Issue 21, 2024

Deoxygenation of heterocyclic N-oxides employing iodide and formic acid as a sustainable reductant

Abstract

We present a novel deoxygenation method for heterocyclic N-oxides utilizing iodide as a catalyst. Iodide acts as a reducing catalyst that is regenerated by formic acid, which also serves as a Brønsted activator and solvent. The method demonstrates high efficiency and excellent selectivity in the reduction of a variety of heterocyclic N-oxides and tertiary amines. Our computational DFT investigation revealed that the reduction mechanism entails a direct interaction between iodide and the oxygen of the N-oxide within a Mg2+/formic acid framework, resulting in the formation of the N-heterocycle and the release of a hypoiodite unit. Additionally, a molecular mechanism for the regeneration of iodide from hypoiodite, facilitated by formic acid, is suggested. This method provides an environmentally friendly approach for the deoxygenation of N-oxides and related species.

Graphical abstract: Deoxygenation of heterocyclic N-oxides employing iodide and formic acid as a sustainable reductant

Supplementary files

Article information

Article type
Communication
Submitted
26 Feb 2024
Accepted
09 May 2024
First published
09 May 2024
This article is Open Access
Creative Commons BY-NC license

New J. Chem., 2024,48, 9424-9428

Deoxygenation of heterocyclic N-oxides employing iodide and formic acid as a sustainable reductant

A. E. Cruz-Jiménez, P. A. Argumedo-Castrejón, J. B. Mateus-Ruiz, V. A. Lucas-Rosales, O. A. Valle-González, J. O. C. Jiménez-Halla and J. A. Luján-Montelongo, New J. Chem., 2024, 48, 9424 DOI: 10.1039/D4NJ00913D

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