ALIPHATIC THIOETHERS BY S-ALKYLATION OF THIOLS VIA TRIALKYL BORATES

作者:Gunes Deniz; Sirkecioglu Okan; Bicak Niyazi*
来源:Phosphorus, Sulfur, and Silicon and the Related Elements, 2010, 185(8): 1685-1690.
DOI:10.1080/10426500903213563

摘要

A simple and convenient one-pot procedure is described for the synthesis of thioethers via boron esters. This procedure involves in-situ generation of alkyl sulfates by reaction of trialkyl borates with concentrated sulfuric acid and subsequent reaction with thiols in the presence of pyridine. The reactions with boron esters of primary or secondary alcohols proceed cleanly at 100 degrees C and afford aliphatic thioethers in reasonable yields (59-93%) within 24 h. Interestingly, the 1H NMR spectra of the products showed no sign of positional isomerisms. The method fails however with thiophenol and does not yield aromatic thioethers, due to electrophilic substitution at the phenyl ring.

  • 出版日期2010

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