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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 40, 2010 - Issue 22
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Original Articles

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

, , , , &
Pages 3309-3314 | Received 14 Sep 2008, Published online: 15 Oct 2010
 

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.

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.

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