Chemoselective reduction of aromatic nitro compounds (o-nitrophenol derivatives) using simple borane-THF without transition metal catalysts, additives, or ligands

[Display omitted] Chemoselective reduction of aromatic nitro compounds (ortho-nitrophenol derivatives) using Borane in THF (BH3-THF) at room temperature, without using an additional metal catalyst is reported. Interestingly, nitroarenes containing two or three groups, a selective reduction of the ni...

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Bibliographic Details
Published in:Tetrahedron letters 2024-01, Vol.135, p.154899, Article 154899
Main Authors: Rode, Suryakant R., Mahajan, Prashant, Dadhaniya, Bhavik, Shirsath, Mahesh K., Thakur, Ravi, Doss, Rajesh, Khan, Nadeem A.
Format: Article
Language:English
Subjects:
Borane reduction
Chemoselective nitro group reduction
Intramolecular borane activation
Mild reduction of nitro groups
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Summary:[Display omitted] Chemoselective reduction of aromatic nitro compounds (ortho-nitrophenol derivatives) using Borane in THF (BH3-THF) at room temperature, without using an additional metal catalyst is reported. Interestingly, nitroarenes containing two or three groups, a selective reduction of the nitro group adjacent to the hydroxy group is observed which happens to be the first Chemoselective reduction protocol for nitro groups using BH3-THF. The presence of the phenolic hydroxyl group is found to be the key that aids in hydrogen transfer to the nitro group through a cyclic transition step.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2023.154899