeles, Los Angeles, California 90095-1569, United States.
Abstract:
In this paper, we report the synthesis of alkyl-tethered alkynes through ozone-mediated and FeII-catalyzed dealkenylative alkynylation of unactivated alkenes in the presence of alkynyl sulfones. This one-pot reaction, which employs a combination of a catalytic FeII salt and l-ascorbic acid, proceeds under mild conditions with good efficiency, high stereoselectivity, and broad functional group compatibility. In contrast to our previous FeII-mediated reductive fragmentation of α-methoxyhydroperoxides, the FeII-catalyzed process was devised through a thorough kinetic analysis of the multiple competing radical (redox) pathways. We highlight the potential of this dealkenylative alkynylation through multiple post-synthetic transformations and late-stage diversifications of complex molecules, including natural products and pharmaceuticals.
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