New Approach to Oximes through Reduction of Nitro Compounds Enabled by Visible Light Photoredox Catalysis

New Approach to Oximes through Reduction of Nitro Compounds Enabled by Visible Light Photoredox Catalysis

A range of nitro compounds are smoothly reduced to their corresponding oximes under the synergistic effects of visible light irradiation, the Ru(bpy)3Cl2 photocatalyst, Hünig’s base, Mg(ClO4)2 activation, and MeCN solvent. This remarkably mild and environmentally benign protocol, when orchestrated...

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Veröffentlicht in:Organic letters 2013-06, Vol.15 (11), p.2660-2663
Hauptverfasser: Cai, Shunyou, Zhang, Shaolong, Zhao, Yaohong, Wang, David Zhigang
Format: Artikel
Sprache:eng
Schlagworte:
Catalysis
Coordination Complexes - chemistry
Light
Magnesium Compounds - chemistry
Molecular Structure
Nitro Compounds - chemistry
Oxidation-Reduction
Oximes - chemical synthesis
Oximes - chemistry
Perchlorates - chemistry
Photochemical Processes
Ruthenium - chemistry
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Zusammenfassung:A range of nitro compounds are smoothly reduced to their corresponding oximes under the synergistic effects of visible light irradiation, the Ru(bpy)3Cl2 photocatalyst, Hünig’s base, Mg(ClO4)2 activation, and MeCN solvent. This remarkably mild and environmentally benign protocol, when orchestrated with classical Beckmann rearrangement, enables such high-value industrial feedstock as caprolactam to be readily accessed from simple precursor nitrocyclohexane.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol4009443