Evidence map›Paper›PMID 32412241›Full record

ArticleJournal of the American Chemical Society2020

Nickel-Catalyzed Cross-Electrophile Coupling of Aryl Chlorides with Primary Alkyl Chlorides.

Seoyoung Kim, Matthew J Goldfogel, Michael M Gilbert, Daniel J Weix

Abstract read
In one paragraph

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 46 papers.

0numbers the graph read from it
0cells of the map it votes in
46citing papers in PubMed
–field-weighted citation impact
1 · What the graph read from it

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.

2 · The registry

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.

3 · Its place in the literature

Who cites it

46 citing papers in PubMed.

  1. Article
  2. Article
  3. Nickel-Catalyzed Radical-Radical Cross-Coupling Reactions.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026
    Review
  4. Ring-opening decarbonylative C(spChemical science · 2026
    Article
  5. Article
  6. Article
  7. Article
  8. Aryl Acid-Alcohol Cross-Coupling: C(spJournal of the American Chemical Society · 2025
    Article
  9. Article
  10. Article
  11. Article
  12. Article
  13. Review
  14. Regiodivergent Radical-Relay Alkene Dicarbofunctionalization.Journal of the American Chemical Society · 2024
    Article
  15. Article
  16. Article
  17. Article
  18. Article
  19. Article
  20. Article
4 · The record

Corrections and comments

PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.

5 · Who and what money

Authors and funding

4 authors.

Seoyoung KimDepartment of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, Wisconsin 53706, United States.
Matthew J GoldfogelDepartment of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, Wisconsin 53706, United States.ORCID 0000-0002-6911-3068
Michael M GilbertDepartment of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, Wisconsin 53706, United States.
Daniel J WeixDepartment of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, Wisconsin 53706, United States.ORCID 0000-0002-9552-3378

Funding

Reductive Coupling Reactions: Trading Organometallic Reagents for Organic HalidesR01GM097243 · NIGMS · UNIVERSITY OF WISCONSIN-MADISON · PI Daniel John Weix · 2011 to 2026
$5.6M
QExactive (Orbitrap) mass spectrometerS10OD020022 · OD · UNIVERSITY OF WISCONSIN-MADISON · PI VESTLING, MARTHA M · 2015 to 2015
$483k
Pairing Alkyl Radicals with Ni Catalysts: Elucidating Mechanism and Exploring New Reaction Methodology with CarboxylatesF32GM122362 · NIGMS · UNIVERSITY OF WISCONSIN-MADISON · PI GOLDFOGEL, MATTHEW JACOB · 2017 to 2017
$57k
NIGMS NIH HHS F32 GM122362NIGMS NIH HHS R01 GM097243NIH HHS S10 OD020022
6 · The paper itself

Abstract

Alkyl chlorides and aryl chlorides are among the most abundant and stable carbon electrophiles. Although their coupling with carbon nucleophiles is well developed, the cross-electrophile coupling of aryl chlorides with alkyl chlorides has remained a challenge. We report here the first general approach to this transformation. The key to productive, selective cross-coupling is the use of a small amount of iodide or bromide along with a recently reported ligand, pyridine-2,6-bis(

Indexed as

Hydrocarbons, ChlorinatedCatalysisMolecular StructureNickelHydrocarbons, ChlorinatedNickel

Identifiers

PMID32412241
PMCPMC7418462

What OpenQuestion holds

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Registered trials

None linked

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.