Sulfur–Sulfur Bond-Driven Synthesis of 3-Thiooxindoles Using Triflic Acid without a Metal or Hydride Source
Abstract
A triflic acid-catalyzed, metal-free protocol has been developed for the synthesis of 3-thiooxindoles from readily available isatin and thiophenol derivatives under mild conditions, thereby avoiding the use of fluorinated solvents, silanes, and additives. The method exhibits a broad substrate scope with moderate to good yields. In addition, the strategy enables thioether formation from ketones via 3,3-bis(aryl/alkylthio) indolinone, highlighting mechanistic versatility in an acidic medium. Experimental evidence from intermediate and mechanistic investigations substantiates the reaction pathway. Further derivatizations led to antimicrobial compound II, demonstrating synthetic utility.
Fields of Study & Subjects
Sulfur-Based Synthesis Techniques
Synthesis and Reactivity of Sulfur-Containing Compounds
Synthesis of Indole Derivatives
Publication details
- Journal / source
- The Journal of Organic Chemistry
- Volume
- 91
- Issue
- 3
- Pages
- 1412–1421
- Publication date
- 12 January 2026
- Language
- EN