Evidence map›Paper›PMID 36520916›Full record

ArticleScience (New York, N.Y.)2022

Asymmetric intermolecular allylic C-H amination of alkenes with aliphatic amines.

Kelvin Pak Shing Cheung, Jian Fang, Kallol Mukherjee, Andranik Mihranyan, Vladimir Gevorgyan

Abstract read
In one paragraph

Article in Science (New York, N.Y.), 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 40 papers.

0numbers the graph read from it
0cells of the map it votes in
40citing 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

40 citing papers in PubMed.

  1. JACS Au · 2026
    Article
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  8. C(spJournal of the American Chemical Society · 2025
    Article
  9. Article
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  11. Article
  12. Article
  13. Review
  14. Illuminating Palladium Catalysis.Accounts of chemical research · 2025
    Article
  15. Article
  16. Article
  17. Article
  18. Photoinduced Pd-Catalyzed Direct Sulfonylation of Allylic C-H Bonds.Angewandte Chemie (International ed. in English) · 2025
    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.

Kelvin Pak Shing CheungDepartment of Chemistry and Biochemistry, The University of Texas at Dallas, Richardson, TX 75080, USA.ORCID 0000-0002-2433-5556
Jian FangDepartment of Chemistry and Biochemistry, The University of Texas at Dallas, Richardson, TX 75080, USA.ORCID 0000-0002-0604-2987
Kallol MukherjeeDepartment of Chemistry and Biochemistry, The University of Texas at Dallas, Richardson, TX 75080, USA.ORCID 0000-0002-1810-4444
Andranik MihranyanDepartment of Chemistry and Biochemistry, The University of Texas at Dallas, Richardson, TX 75080, USA.ORCID 0000-0001-6801-6496
Vladimir GevorgyanDepartment of Chemistry and Biochemistry, The University of Texas at Dallas, Richardson, TX 75080, USA.ORCID 0000-0002-7836-7596

Funding

Transition Metal-Radical Hybrid Methods for Organic SynthesisR01GM120281 · NIGMS · UNIVERSITY OF TEXAS DALLAS · PI GEVORGYAN, VLADIMIR · 2017 to 2024
$2.5M
NIGMS NIH HHS R01 GM120281
6 · The paper itself

Abstract

Aliphatic allylic amines are found in a great variety of complex and biorelevant molecules. The direct allylic C-H amination of alkenes serves as the most straightforward method toward these motifs. However, use of widely available internal alkenes with aliphatic amines in this transformation remains a synthetic challenge. In particular, palladium catalysis faces the twin challenges of inefficient coordination of Pd(II) to internal alkenes but excessively tight and therefore inhibitory coordination of Pd(II) by basic aliphatic amines. We report a general solution to these problems. The developed protocol, in contrast to a classical Pd(II/0) scenario, operates through a blue light-induced Pd(0/I/II) manifold with mild aryl bromide oxidant. This open-shell approach also enables enantio- and diastereoselective allylic C-H amination.

Identifiers

PMID36520916
PMCPMC10111612

What OpenQuestion holds

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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.