Iodonium Salt‐Mediated Oxidation of Sulfides to Sulfoxides by DMSO

Iodonium Salt‐Mediated Oxidation of Sulfides to Sulfoxides by DMSO

Compounds bearing the sulfoxide moiety display an important class of molecules in pharmaceutical industry. Many efforts have been made towards the development of novel, sustainable, easy‐to‐execute and industrially friendly processes. A novel iodonium‐salt‐mediated oxidation protocol for the convers...

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Bibliographic Details
Published in:European journal of organic chemistry Vol. 27; no. 38
Main Authors: Avramidou, Elisavet, Triandafyllou, Agapi K., Zisopoulou, Stavroula A., Stini, Naya A., Demertzidou, Vera P., Kokotos, Christoforos G., Gkizis, Petros L., Gallos, John K.
Format: Journal Article
Language:English
Published: Weinheim Wiley Subscription Services, Inc 07-10-2024
Subjects:
APIs
DMSO
Functional groups
Industrial development
Iodonium salts
Oxidation
Oxidizing agents
Pharmaceuticals
Sulfides
Sulfoxides
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Summary:Compounds bearing the sulfoxide moiety display an important class of molecules in pharmaceutical industry. Many efforts have been made towards the development of novel, sustainable, easy‐to‐execute and industrially friendly processes. A novel iodonium‐salt‐mediated oxidation protocol for the conversion of sulfides into the corresponding sulfoxides is reported, employing DMSO as the oxidant. Several sulfides decorated with various functional groups were tested, leading to the corresponding products in good to excellent yields with remarkable chemoselectivity. The oxidation protocol was successfully applied to the synthesis of the pharmaceutical active ingredients (APIs) Sulforaphane and Modafinil. A novel iodonium salt mediated methodology activating sulfur atom, promoting the conversion of sulfides into sulfoxides exploiting DMSO as the sole oxidant. An easy access to pharmaceutical active compounds such as Sulforaphane and Modafinil.
Bibliography:Denotes equal contribution
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202400596