ReviewMolecules (Basel, Switzerland)2023
Synthesis of Sulfoximines and Sulfonimidamides Using Hypervalent Iodine Mediated NH Transfer.
Review in Molecules (Basel, Switzerland), 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.
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Who cites it
12 citing papers in PubMed.
- Mild Transsulfinamidation Enables Rapid Access to Sulfinamides, Sulfonamides, and Sulfonimidamides.Organic letters · 2026Article
- Sulfinylnitrenes via Chemoselective S-N Bond Cleavage: Design, Synthesis, and Applications.Organic letters · 2026Article
- Synthesis of new sulfoximines and sulfonimidamides derivatives as NKCC1 inhibitors.Frontiers in chemistry · 2026Article
- Direct Activation of Sulfides by C-H Oxidation with Photoexcited Nitroarenes: Formal Manipulations of the C─S Bond.Angewandte Chemie (International ed. in English) · 2025Article
- Chemoselective Electrochemical Coupling of Thioethers and Primary Amines for Accessing Sulfilimines and Sulfoximines.Journal of the American Chemical Society · 2025Article
- Sulfilimines: An Underexplored Bioisostere for Drug Design?Journal of medicinal chemistry · 2025Article
- Recent Progress in Synthetic Applications of Hypervalent Iodine(III) Reagents.Chemical reviews · 2024Review
- Strategies for oxidative synthesis ofRSC advances · 2024Article
- Strain-release driven reactivity of a chiral SuFEx reagent provides stereocontrolled access to sulfinamides, sulfonimidamides, and sulfoximines.Nature communications · 2024Article
- Azasulfur(iv) derivatives of sulfite and sulfinate esters by formal S-S bond insertion of dichloramines.Chemical science · 2024Article
- Sulfur stereochemistry takes centre stage.Nature chemistry · 2024Article
- Asymmetric synthesis of sulfoximines, sulfonimidoyl fluorides and sulfonimidamides enabled by an enantiopure bifunctional S(VI) reagent.Nature chemistry · 2024Article
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Authors and funding
2 authors.
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Abstract
The development of NH transfer reactions using hypervalent iodine and simple sources of ammonia has facilitated the synthesis of sulfoximines and sulfonimidamides for applications across the chemical sciences. Perhaps most notably, the methods have been widely applied in medicinal chemistry and in the preparation of biologically active compounds, including in the large-scale preparation of an API intermediate. This review provides an overview of the development of these synthetic methods involving an intermediate iodonitrene since our initial report in 2016 on the conversion of sulfoxides into sulfoximines. This review covers the NH transfer to sulfoxides and sulfinamides, and the simultaneous NH/O transfer to sulfides and sulfenamides to form sulfoximines and sulfonimidamides, respectively. The mechanism of the reactions and the identification of key intermediates are discussed. Developments in the choice of reagents, and in the reaction conditions and setups used are described.
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