ArticleNature chemistry2022
Bifunctional sulfilimines enable synthesis of multiple N-heterocycles from alkenes.
Article in Nature chemistry, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 14 papers.
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14 citing papers in PubMed.
- Base-Free C-N Cross-Electrophile Coupling.Journal of the American Chemical Society · 2026Article
- Sulfilimines Are Azide Alternatives for Nitrene-Mediated Aromatic C-to-N Transmutation.Journal of the American Chemical Society · 2026Article
- Radical Sampling Enabled Saturated N-Heterocycle Cyclization.Journal of the American Chemical Society · 2026Article
- Chemoselective Electrochemical Coupling of Thioethers and Primary Amines for Accessing Sulfilimines and Sulfoximines.Journal of the American Chemical Society · 2025Article
- Mechanism of EnT-mediated amino-sulfonylation of alkenes withRSC advances · 2025Article
- Photocatalytic Synthesis of Substituted 2-Aryl Morpholines via Diastereoselective Annulation.Journal of the American Chemical Society · 2025Article
- The Tribological Properties of Novel Sulfoximine Derivatives as Lubricant Additives.Materials (Basel, Switzerland) · 2024Article
- Thianthrene/TfOH-catalyzed electrophilic halogenations usingChemical science · 2024Article
- Copper-Catalyzed Three-Component Synthesis of Highly Substituted Morpholines.Organic letters · 2024Article
- High-throughput synthesis provides data for predicting molecular properties and reaction success.Science advances · 2023Article
- Tunable [3+2] and [4+2] annulations for pyrrolidine and piperidine synthesis.Chemical communications (Cambridge, England) · 2023Article
- Article
- Radical Redox Annulations: A General Light-Driven Method for the Synthesis of Saturated Heterocycles.ACS catalysis · 2022Article
- Radical ring formation.Nature chemistry · 2022Article
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Abstract
Intramolecular cyclization of nitrogen-containing molecules onto pendant alkenes is an efficient strategy for the construction of N-heterocycles, which are of paramount importance in, for example, pharmaceuticals and materials. Similar intermolecular cyclization reactions, however, are scarcer for nitrogen building blocks, including N-centred radicals, and divergent and modular versions are not established. Here we report the use of sulfilimines as bifunctional N-radical precursors for cyclization reactions with alkenes to produce N-unprotected heterocycles in a single step through photoredox catalysis. Structurally diverse sulfilimines can be synthesized in a single step, and subsequently engage with alkenes to afford synthetically valuable five-, six- and seven-membered heterocycles. The broad and diverse scope is achievable by a radical-polar crossover annulation enabled by the bifunctional character of the reagents, which distinguishes itself from all other N-centred-radical-based reactions. The modular synthesis of the sulfilimines allows for larger structural diversity of N-heterocycle products than is currently achievable with other single cyclization methods.
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