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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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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Abstract 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.
AbstractList 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.
Author Niu, Guang-Hao
Chen, Yu-Feng
Huang, Hua-Hsuan
Chuang, Gary J.
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  givenname: Yu-Feng
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  givenname: Gary J.
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  fullname: Chuang, Gary J.
  email: gjchuang@cycu.edu.tw
  organization: Chung Yuan Christian Univ, Dept Chem, 200 Chung Pei Rd, Taoyuan 32023, Taiwan
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CitedBy_id crossref_primary_10_1021_acs_joc_7b01887
crossref_primary_10_1007_s41981_021_00190_1
crossref_primary_10_1002_cptc_202300236
Cites_doi 10.1016/j.tetlet.2013.11.023
10.1016/j.tetlet.2007.12.075
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10.1002/chem.201504685
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Issue 10
Keywords NITROARENES
nitrobenzenes
ACID
NITRO-COMPOUNDS
PHOTOREDUCTION
SELECTIVE REDUCTION
reduction
anilines
UV light
photoreaction
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Snippet Primary aromatic amines were synthesized from the corresponding nitrobenzenes via photoinduced reduction. The reaction was found to be effective when...
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Chemistry, Organic
Physical Sciences
Science & Technology
Title Photoinduced Reduction of Nitrobenzenes to Primary Aromatic Amines
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