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Pre-electrolysis of LiClO(4) in Acetonitrile: Electrochemically Induced Protolytic Carbon–Carbon Bond Formation of Benzylic Ethers and Acetals with Allyl Trimethylsilane and Other Carbon Nucleophiles

[Image: see text] The pre-electrolysis of LiClO(4) in acetonitrile in an undivided cell applying only “catalytic” amounts of current (e.g., 0.05 F) led to the formation of a strong acidic medium for the activation of benzylic ethers and acetals. The activated primary and secondary benzylic ethers an...

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Detalles Bibliográficos
Autores principales: Fastie, Cornelius, Li, Luomo, Bätcher, Moritz, Hilt, Gerhard
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10476155/
https://www.ncbi.nlm.nih.gov/pubmed/37594465
http://dx.doi.org/10.1021/acs.joc.3c01256
Descripción
Sumario:[Image: see text] The pre-electrolysis of LiClO(4) in acetonitrile in an undivided cell applying only “catalytic” amounts of current (e.g., 0.05 F) led to the formation of a strong acidic medium for the activation of benzylic ethers and acetals. The activated primary and secondary benzylic ethers and acetals could be converted with a range of carbon nucleophiles, such as allyl trimethylsilane, silyl enol ethers, and enol acetates, for the formation of new carbon–carbon bonds. A chemoselective reaction was observed when electron-deficient benzylic acetals were converted with allyl trimethylsilane to the monoallylated products, whereas an electron-rich benzylic acetal led to the double allylated product under activation of both ether groups.