Evidence map›Paper›PMID 31464131›Full record

ArticleOrganic letters2019

Deaminative Arylation of Amino Acid-derived Pyridinium Salts.

Megan E Hoerrner, Kristen M Baker, Corey H Basch, Earl M Bampo, Mary P Watson

Open access · greenAbstract 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 26 papers.

0numbers the graph read from it
0cells of the map it votes in
26citing papers in PubMed
5.7field-weighted citation impact, top 3% of its field
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

26 citing papers in PubMed, 84 citations in OpenAlex.

  1. Article
  2. Deaminative C(Journal of the American Chemical Society · 2026
    Article
  3. Article
  4. Direct Editing of Cysteine to Electrophilic Alkyl Halides in Peptides.Journal of the American Chemical Society · 2025
    Article
  5. Article
  6. Article
  7. Article
  8. Article
  9. Late-Stage Isotopic Exchange of Primary Amines.Journal of the American Chemical Society · 2023
    Article
  10. Article
  11. Formal Cross-Coupling of Amines and Carboxylic Acids to Form spJournal of the American Chemical Society · 2023
    Article
  12. Article
  13. Article
  14. Article
  15. Traceless Benzylic C-H Amination via Bifunctional N-Aminopyridinium Intermediates.Angewandte Chemie (International ed. in English) · 2022
    Article
  16. Article
  17. Review
  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

5 authors at 1 institution in 1 country.

Megan E HoerrnerDepartment of Chemistry & Biochemistry , University of Delaware , Newark , Delaware 19716 , United States.
Kristen M BakerDepartment of Chemistry & Biochemistry , University of Delaware , Newark , Delaware 19716 , United States.
Corey H BaschDepartment of Chemistry & Biochemistry , University of Delaware , Newark , Delaware 19716 , United States.
Earl M BampoDepartment of Chemistry & Biochemistry , University of Delaware , Newark , Delaware 19716 , United States.
Mary P WatsonDepartment of Chemistry & Biochemistry , University of Delaware , Newark , Delaware 19716 , United States.ORCID 0000-0002-1879-5257
University of Delaware · US

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
Supplement to Harnessing Alkyl Amines and Alkyl Alcohols in Cross-CouplingR35GM131816 · NIGMS · UNIVERSITY OF DELAWARE · PI Mary P Watson · 2019 to 2026
$3.4M
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 GM111820NIGMS NIH HHS R35 GM131816NIH HHS S10 OD016267
6 · The paper itself

Abstract

A Suzuki-Miyaura cross-coupling of α-pyridinium esters and arylboroxines has been developed. Combined with formation of the pyridinium salts from amino acid derivatives, this method enables amino acid derivatives to be efficiently transformed into α-aryl esters and amides. Under the mild conditions, broad functional group tolerance on both the amino acid derivatives and the arylboroxine are observed, including protic functional groups. Mechanistic studies support an alkyl radical intermediate, similar to other cross-couplings of alkylpyridinium salts.

Indexed as

AmidesAmino AcidsBoron CompoundsDeaminationEstersMolecular StructurePyridinesSaltsAmidesAmino AcidsBoron CompoundsEstersPyridinesSalts

Identifiers

PMID31464131
PMCPMC6894616
OpenAlexW2970304856

What OpenQuestion holds

Textmetadata
LicenceTDM
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.