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

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 re...

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Bibliographic Details
Published in:New journal of chemistry 2024-05, Vol.48 (21), p.9424-9428
Main Authors: Cruz-Jiménez, Alicia Elvira, Argumedo-Castrejón, Paola Alejandra, Mateus-Ruiz, Jeferson B., Lucas-Rosales, Victor A., Valle-González, Octavio Adrián, Jiménez-Halla, J. Oscar C., Luján-Montelongo, J. Armando
Format: Article
Language:English
Subjects:
Amines
Catalysts
Deoxygenation
Formic acid
Oxides
Reducing agents
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Summary: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 Mg 2+ /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.
ISSN:1144-0546
1369-9261
DOI:10.1039/D4NJ00913D