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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:,

K. Bahrami, M. M. Khodaei, A. Karimi, Synthesis, 2008, 2543-2546.

DOI: 10.1055/s-2008-1067190


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.

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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