ArticleACS catalysis2022
Mechanism of Visible Light-Mediated Alkene Aminoarylation with Arylsulfonylacetamides.
Article in ACS catalysis, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 15 papers.
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Who cites it
15 citing papers in PubMed, 59 citations in OpenAlex.
- Article
- 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
- A General Amino-(Hetero)arylation of Simple Olefins with (Hetero)aryl Sulfonamides Enabled by anACS catalysis · 2025Article
- Harnessing Bromo/Acyloxy Transposition (BrAcT) and Excited-State Copper Catalysis for Styrene Difunctionalization.Journal of the American Chemical Society · 2024Article
- Radical-Mediated α-JACS Au · 2024Article
- A general alkene aminoarylation enabled by N-centred radical reactivity of sulfinamides.Nature chemistry · 2024Article
- Chiral arylsulfinylamides as reagents for visible light-mediated asymmetric alkene aminoarylations.Nature chemistry · 2024Article
- A free-radical design featuring an intramolecular migration for a synthetically versatile alkyl-(hetero)arylation of simple olefins.Chemical science · 2024Article
- Aryne-Enabled C-N Arylation of Anilines.Angewandte Chemie (International ed. in English) · 2023Article
- Synthesis of Functionalized Pyrrolidinone Scaffolds via Smiles-Truce Cascade.Organic letters · 2023Article
- An NHC-Catalyzed Desulfonylative Smiles Rearrangement of Pyrrole and Indole Carboxaldehydes.The Journal of organic chemistry · 2023Article
- Photoinduced Copper-Catalyzed Late-Stage Azidoarylation of Alkenes via Arylthianthrenium Salts.Journal of the American Chemical Society · 2023Article
Corrections and comments
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Authors and funding
6 authors at 2 institutions in 2 countries.
Funding
Abstract
Alkene aminoarylation with arylsulfonylacetamides via a visible-light mediated radical Smiles-Truce rearrangement represents a convenient approach to the privileged arylethylamine pharmacaphore traditionally generated by circuitous, multi-step sequences. Herein, we report detailed synthetic, spectroscopic, kinetic, and computational studies designed to interrogate the proposed mechanism, including the key aryl transfer event. The data are consistent with a rate-limiting 1,4-aryl migration occurring either via a stepwise process involving a radical Meisenheimer-like intermediate or in a concerted fashion dependent on both arene electronics and alkene sterics. Our efforts to probe the mechanism have significantly expanded the substrate scope of the transformation with respect to the migrating aryl group and provide further credence to the synthetic potential of radical aryl migrations.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.