ArticleNature chemistry2024
A general alkene aminoarylation enabled by N-centred radical reactivity of sulfinamides.
Article in Nature chemistry, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 26 papers.
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Who cites it
26 citing papers in PubMed.
- A radical-polar crossover approach to complex nitrogen heterocycles via the triplet state.Chem · 2026Article
- Remote 1,5-Difunctionalization of Alkenes via a Sulfinyl-Smiles Rearrangement and Vinylcyclopropane Ring-Opening Cascade.JACS Au · 2026Article
- High-Fidelity Transfer of Chiral Sulfonimidoyl Radicals.Journal of the American Chemical Society · 2026Article
- Radical docking-migration: a powerful strategy for difunctionalization of alkenes and alkynes.Chemical science · 2026Review
- Photocatalytic Aminoarylation of Styrenes.Organic letters · 2026Article
- Article
- Engineering of Integral Membrane Metalloenzyme UndB and Designing of a Cell-Free Biocatalytic Platform Enabled Efficient 1‑Alkene Production.ACS central science · 2025Article
- Article
- Copper-Catalyzed Asymmetric Cyclizative Sulfinamidation: Forging Indole-Based Stereogenic Sulfur(IV) Centers and Atropisomeric Chirality.ACS central science · 2025Article
- Smiles-Truce Cascades Enable Heteroaryl Cyclopropane and Sultine Synthesis.Angewandte Chemie (International ed. in English) · 2025Article
- Advancing Sulfinyl Radical Chemistry: An Asymmetric Smiles Rearrangement with Chiral Sulfoxides.Angewandte Chemie (International ed. in English) · 2025Article
- Harnessing Bifunctional N-Benzoyloxyamides for Photoredox Amidative Dual Functionalizations of Alkenes.Angewandte Chemie (International ed. in English) · 2025Article
- Merging Hydrogen-Atom-Transfer and the Truce-Smiles Rearrangement for Synthesis of β-Arylethylamines from Unactivated Allylsulfonamides.Angewandte Chemie (International ed. in English) · 2025Article
- Transition Metal Catalysis for the Asymmetric Synthesis of 2-Arylethylamines: A Review of the New Millennium.Molecules (Basel, Switzerland) · 2025Review
- Catalytic Enantioselective Smiles Rearrangement Enabled by the Directed Evolution of P450 Radical Aryl Migratases.Journal of the American Chemical Society · 2025Article
- Asymmetric reductive arylation and alkenylation to access S-chirogenic sulfinamides.Nature communications · 2025Article
- A General Amino-(Hetero)arylation of Simple Olefins with (Hetero)aryl Sulfonamides Enabled by anACS catalysis · 2025Article
- Merging SOMO activation with transition metal catalysis: Deoxygenative functionalization of amides to β-aryl amines.Science advances · 2025Article
- Reductive sulfinylation by nucleophilic chain isomerization of sulfonylpyridinium.Nature communications · 2025Article
- General Alkene 1,2-Journal of the American Chemical Society · 2024Article
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4 authors.
Funding
Abstract
Arylethylamines are popular structural elements in bioactive molecules but are often made through a linear series of synthetic steps. A modular protocol to assemble arylethylamines from alkenes in one step would represent a useful advance in discovery chemistry, though current limitations preclude a generally applicable method. In this work we disclose an aminoarylation of alkenes using aryl sulfinamide reagents as bifunctional amine and arene donors. This reaction features excellent regioselectivity and diastereoselectivity on a variety of activated and unactivated substrates. Using a weakly oxidizing photocatalyst, a nitrogen radical is generated under mild conditions and adds to an alkene to form a new C-N bond. A desulfinylative aryl migration event known as a Smiles-Truce rearrangement follows to form a new C-C bond. In this manner, arylethylamines can be rapidly assembled from abundant alkene feedstocks. Moreover, chiral information from the sulfinamide can be transferred via rearrangement to a new carbon stereocentre in the product, thus advancing the development of traceless asymmetric alkene difunctionalization.
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Registered trials
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