Visible Light-Induced Divergent Deoxygenation/Hydroxymethylation of Pyridine N-Oxides

J Org Chem. 2025 Jan 24;90(3):1376-1387. doi: 10.1021/acs.joc.4c02770. Epub 2025 Jan 9.

Abstract

This study explores the deoxygenation of pyridine N-oxides and presents a one-step photoredox method for the direct synthesis of 2-hydroxymethylated pyridines from pyridine N-oxides. Mechanism studies elucidate the role of the catalyst and provide evidence of the possible electron transfer process and the formation of key radicals. A range of pyridine derivatives, particularly 2-hydroxymethyl-substituted pyridines, which may be difficult to obtain, can be synthesized in a single step.