Evidence map›Paper›PMID 29461537›Full record

ArticleNature chemistry2018

Palladium-catalysed anti-Markovnikov selective oxidative amination.

Daniel G Kohler, Samuel N Gockel, Jennifer L Kennemur, Peter J Waller, Kami L Hull

Abstract read
In one paragraph

Article in Nature chemistry, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 21 papers.

0numbers the graph read from it
0cells of the map it votes in
21citing 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

21 citing papers in PubMed.

  1. Article
  2. Article
  3. Pd- and Cu-Cocatalyzed Anaerobic Olefin Aminoboration.The Journal of organic chemistry · 2025
    Article
  4. Article
  5. Article
  6. Article
  7. Palladium and Iron Cocatalyzed Aerobic Alkene Aminoboration.Journal of the American Chemical Society · 2023
    Article
  8. Article
  9. Article
  10. Article
  11. Article
  12. Article
  13. γ-Selective C(spNature communications · 2021
    Article
  14. Article
  15. Article
  16. Article
  17. Article
  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.

Daniel G KohlerDepartment of Chemistry, University of Illinois, Urbana-Champaign, 600 S. Mathews, Urbana, Illinois 61801, USA.
Samuel N GockelDepartment of Chemistry, University of Illinois, Urbana-Champaign, 600 S. Mathews, Urbana, Illinois 61801, USA.
Jennifer L KennemurDepartment of Chemistry, University of Illinois, Urbana-Champaign, 600 S. Mathews, Urbana, Illinois 61801, USA.
Peter J WallerDepartment of Chemistry, University of Illinois, Urbana-Champaign, 600 S. Mathews, Urbana, Illinois 61801, USA.
Kami L HullDepartment of Chemistry, University of Illinois, Urbana-Champaign, 600 S. Mathews, Urbana, Illinois 61801, USA.ORCID 0000-0003-3102-2686

Funding

Transition Metal-Catalyzed Alkene FunctionalizationR35GM125029 · NIGMS · UNIVERSITY OF TEXAS AT AUSTIN · PI Kami Lee Hull · 2017 to 2026
$2.7M
NIGMS NIH HHS R35 GM125029
6 · The paper itself

Abstract

In recent years, the synthesis of amines and other nitrogen-containing motifs has been a major area of research in organic chemistry because they are widely represented in biologically active molecules. Current strategies rely on a multistep approach and require one reactant to be activated prior to the carbon-nitrogen bond formation. This leads to a reaction inefficiency and functional group intolerance. As such, a general approach to the synthesis of nitrogen-containing compounds from readily available and benign starting materials is highly desirable. Here we present a palladium-catalysed oxidative amination reaction in which the addition of the nitrogen occurs at the less-substituted carbon of a double bond, in what is known as anti-Markovnikov selectivity. Alkenes are shown to react with imides in the presence of a palladate catalyst to generate the terminal imide through trans-aminopalladation. Subsequently, olefin isomerization occurs to afford the thermodynamically favoured products. Both the scope of the transformation and mechanistic investigations are reported.

Indexed as

AminationAminesCatalysisMolecular StructureOxidation-ReductionPalladiumAminesPalladium

Identifiers

PMID29461537
PMCPMC6092016

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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.