Friedel–Crafts Alkylation with Carbenium Ions Generated by Electrochemical Oxidation of Stannylmethyl Ethers

European Journal of Organic Chemistry 2020
Anna Lielpētere, Aigars Jirgensons

The electrochemical activation of stannylmethyl ethers was exploited for Friedel–Crafts alkylation of arenes at near-neutral conditions. Single cell anodic oxidation of stannylmethyl ethers leads to oxonium ions which fragment to carbenium ions in the presence of electron rich arenes. Low oxidation potential of stannylmethyl ethers and buffered conditions enable the Friedel–Crafts reaction with a wide range of arenes including the substrates with acid-sensitive groups.

Keywords
Anodic oxidation, Carbenium ion, Electrochemistry, Friedel–Crafts reaction, Stannylmethyl ethers
DOI
10.1002/ejoc.202000568
Hyperlink
https://chemistry-europe.onlinelibrary.wiley.com/doi/full/10.1002/ejoc.202000568

Lielpētere, A., Jirgensons, A. Friedel–Crafts Alkylation with Carbenium Ions Generated by Electrochemical Oxidation of Stannylmethyl Ethers. European Journal of Organic Chemistry, 2020, Vol. 2020, No. 29, pp.4510-4516. ISSN 1434-193X. e-ISSN 1099-0690. Available from: doi:10.1002/ejoc.202000568

Publication language
English (en)