Evidence map›Paper›PMID 38188282›Full record

ArticleACS catalysis2023

Nickel-Catalyzed Electroreductive Coupling of Alkylpyridinium Salts and Aryl Halides.

Jiantao Fu, Windsor Lundy, Rajdip Chowdhury, J Cameron Twitty, Long P Dinh, Jessica Sampson, Yu-Hong Lam, Christo S Sevov, Mary P Watson, Dipannita Kalyani

Abstract read
In one paragraph

Article in ACS catalysis, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 14 papers.

0numbers the graph read from it
0cells of the map it votes in
14citing 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

14 citing papers in PubMed.

  1. Review
  2. Review
  3. Article
  4. Article
  5. Article
  6. Cross-Electrophile Coupling ofJournal of the American Chemical Society · 2026
    Article
  7. Article
  8. Review
  9. Review
  10. Article
  11. CspACS catalysis · 2024
    Article
  12. Article
  13. Review
  14. PrimaryFaraday discussions · 2023
    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

10 authors.

Jiantao FuDiscovery Chemistry, Merck & Co., Inc., Kenilworth, New Jersey 07033, United States.
Windsor LundyDepartment of Chemistry & Biochemistry, University of Delaware, Newark, Delaware 19716, United States.
Rajdip ChowdhuryDepartment of Chemistry & Biochemistry, The Ohio State University, Columbus, Ohio 43210, United States.
J Cameron TwittyDepartment of Chemistry & Biochemistry, University of Delaware, Newark, Delaware 19716, United States.
Long P DinhDepartment of Chemistry & Biochemistry, The Ohio State University, Columbus, Ohio 43210, United States.
Jessica SampsonHigh Throughput Experimentation Facility, Department of Chemistry & Biochemistry, University of Delaware, Newark, Delaware 19716, United States.
Yu-Hong LamModeling & Informatics, Merck & Co., Inc., Rahway, New Jersey 07065, United States.
Christo S SevovDepartment of Chemistry & Biochemistry, The Ohio State University, Columbus, Ohio 43210, United States.
Mary P WatsonDepartment of Chemistry & Biochemistry, University of Delaware, Newark, Delaware 19716, United States.
Dipannita KalyaniDiscovery Chemistry, Merck & Co., Inc., Kenilworth, New Jersey 07033, United States.

Funding

This renovation project will create over 1455 sq. ft. of state- of-the-art reseaP20GM104316 · NIGMS · UNIVERSITY OF DELAWARE · PI FOX, JOSEPH M · 2014 to 2024
$26.8M
Chemistry-Biology Interface Predoctoral Training Grant 2024-2029T32GM133395 · NIGMS · UNIVERSITY OF DELAWARE · PI Catherine Leimkuhler Grimes · 2019 to 2026
$3.7M
Supplement to Harnessing Alkyl Amines and Alkyl Alcohols in Cross-CouplingR35GM131816 · NIGMS · UNIVERSITY OF DELAWARE · PI Mary P Watson · 2019 to 2026
$3.4M
Late-stage C-H functionalization and C-C/N coupling enabled by new strategies for electrochemically-controlled radical formationR35GM138373 · NIGMS · OHIO STATE UNIVERSITY · PI Christo Sevov · 2020 to 2026
$2.3M
Molecular Design of Advanced BiomaterialsP20GM103541 · NIGMS · UNIVERSITY OF DELAWARE · PI POLENOVA, TATYANA · 2012 to 2012
$2.1M
Q-Exactive Orbitrap LC-MC/MS SystemS10OD016267 · OD · UNIVERSITY OF DELAWARE · PI JOHNSTON, MURRAY V · 2013 to 2013
$573k
NIGMS NIH HHS P20 GM103541NIGMS NIH HHS P20 GM104316NIGMS NIH HHS R35 GM131816NIGMS NIH HHS R35 GM138373NIGMS NIH HHS T32 GM133395NIH HHS S10 OD016267
6 · The paper itself

Abstract

An electrochemical, nickel-catalyzed reductive coupling of alkylpyridinium salts and aryl halides is reported. High-throughput experimentation (HTE) was employed for rapid reaction optimization and evaluation of a broad scope of pharmaceutically relevant structurally diverse aryl halides, including complex drug-like substrates. In addition, the transformation is compatible with both primary and secondary alkylpyridinium salts with distinct conditions. Mechanistic insights were critical to enhance the efficiency of coupling using secondary alkylpyridinium salts. Systematic comparisons of the electrochemical and non-electrochemical methods revealed the complementary scope and efficiency of the two approaches.

Indexed as

deaminationelectrochemistryhigh-throughput experimentationNickel catalysispharmaceutical discoveryreductive cross-electrophile coupling

Identifiers

PMID38188282
PMCPMC10769313

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.