Mild and Efficient Deoxygenation of Sulfoxides to Sulfides with Triflic Anhydride/Potassium Iodide Reagent System
Kiumars Bahrami*, Mohammad Mehdi Khodaei*, Ahmad Karimi
*Department of Chemistry, Razi University, Kermanshah 67149,
Iran, Email: kbahrami2
hotmail.com, mmkhodarazi.ac.ir
K. Bahrami, M. M. Khodaei, A. Karimi, Synthesis, 2008, 2543-2546.
DOI: 10.1055/s-2008-1067190
Abstract
The combination of triflic anhydride and potassium iodide was an effective promoter for the deoxygenation of sulfoxides and gave the corresponding sulfides in excellent yield in acetonitrile at room temperature. This reagent system is chemoselective and tolerates various functional groups, such as alkenes, ketones, esters, aldehydes, acids, and oximes.
see article for more examples
proposed mechanism
TAPC-Promoted Oxidation of Sulfides and Deoxygenation of Sulfoxides
K. Bahrami, M. M. Khodaei, M. S. Arabi, J. Org. Chem., 2010, 75, 6208-6213
Key Words
deoxygenation, sulfoxides, sulfides, chemoselective, triflic anhydride, potassium iodide
ID: J66-Y2008-2190
