Evidence map›Paper›PMID 34464528›Full record

ArticleJournal of the American Chemical Society2021

Copper-Catalyzed Cross-Coupling of Benzylic C-H Bonds and Azoles with Controlled

Si-Jie Chen, Dung L Golden, Shane W Krska, Shannon S Stahl

Abstract read
In one paragraph

Article in Journal of the American Chemical Society, 2021. 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. Article
  4. Article
  5. Review
  6. Copper-catalyzed C(spNature communications · 2025
    Article
  7. Article
  8. Article
  9. Article
  10. Article
  11. Polar Heterobenzylic C(spJournal of the American Chemical Society · 2023
    Article
  12. Article
  13. Article
  14. Article
  15. Article
  16. Enantioselective Synthesis ofJournal of the American Chemical Society · 2022
    Article
  17. Traceless Benzylic C-H Amination via Bifunctional N-Aminopyridinium Intermediates.Angewandte Chemie (International ed. in English) · 2022
    Article
  18. Article
  19. Article
  20. SuFExableThe Journal of organic chemistry · 2022
    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

4 authors.

Si-Jie ChenDepartment of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, Wisconsin 53706, United States.ORCID 0000-0001-9836-6892
Dung L GoldenDepartment of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, Wisconsin 53706, United States.ORCID 0000-0002-9044-4873
Shane W KrskaHigh-Throughput Experimentation and Lead Discovery Capabilities, Merck & Co., Inc., Kenilworth, New Jersey 07033, United States.ORCID 0000-0001-9757-9036
Shannon S StahlDepartment of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, Wisconsin 53706, United States.ORCID 0000-0002-9000-7665

Funding

Catalytic Redox Reactions for Pharmaceutical SynthesisR35GM134929 · NIGMS · UNIVERSITY OF WISCONSIN-MADISON · PI Shannon S Stahl · 2020 to 2026
$4.3M
QExactive (Orbitrap) mass spectrometerS10OD020022 · OD · UNIVERSITY OF WISCONSIN-MADISON · PI VESTLING, MARTHA M · 2015 to 2015
$483k
NIGMS NIH HHS R35 GM134929NIH HHS S10 OD020022
6 · The paper itself

Abstract

Azoles are important motifs in medicinal chemistry, and elaboration of their structures via direct N-H/C-H coupling could have broad utility in drug discovery. The ambident reactivity of many azoles, however, presents significant selectivity challenges. Here, we report a copper-catalyzed method that achieves site-selective cross-coupling of pyrazoles and other N-H heterocycles with substrates bearing (hetero)benzylic C-H bonds. Excellent

Indexed as

AzolesBenzenesulfonamidesBenzyl CompoundsCatalysisCopperIndansMolecular StructureOxidantsOxidation-ReductionSulfonamidesAzolesBenzenesulfonamidesBenzyl CompoundsCopperIndansN-fluorobenzenesulfonimideOxidantsSulfonamides

Identifiers

PMID34464528
PMCPMC8487258

What OpenQuestion holds

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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.