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Anodic Dehydrogenative Cyanamidation of Thioethers: Simple and Sustainable Synthesis of <i>N</i>‐Cyanosulfilimines

Martin Klein, Siegfried R. Waldvogel

2021Angewandte Chemie International Edition32 citationsDOIOpen Access PDF

Abstract

A novel and very simple to perform electrochemical approach for the synthesis of several N-cyanosulfilimines in good to excellent yields was established. This method provides access to biologically relevant sulfoximines by consecutive oxidation using electro-generated periodate. This route can be easily scaled-up to gram quantities. The S,N coupling is carried out at an inexpensive carbon anode by direct oxidation of sulfide. Therefore, the designed process is atom economic and represents a new "green route" for the synthesis of sulfilimines and sulfoximines.

Topics & Concepts

PeriodateAnodeElectrochemistrySimple (philosophy)SulfideCombinatorial chemistryAtom (system on chip)ChemistryCoupling (piping)Computer scienceMaterials scienceOrganic chemistryMetallurgyElectrodeEmbedded systemPhysical chemistryPhilosophyEpistemologySulfur-Based Synthesis TechniquesRadical Photochemical ReactionsSynthesis and Catalytic Reactions
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