Electrochemically Enabled Direct C3-Formylation of Imidazopyridines with Me3 N as a Carbonyl Source

Chem Asian J. 2023 Apr 3;18(7):e202300001. doi: 10.1002/asia.202300001. Epub 2023 Mar 1.

Abstract

A metal-free and oxidant-free electrochemically enabled strategy for C-3 formylation of imidazopyridines using trimethylamine as a one-carbon source has been established. This conversion has high functional group compatibility under mild conditions and ensures late-stage functionalization of pharmaceutical molecules. Furthermore, unexpected hexafluoroisopropoxylation products have been observed in some cases. Mechanistic studies using cyclic voltammetry and control experiments reveal the key intermediate of the formylation process.

Keywords: electrochemical oxidation; formylation; green chemistry; imidazopyridines; trimethylamine.