Evidence map›Paper›PMID 37184831›Full record

ArticleJournal of the American Chemical Society2023

Formal Cross-Coupling of Amines and Carboxylic Acids to Form sp

James L Douthwaite, Ruheng Zhao, Eunjae Shim, Babak Mahjour, Paul M Zimmerman, Tim Cernak

Open access · hybridAbstract read
In one paragraph

Article in Journal of the American Chemical Society, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 18 papers.

0numbers the graph read from it
0cells of the map it votes in
18citing papers in PubMed
6.9field-weighted citation impact, top 2% 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

18 citing papers in PubMed, 46 citations in OpenAlex.

  1. Article
  2. Quaternary Carbons from Amines and Acids.Journal of the American Chemical Society · 2026
    Article
  3. Article
  4. Article
  5. Article
  6. Aryl Acid-Alcohol Cross-Coupling: C(spJournal of the American Chemical Society · 2025
    Article
  7. Review
  8. Article
  9. Nickel-Catalyzed Electrochemical Cross-Electrophile C(spAngewandte Chemie (International ed. in English) · 2024
    Article
  10. Article
  11. Article
  12. Ligand Relay for Nickel-Catalyzed Decarbonylative Alkylation of Aroyl Chlorides.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024
    Article
  13. Article
  14. Article
  15. Article
  16. Article
  17. Article
  18. 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

6 authors at 1 institution in 1 country.

James L DouthwaiteDepartment of Medicinal Chemistry, College of Pharmacy, University of Michigan, Ann Arbor, Michigan 48109, United States.ORCID 0000-0002-4478-9010
Ruheng ZhaoDepartment of Medicinal Chemistry, College of Pharmacy, University of Michigan, Ann Arbor, Michigan 48109, United States.
Eunjae ShimDepartment of Chemistry, University of Michigan, Ann Arbor, Michigan 48109, United States.ORCID 0000-0002-4085-9659
Babak MahjourDepartment of Medicinal Chemistry, College of Pharmacy, University of Michigan, Ann Arbor, Michigan 48109, United States.ORCID 0000-0002-8225-6514
Paul M ZimmermanDepartment of Chemistry, University of Michigan, Ann Arbor, Michigan 48109, United States.ORCID 0000-0002-7444-1314
Tim CernakDepartment of Medicinal Chemistry, College of Pharmacy, University of Michigan, Ann Arbor, Michigan 48109, United States.
University of Michigan · US

Funding

Mechanism-Guided Catalyst Development through Reaction Discovery Simulation - Equipment SupplementR35GM128830 · NIGMS · UNIVERSITY OF MICHIGAN AT ANN ARBOR · PI ZIMMERMAN, PAUL · 2018 to 2022
$1.9M
New Amine-Acid Couplings and Their Impact on Medicinal PropertiesR01GM144471 · NIGMS · UNIVERSITY OF MICHIGAN AT ANN ARBOR · PI CERNAK, TIMOTHY · 2022 to 2025
$1.6M
NIGMS NIH HHS R01 GM144471NIGMS NIH HHS R35 GM128830
6 · The paper itself

Abstract

Amines and carboxylic acids are abundant synthetic building blocks that are classically united to form an amide bond. To access new pockets of chemical space, we are interested in the development of amine-acid coupling reactions that complement the amide coupling. In particular, the formation of carbon-carbon bonds by formal deamination and decarboxylation would be an impactful addition to the synthesis toolbox. Here, we report a formal cross-coupling of alkyl amines and aryl carboxylic acids to form C(sp

Identifiers

PMID37184831
PMCPMC10214451
OpenAlexW4376630930

What OpenQuestion holds

Textmetadata
LicenceCC BY-NC-ND
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.