Air-Stable, Cationic, Lewis Acid, Titanocene Perfluorooctanesulfonate–Catalyzed Reductive Cleavage of S–S Bond by Zinc and Its Application in Synthesis of Thioesters

Abstract

Titanocene perfluorooctanesulfonate is air-stable complex. In the presence of 10 mol% of the complex, reductive cleavage of an S–S bond by zinc in commercial tetrahydrofuran at room temperature led to nucleophilic sulfur anion species, which reacted with acid anhydrides to afford thioesters in good to excellent yields.

Keywords:

• Disulfide
• thioester
• titanocene bis(perfluorooctanesulfonate)s
• zinc

ACKNOWLEDGMENTS

This work was supported by the National Nature Science Foundation of China (20372020). The authors thank the chief scientist of the “985” Project of Hunan University and Prof. Dr. Junzo Otera, and Prof. Dr. Akihiro Orita of Okayama University of Science for their helpful supervision and discussion.