Evidence map›Paper›PMID 30917282›Full record

ArticleOrganic letters2019

Deaminative Reductive Cross-Electrophile Couplings of Alkylpyridinium Salts and Aryl Bromides.

Jennie Liao, Corey H Basch, Megan E Hoerrner, Michael R Talley, Brian P Boscoe, Joseph W Tucker, Michelle R Garnsey, Mary P Watson

Abstract read
In one paragraph

Article in Organic letters, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 44 papers.

0numbers the graph read from it
0cells of the map it votes in
44citing 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

44 citing papers in PubMed.

  1. Review
  2. Article
  3. Deaminative C(Journal of the American Chemical Society · 2026
    Article
  4. Angewandte Chemie (International ed. in English) · 2026
    Article
  5. Article
  6. Article
  7. Low-energy photoredox catalysis.Nature reviews. Chemistry · 2025
    Review
  8. Review
  9. Article
  10. Article
  11. Article
  12. Article
  13. Article
  14. Article
  15. Article
  16. PrimaryFaraday discussions · 2023
    Article
  17. Review
  18. Article
  19. Formal Cross-Coupling of Amines and Carboxylic Acids to Form spJournal of the American Chemical Society · 2023
    Article
  20. Formation of C(spJournal of the American Chemical Society · 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

8 authors.

Jennie LiaoDepartment of Chemistry & Biochemistry , University of Delaware , Newark , Delaware 19716 , United States.ORCID 0000-0002-8351-8731
Corey H BaschDepartment of Chemistry & Biochemistry , University of Delaware , Newark , Delaware 19716 , United States.
Megan E HoerrnerDepartment of Chemistry & Biochemistry , University of Delaware , Newark , Delaware 19716 , United States.
Michael R TalleyDepartment of Chemistry & Biochemistry , University of Delaware , Newark , Delaware 19716 , United States.
Brian P BoscoeMedicine Design, Pfizer Worldwide Research and Development , Groton , Connecticut 06340 , United States.
Joseph W TuckerMedicine Design, Pfizer Worldwide Research and Development , Groton , Connecticut 06340 , United States.
Michelle R GarnseyMedicine Design, Pfizer Worldwide Research and Development , Groton , Connecticut 06340 , United States.
Mary P WatsonDepartment of Chemistry & Biochemistry , University of Delaware , Newark , Delaware 19716 , United States.ORCID 0000-0002-1879-5257

Funding

This renovation project will create over 1455 sq. ft. of state- of-the-art reseaP20GM104316 · NIGMS · UNIVERSITY OF DELAWARE · PI SCHMITZ, KARL ROBERT · 2014 to 2024
$26.8M
Molecular Design of Advanced BiomaterialsP20GM103541 · NIGMS · UNIVERSITY OF DELAWARE · PI POLENOVA, TATYANA · 2012 to 2012
$2.1M
Cross Couplings of Amine and Alcohol Derivatives to Give Enantioenriched ProductsR01GM111820 · NIGMS · UNIVERSITY OF DELAWARE · PI WATSON, MARY P · 2014 to 2018
$1.6M
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 R01 GM111820NIH HHS S10 OD016267
6 · The paper itself

Abstract

A nickel-catalyzed reductive cross-coupling of alkylpyridinium salts and aryl bromides has been developed using Mn as the reductant. Both primary and secondary alkylpyridinium salts can be used, and high functional group and heterocycle tolerance is observed, including for protic groups. Mechanistic studies indicate the formation of an alkyl radical, and controlling its fate was key to the success of this reaction.

Indexed as

BromineAminesBoronic AcidsCatalysisFree RadicalsMagnesium ChlorideManganeseNickelOxidation-ReductionPyridinesPyridinium CompoundsAminesBoronic AcidsBromineFree RadicalsMagnesium ChlorideManganeseNickelnickel chloridePyridinesPyridinium Compounds

Identifiers

PMID30917282
PMCPMC6517243

What OpenQuestion holds

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Read underepoch 390

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.