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Updated: Dec 15, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Dealkenylative Alkenylation: Formal σ-Bond Metathesis of Olefins
Manisha Swain1, Gusein Sadykhov1, Ruoxi Wang1
1Department of Chemistry and Biochemistry, University of California-Los Angeles, Los Angeles, CA, 90095-1569, USA.
Abstract:
The dealkenylative alkenylation of alkene C(sp3 )-C(sp2 ) bonds has been an unexplored area for C-C bond formation. Herein 64 examples of β-alkylated styrene derivatives, synthesized through the reactions of readily accessible feedstock olefins with β-nitrostyrenes by ozone/FeII -mediated radical substitutions, are reported. These reactions proceed with good efficiencies and high stereoselectivities under mild reaction conditions and tolerate an array of functional groups. Also demonstrated is the applicability of the strategy through several synthetic transformations of the products, as well as the syntheses of the natural product iso-moracin and the drug (E)-metanicotine.
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