Palladium-Catalyzed One-Pot Synthesis of N-Formylaniline Derivatives Using Oxalic Acid as a Dual Carbon Monoxide and Hydrogen Donor

Org Lett. 2024 Oct 21. doi: 10.1021/acs.orglett.4c03714. Online ahead of print.

Abstract

A palladium-catalyzed three-component reaction enabled the synthesis of N-formylanilines from aryl iodides, NaN3, and oxalic acid. This one-pot process involves aminocarbonylation, the Curtius rearrangement, and reduction using oxalic acid as both a carbon monoxide and hydrogen donor. The method has a broad substrate scope, tolerates various functional groups, and delivers N-formylanilines in high yields, making it a green and useful synthetic approach.