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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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Published in: | Organic letters 2021-07, Vol.23 (14), p.5549-5553 |
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Main Authors: | , , |
Format: | Article |
Language: | English |
Citations: | Items that this one cites Items that cite this one |
Online Access: | Get full text |
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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. |
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ISSN: | 1523-7060 1523-7052 |
DOI: | 10.1021/acs.orglett.1c01890 |