ArticleJournal of the American Chemical Society2020
Sulfonate Versus Sulfonate: Nickel and Palladium Multimetallic Cross-Electrophile Coupling of Aryl Triflates with Aryl Tosylates.
Article in Journal of the American Chemical Society, 2020. 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
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
25 citing papers in PubMed, 119 citations in OpenAlex.
- A General Approach toJournal of the American Chemical Society · 2026Article
- Cobalt-catalyzed reductive cross-coupling: a review.Molecular diversity · 2025Review
- Predictable C-H Functionalization of ComplexACS central science · 2025Article
- Reductively Induced Aryl Transmetalation: An Alternative Catalytically Relevant Ni-Catalyzed Biaryl Coupling Mechanism.Journal of the American Chemical Society · 2025Article
- Late-Stage Cross-Electrophile Coupling of Arylthianthrenium Salts with (Hetero)aryl (Pseudo)halides via Palladium Catalysis.Angewandte Chemie (International ed. in English) · 2025Article
- Easily Accessible and Solution-Stable Ni(0) Precatalysts for High-Throughput Experimentation.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
- Selective Ni-Catalyzed Cross-Electrophile Coupling of Heteroaryl Chlorides and Aryl Bromides at 1:1 Substrate Ratio.Journal of the American Chemical Society · 2025Article
- Cross-Electrophile Coupling: Principles, Methods, and Applications in Synthesis.Chemical reviews · 2024Review
- Zinc and manganese redox potentials in organic solvents and their influence on nickel-catalysed cross-electrophile coupling.Nature chemistry · 2024Article
- Kinetics and Mechanism of PPhJournal of the American Chemical Society · 2024Article
- Nickel-Catalyzed Atroposelective Cross-Electrophile Coupling of Aryl Halides: A General and Practical Route to Diverse MOP-Type Ligands.Journal of the American Chemical Society · 2024Article
- Cobalt-catalyzed cross-electrophile coupling of alkynyl sulfides with unactivated chlorosilanes.Nature communications · 2024Article
- Deep Electroreductive Chemistry: Harnessing Carbon- and Silicon-based Reactive Intermediates in Organic Synthesis.ACS catalysis · 2023Article
- Stereospecific Nickel-Catalyzed Cross-Electrophile Coupling Reaction of Alkyl Mesylates and Allylic Difluorides to Access Enantioenriched Vinyl Fluoride-Substituted Cyclopropanes.ACS catalysis · 2023Article
- Protodemetalation of (Bipyridyl)Ni(II)-Aryl Complexes Shows Evidence for Five-, Six-, and Seven-Membered Cyclic Pathways.Journal of the American Chemical Society · 2023Article
- Multimetallic-Catalyzed C-C Bond-Forming Reactions: From Serendipity to Strategy.Journal of the American Chemical Society · 2023Review
- Ni- and Ni/Pd-Catalyzed Reductive Coupling of Lignin-Derived Aromatics to Access Biobased Plasticizers.ACS central science · 2023Article
- Electrosynthetic C-O Bond Activation in Alcohols and Alcohol Derivatives.Angewandte Chemie (International ed. in English) · 2023Review
- Nickel-catalyzed cross-electrophile allylation of vinyl bromides and the modification of anti-tumour natural medicine β-elemene.Chemical science · 2022Article
- Synergistic Catalyst-Mediator Pairings for Electroreductive Cross-Electrophile Coupling Reactions.ACS catalysis · 2022Article
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 at 2 institutions in 2 countries.
Funding
Abstract
While phenols are frequent and convenient aryl sources in cross-coupling, typically as sulfonate esters, the direct cross-Ullmann coupling of two different sulfonate esters is unknown. We report here a general solution to this challenge catalyzed by a combination of Ni and Pd with Zn reductant and LiBr as an additive. The reaction has broad scope, as demonstrated in 33 examples (65% ± 11% average yield). Mechanistic studies show that Pd strongly prefers the aryl triflate, the Ni catalyst has a small preference for the aryl tosylate, aryl transfer between catalysts is mediated by Zn, and Pd improves yields by consuming arylzinc intermediates.
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.