ArticleNature communications2019
Practical and stereoselective electrocatalytic 1,2-diamination of alkenes.
Article in Nature communications, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 13 papers.
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13 citing papers in PubMed, 132 citations in OpenAlex.
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- Wireless Electrochemical Reactor for Accelerated Exploratory Study of Electroorganic Synthesis.ACS central science · 2023Article
- Modular and practical diamination of allenes.Nature communications · 2023Article
- Synthesis of Unsymmetrical Vicinal Diamines via Directed Hydroamination.Organic letters · 2022Article
- Photons or Electrons? A Critical Comparison of Electrochemistry and Photoredox Catalysis for Organic Synthesis.Chemical reviews · 2022Review
- Redox-active molecules as organocatalysts for selective oxidative transformations - an unperceived organocatalysis field.Beilstein journal of organic chemistry · 2022Article
- Electrochemical C-C bond cleavage of cyclopropanes towards the synthesis of 1,3-difunctionalized molecules.Nature communications · 2021Article
- Electrochemically driven stereoselective approach toChemical science · 2021Article
- Electroreductive Carbofunctionalization of Alkenes with Alkyl Bromides via a Radical-Polar Crossover Mechanism.Journal of the American Chemical Society · 2020Article
- Photoinduced Olefin Diamination with Alkylamines.Angewandte Chemie (International ed. in English) · 2020Article
- Enantiospecific electrochemical rearrangement for the synthesis of hindered triazolopyridinone derivatives.Nature communications · 2020Article
- Distinctive reactivity ofBeilstein journal of organic chemistry · 2020Article
Corrections and comments
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The 1,2-diamine motif is widely present in natural products, pharmaceutical compounds, and catalysts used in asymmetric synthesis. The simultaneous introduction of two amino groups across an alkene feedstock is an appealing yet challenging approach for the synthesis of 1,2-diamines, primarily due to the inhibitory effect of the diamine products to transition metal catalysts and the difficulty in controlling reaction diastereoselectivity and regioselectivity. Herein we report a scalable electrocatalytic 1,2-diamination reaction that can be used to convert stable, easily available aryl alkenes and sulfamides to 1,2-diamines with excellent diastereoselectivity. Monosubstituted sulfamides react in a regioselective manner to afford 1,2-diamines bearing different substituents on the two amino groups. The combination of an organic redox catalyst and electricity not only obviates the use of any transition metal catalyst and oxidizing reagent, but also ensures broad reaction compatibility with a variety of electronically and sterically diverse substrates.
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