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

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.