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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.
Tetrabutylammonium fluoride (TBAF) efficiently 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 asymmetrical diaryl thioethers. Nitroarenes bearing ortho-and para-positioned electron-withdrawing groups are the most reactive substrates, indicating that this reaction most probably proceeded via the nucleophilic aromatic substitution (S_NAr) mechanism.