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

• DOI: 10.1021/acs.orglett.1c01890
• Publication Date: 2021-07-07T12:29:31Z
• Authors: Simon Kolb; Nils L. Ahlburg; Daniel B. Werz
• Keywords: Cyclobutanes; Friedel–Crafts reaction; Reactivity; Cleavage (geology); Acceptor

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 strained carbocycles, which leads after C(sp3)–C(sp3) cleavage radical cations that act as electrophiles for arylation reaction. Broad reaction scopes in regard cyclopropanes, cyclobutanes, aromatic partners are presented. Additionally, plausible electrolysis mechanism is proposed.