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Updated: Sep 19, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Cu-Catalyzed Electrochemical Atom Transfer Radical Addition with Halomalonic Esters: A Route to Cyclopropane
Chuyi Su1, Masnun Naher1, Craig M Williams1
1School of Chemistry and Molecular Biosciences, University of Queensland, Brisbane 4072, Australia.
Abstract:
Atom transfer radical addition (ATRA) remains an important and popular synthetic method for C-C bond formation by using readily accessible alkene precursors and organic halides. We report that copper-catalyzed electrochemical ATRA (eATRA) of diethyl halomalonates (XCH(COOEt)2, X = Br, Cl) to a series of aromatic alkenes yields halide malonate ester intermediates that subsequently undergo facile ring closure to give cyclopropanes. The in situ spectroscopic identification of a diethyl malonatocopper(II) complex, [CuIIL(CH(COOEt)2)]+, serves as a key catalytic species, effectively moderating free radical concentrations during the electrochemical process to enhance product formation. Mechanistic insights into cyclopropanation were elucidated through cyclic voltammetry and UV-vis spectroelectrochemical analysis. This study presents a new mild electrochemical synthetic strategy for constructing functionalized cyclopropane derivatives.
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