Citation: Xiao-Chun Yu, Bo Li, Bao-Hua Yu, Qing Xu. Efficient synthesis of unsymmetrical diaryl thioethers via TBAF-mediated denitrative substitution of nitroarenes with PhSTMS under mild and neutral conditions[J]. Chinese Chemical Letters, ;2013, 24(07): 605-608. shu

Efficient synthesis of unsymmetrical diaryl thioethers via TBAF-mediated denitrative substitution of nitroarenes with PhSTMS under mild and neutral conditions

1.
College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325035, China

Corresponding author: Qing Xu,
Received Date: 23 January 2013
Available Online: 8 April 2013

Tetrabutylammonium fluoride (TBAF) effectively facilitated a denitrative substitution reaction of electron-deficient nitroarenes with phenylthiotrimethylsilane (PhSTMS) under mild and base-free neutral conditions at room temperature, providing a practical and efficient synthesis of useful unsymmetrical diaryl thioethers. Nitroarenes bearing ortho-and para-positioned electron-withdrawing groups are the most reactive substrates, indicating that this reaction most possibly proceeded via the nucleophilic aromatic substitution (S_NAr) mechanism.
- Phenylthiotrimethylsilane,
- Nitroarenes,
- Denitrative substitution,
- Unsymmetrical diaryl thioethers,
- Nucleophilic aromatic substitution
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沈阳化工大学材料科学与工程学院沈阳 110142