Abstract
We report a highly efficient perchloric acid catalyzed substitution reaction of 3-hydroxyoxindoles with thiols and alcohols for the synthesis of 3-substituted 3-(alkylthio)oxindoles or 3-alkoxyoxindoles, with catalyst loading down to 0.5 mol%. The scope and limitation of this method has been studied. An unprecedented mercury(II) perchlorate trihydrate catalyzed tandem Sakurai-Hosomi/(thio)ether formation reaction, starting from isatins, allyltrimethylsilane, and thiols or alcohols, has also been developed, which enables the facile synthesis of versatile 3-(alkylthio)- or 3-alkoxy-3- allyloxindoles.
| Original language | English |
|---|---|
| Article number | SS-2012-E0588-FA |
| Pages (from-to) | 3129-3144 |
| Number of pages | 16 |
| Journal | Synthesis (Germany) |
| Volume | 44 |
| Issue number | 20 |
| DOIs | |
| State | Published - 2012 |
Keywords
- 3-(alkylthio)oxindoles
- 3-alkoxyoxindoles
- 3-hydroxyoxindoles
- atom-efficient
- tandem reaction