ArticleProceedings of the National Academy of Sciences of the United States of America2020
HARC as an open-shell strategy to bypass oxidative addition in Ullmann-Goldberg couplings.
Article in Proceedings of the National Academy of Sciences of the United States of America, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.
What it found
Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.
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
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.
Who cites it
12 citing papers in PubMed.
- A General Metallaphotoredox Platform forJournal of the American Chemical Society · 2025Article
- Discovery and Development of an Aerobic Radical Hydroxyarylation Reaction Using Aryl Halides, Olefins, and OOrganic letters · 2025Article
- Multicomponent Synthesis of α-Branched Amines via a Zinc-Mediated Carbonyl Alkylative Amination Reaction.Journal of the American Chemical Society · 2024Article
- Photoredox-Driven Three-Component Coupling of Aryl Halides, Olefins, and OACS catalysis · 2024Article
- Article
- Room-Temperature Copper-Mediated Radiocyanation of Aryldiazonium Salts and Aryl Iodides via Aryl Radical Intermediates.Journal of the American Chemical Society · 2023Article
- Exploiting the spNature chemistry · 2022Article
- Metallaphotoredox: The Merger of Photoredox and Transition Metal Catalysis.Chemical reviews · 2022Review
- A biomimetic SScience (New York, N.Y.) · 2021Article
- A GeneralChem · 2021Article
- Photoredox Catalyzed Dealkylative Aromatic Halogen Substitution with Tertiary Amines.Molecules (Basel, Switzerland) · 2021Article
- Metallaphotoredox Perfluoroalkylation of Organobromides.Journal of the American Chemical Society · 2020Article
Corrections and comments
PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.
Authors and funding
3 authors.
Funding
Abstract
The copper-catalyzed arylation of unsaturated nitrogen heterocycles, known as the Ullmann-Goldberg coupling, is a valuable transformation for medicinal chemists, providing a modular disconnection for the rapid diversification of heteroaromatic cores. The utility of the coupling, however, has established limitations arising from a high-barrier copper oxidative addition step, which often necessitates the use of electron-rich ligands, elevated temperatures, and/or activated aryl electrophiles. Herein, we present an alternative aryl halide activation strategy, in which the critical oxidative addition (OA) mechanism has been replaced by a halogen abstraction-radical capture (HARC) sequence that allows the generation of the same Cu(III)-aryl intermediate albeit via a photoredox pathway. This alternative mechanistic paradigm decouples the bond-breaking and bond-forming steps of the catalytic cycle to enable the use of many previously inert aryl bromides. Overall, this mechanism allows access to both traditional C-N adducts at room temperature as well as a large range of previously inaccessible Ullmann-Goldberg coupling products including sterically demanding
Indexed as
Identifiers
What OpenQuestion holds
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.