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Article Dans Une Revue Journal of Organic Chemistry Année : 2021

Iron-Catalyzed Hydrogen Transfer Reduction of Nitroarenes with Alcohols: Synthesis of Imines and Aza Heterocycles

Résumé

A straightforward and selective reduction of nitroarenes with various alcohols was efficiently developed using an iron catalyst via a hydrogen transfer methodology. This protocol led specifically to imines in 30-91% yields, with a good functional group tolerance. Noticeably, starting from o-nitroaniline derivatives, in the presence of alcohols, benzimidazoles can be obtained in 64-72% yields when the reaction was performed with an additional oxidant, DDQ, and quinoxalines were prepared from 1,2-diols in 28-96% yields. This methodology, unprecedented at iron for imines, also provides a sustainable alternative for the preparation of quinoxalines and benzimidazoles.

Domaines

Chimie
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Dates et versions

hal-03102122 , version 1 (07-01-2021)

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Citer

Jiajun Wu, Christophe Darcel. Iron-Catalyzed Hydrogen Transfer Reduction of Nitroarenes with Alcohols: Synthesis of Imines and Aza Heterocycles. Journal of Organic Chemistry, 2021, 86 (1), pp.1023-1036. ⟨10.1021/acs.joc.0c02505⟩. ⟨hal-03102122⟩
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