Two-step continuous-flow synthesis of 6-membered cyclic iodonium salts via anodic oxidation

Abstract

We describe a multi-step continuous-flow procedure for the generation of six-membered diaryliodonium salts. The accompanying scalability and atom economy are significant improvements to existing batch methods. Benzyl acetates are submitted to this two-step procedure as highly available and cheap starting materials. An acid-catalyzed Friedel–Crafts alkylation followed by an anodic oxidative cyclization yielded a defined set of cyclic iodonium salts in a highly substrate-dependent yield.

Keywords

• electrochemistry
• flow chemistry
• hypervalent compounds
• iodine
• oxidation