ArticleJournal of the American Chemical Society2017
Transition-Metal-Free Radical C(sp
Article in Journal of the American Chemical Society, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 25 papers.
What it found
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
The trial behind it
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Who cites it
25 citing papers in PubMed, 111 citations in OpenAlex.
- α-C-H Functionalization of Benzylamines: A Crucial Yet Challenging Transformation.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Review
- Synthetic Applications of Hydroxamic Acids and Their Derivatives in Organic Chemistry.ACS organic & inorganic Au · 2026Review
- Acyl-oxyallenes as α,β-unsaturated ketone surrogates for Giese radical addition.Chemical science · 2026Article
- Iodoarene Activation: Take a Leap Forward toward Green and Sustainable Transformations.Chemical reviews · 2025Review
- Dual NHC/HAT-Promoted Esterification to Access α-Aryl Glycines.Advanced synthesis & catalysis · 2025Article
- Efficient construction of functionalized pyrroloindolines through cascade radical cyclization/intermolecular coupling.Chemical science · 2024Article
- C-F bond activation enables synthesis of aryl difluoromethyl bicyclopentanes as benzophenone-type bioisosteres.Nature communications · 2024Article
- Net-1,2-Hydrogen Atom Transfer of Amidyl Radicals: Toward the Synthesis of 1,2-Diamine Derivatives.Journal of the American Chemical Society · 2023Article
- Intermolecular Hydroalkoxylation and Hydrocarboxylation of 2-Azadienes with High Efficiency.The Journal of organic chemistry · 2023Article
- α-Branched amines through radical coupling with 2-azaallyl anions, redox active esters and alkenes.Chemical science · 2022Article
- SET activation of nitroarenes by 2-azaallyl anions as a straightforward access to 2,5-dihydro-1,2,4-oxadiazoles.Nature communications · 2021Article
- Cobalt and Iron Stabilized Ketyl, Ketiminyl and Aldiminyl Radical Anions.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- Lewis Basic Salt-Promoted Organosilane Coupling Reactions with Aromatic Electrophiles.Journal of the American Chemical Society · 2021Article
- Transition-metal-free allylation of 2-azaallyls with allyl ethers through polar and radical mechanisms.Nature communications · 2021Article
- Aryl radical-mediated N-heterocyclic carbene catalysis.Nature communications · 2021Article
- Design and Synthesis of Fluorescent 1,3-Diaryl-β-carbolines and 1,3-Diaryl-3,4-dihydro-β-carbolines.ACS omega · 2021Article
- Nickel-catalyzed enantioselective vinylation of aryl 2-azaallyl anions.Chemical science · 2021Article
- Excited State Anions in Organic Transformations.Angewandte Chemie (International ed. in English) · 2021Review
- Synthesis of an elusive, stable 2-azaallyl radical guided by electrochemical and reactivity studies of 2-azaallyl anions.Chemical science · 2021Article
- Transition-metal-free C(spChemical science · 2020Article
Corrections and comments
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Authors and funding
10 authors at 4 institutions in 3 countries.
Funding
Abstract
The past decade has witnessed the rapid development of radical generation strategies and their applications in C-C bond-forming reactions. Most of these processes require initiators, transition metal catalysts, or organometallic reagents. Herein, we report the discovery of a simple organic system (2-azaallyl anions) that enables radical coupling reactions under transition-metal-free conditions. Deprotonation of N-benzyl ketimines generates semistabilized 2-azaallyl anions that behave as "super-electron-donors" (SEDs) and reduce aryl iodides and alkyl halides to aryl and alkyl radicals. The SET process converts the 2-azaallyl anions into persistent 2-azaallyl radicals, which capture the aryl and alkyl radicals to form C-C bonds. The radical coupling of aryl and alkyl radicals with 2-azaallyl radicals makes possible the synthesis of functionalized amine derivatives without the use of exogenous radical initiators or transition metal catalysts. Radical clock studies and 2-azaallyl anion coupling studies provide mechanistic insight for this unique reactivity.
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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.