A Mild and Highly Efficient Oxidation of Sulfides to Sulfoxides with Periodic Acid Catalyzed by FeCl3
Sung Soo Kim*, Kasi Nehru, Sang Soo Kim, Dong Won Kim, Hyun Chul Jung
*Department of Chemistry and Center for Chemical Dynamics, Inha University,
Incheon 402-751, South Korea,
Email: sungsoo
inha.ac.kr
S. S. Kim, K. Nehru, S. S. Kim, D. W. Kim, H. C. Jung, Synthesis, 2002, 2484-2486.
DOI: 10.1055/s-2002-35623
Abstract
An excellent method for the selective oxidation of sulfides to sulfoxides with periodic acid (H5IO6) catalyzed by FeCl3 in MeCN has been devised. The reported procedure is fast, simple and the yields are excellent in most cases with reaction time of less than 2 minutes.
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Details
The document presents a highly efficient method for the selective oxidation of sulfides to sulfoxides using periodic acid (H5IO6) catalyzed by iron chloride (FeCl3) in acetonitrile (MeCN). This method is notable for its simplicity, speed, and high yields, often exceeding 98% within less than 2 minutes. The study highlights the catalytic effect of FeCl3, which significantly reduces the reaction time compared to using H5IO6 alone. Various sulfides, including substituted thioanisoles and linear dialkyl sulfides, were tested, showing excellent yields and minimal influence from electronic and steric effects. The oxidation mechanism likely involves the formation of a hypervalent Fe(V)=O species that transfers oxygen to the sulfide. The procedure involves dissolving FeCl3 and the sulfide in MeCN, adding H5IO6, and monitoring the reaction by TLC. The products are purified by column chromatography and identified by NMR and GC-MS. This method is considered outstanding due to its efficiency and high yield, making it a valuable contribution to organic synthesis. The research was supported by the Korea Science and Engineering Foundation and dedicated to the memory of Professor Sang Chul Shim.
Key Words
sulfides, sulfoxides, periodic acid, iron chloride, hypervalent
ID: J66-Y2002-1680
