Photoinduced Reduction of Nitrobenzenes to Primary Aromatic Amines

Primary aromatic amines were synthesized from the corresponding nitrobenzenes via photoinduced reduction. The reaction was found to be effective when nitrobenzenes with electron-withdrawing substituents were irradiated with a broad band of UV light centered at 306 nm. When reactions are completed, p...

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Bibliographic Details
Published inSynlett Vol. 28; no. 10; pp. 1191 - 1194
Main Authors Huang, Hua-Hsuan, Chen, Yu-Feng, Niu, Guang-Hao, Chuang, Gary J.
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 19.06.2017
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
NITROARENES
nitrobenzenes
ACID
NITRO-COMPOUNDS
PHOTOREDUCTION
SELECTIVE REDUCTION
reduction
anilines
UV light
photoreaction
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Summary:Primary aromatic amines were synthesized from the corresponding nitrobenzenes via photoinduced reduction. The reaction was found to be effective when nitrobenzenes with electron-withdrawing substituents were irradiated with a broad band of UV light centered at 306 nm. When reactions are completed, products could be isolated by acid-base extraction or by column chromatography. This presenting photoreaction procedure for the synthesis of primary aromatic amines from the corresponding nitrobenzenes proceeds without the need of a sensitizer in isopropanol or THF. Without the usage of catalysts, or stoichiometric reducing reagent containing heavy metals, this photoinduced reduction of nitrobenzenes fulfils the concept of green chemistry.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0036-1588953