Electrochemical oxidation chemoselective sulfimidation of thioether with sulfonamide via catalytic iodobenzene

• Published in: Tetrahedron letters Vol. 102; pp. 153925 - 153929
• Main Authors: Han, Min, Tang, Zhuo, Li, Guang-xun, Wang, Qi-wei
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 20.07.2022; Elsevier
• Subjects: Catalytic iodobenzene; Chemistry; Chemistry, Organic; Electrochemical oxidation; Physical Sciences; Science & Technology; Sulfilimine; Sulfonamide; Thioether; Thioether; Catalytic iodobenzene; Sulfonamide; Sulfilimine; Electrochemical oxidation; SULFOXIMINES; AZIDES; SULFIDES; NITRENE TRANSFER-REACTIONS; SULFOXIDES; AMINATION; ALKYLZINC; IMINATION; DERIVATIVES
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/j.tetlet.2022.153925

Herein we developed a useful method for the preparation of the desired sulfilimines with readily available sulfonamides as nitrogen sources and iodobenzene as the catalyst. The reaction proceeds via the in-situ produced hypervalent iodine from catalytic simple iodobenzene under electrooxidation conditions. This oxidative coupling strategy can be employed for a wide range of aromatic sulfide and sulfonamide. The obtained sulfilimines could be easily transformed to biologically important NH free sulfoximines in good yields. [Display omitted] Sulfilimines, the aza-analogs of sulfoxides, are valuable building blocks in organic synthesis and serve as important functional groups in medicinal chemistry. Herein we reported an efficient and environmentally friendly method of preparing sulfilimines from readily available thioether and sulfonamide as substrate. The reaction proceeds via the in-situ produced hypervalent iodine from catalytic simple iodobenzene under electrooxidation conditions. A series of sulfilimines were obtained in moderate to good yields.