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Updated: Oct 29, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Friedel-Crafts-Type Reactions with Electrochemically Generated Electrophiles from Donor-Acceptor Cyclopropanes and
Simon Kolb1, Nils L Ahlburg1, Daniel B Werz1
1Technische Universität Braunschweig, Institute of Organic Chemistry, Hagenring 30, 38106 Braunschweig, Germany.
Abstract:
We describe a general electrochemical method to functionalize donor-acceptor (D-A) cyclopropanes and -butanes with arenes utilizing Friedel-Crafts-type reactivity. The catalyst-free strategy relies on the direct anodic oxidation of the strained carbocycles, which leads after C(sp3)-C(sp3) cleavage to radical cations that act as electrophiles for the arylation reaction. Broad reaction scopes in regard to cyclopropanes, cyclobutanes, and aromatic reaction partners are presented. Additionally, a plausible electrolysis mechanism is proposed.
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