Evidence map›Paper›PMID 33628617›Full record

ArticleACS catalysis2020

A Widely Applicable Dual Catalytic System for Cross-Electrophile Coupling Enabled by Mechanistic Studies.

David J Charboneau, Emily L Barth, Nilay Hazari, Mycah R Uehling, Susan L Zultanski

Abstract read
In one paragraph

Article in ACS catalysis, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 27 papers.

0numbers the graph read from it
0cells of the map it votes in
27citing 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

27 citing papers in PubMed.

  1. Review
  2. Review
  3. Article
  4. Article
  5. Cross-Electrophile Coupling ofJournal of the American Chemical Society · 2026
    Article
  6. Article
  7. Article
  8. Review
  9. Review
  10. Article
  11. Cross-Electrophile Coupling to Form Sterically Hindered C(spJournal of the American Chemical Society · 2025
    Article
  12. Review
  13. Article
  14. Article
  15. Formal Cross-Coupling of Amines and Carboxylic Acids to Form spJournal of the American Chemical Society · 2023
    Article
  16. High-Throughput Photo- and Electrochemical spACS medicinal chemistry letters · 2023
    Article
  17. Review
  18. Article
  19. Review
  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

5 authors.

David J CharboneauDepartment of Chemistry, Yale University, New Haven, Connecticut 06520, United States.
Emily L BarthDepartment of Chemistry, Yale University, New Haven, Connecticut 06520, United States.
Nilay HazariDepartment of Chemistry, Yale University, New Haven, Connecticut 06520, United States.ORCID 0000-0001-8337-198X
Mycah R UehlingMerck & Co., Inc., Discovery Chemistry, HTE and Lead Discovery Capabilities, Kenilworth, New Jersey 07033, United States.
Susan L ZultanskiMerck & Co., Inc., Department of Process Research and Development, Rahway, New Jersey 07065, United States.

Funding

Mechanistic Studies to Rationally Design Ni and Pd Catalysts for Cross-CouplingR01GM120162 · NIGMS · YALE UNIVERSITY · PI HAZARI, NILAY · 2016 to 2020
$1.6M
NIGMS NIH HHS R01 GM120162
6 · The paper itself

Abstract

A dual catalytic system for cross-electrophile coupling reactions between aryl halides and alkyl halides that features a Ni catalyst, a Co cocatalyst, and a mild homogeneous reductant is described. Mechanistic studies indicate that the Ni catalyst activates the aryl halide, while the Co cocatalyst activates the alkyl halide. This allows the system to be rationally optimized for a variety of substrate classes by simply modifying the loadings of the Ni and Co catalysts based on the reaction product profile. For example, the coupling of aryl bromides and aryl iodides with alkyl bromides, alkyl iodides, and benzyl chlorides is demonstrated using the same Ni and Co catalysts under similar reaction conditions but with different optimal catalyst loadings in each case. Our system is tolerant of numerous functional groups and is capable of coupling heteroaryl halides, di-

Indexed as

cross-electrophile couplingmechanismmedicinal chemistrynickelsynthetic methods

Identifiers

PMID33628617
PMCPMC7899151

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Registered trials

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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.