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Friedel–Crafts-Type Reactions with Electrochemically Generated Electrophiles from Donor–Acceptor Cyclopropanes and -Butanes

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...

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Bibliographic Details
Published in:Organic letters 2021-07, Vol.23 (14), p.5549-5553
Main Authors: Kolb, Simon, Ahlburg, Nils L, Werz, Daniel B
Format: Article
Language:English
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c01890