Evidence map›Paper›PMID 32043879›Full record

ArticleJournal of the American Chemical Society2020

Multicomponent Pyrazole Synthesis from Alkynes, Nitriles, and Titanium Imido Complexes via Oxidatively Induced N-N Bond Coupling.

Adam J Pearce, Robin P Harkins, Benjamin R Reiner, Alexander C Wotal, Rachel J Dunscomb, Ian A Tonks

Open access · greenAbstract read
In one paragraph

Article in Journal of the American Chemical Society, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 23 papers.

0numbers the graph read from it
0cells of the map it votes in
23citing papers in PubMed
6.2field-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

23 citing papers in PubMed, 80 citations in OpenAlex.

  1. Article
  2. Dual Excitation and Dual Emission in a 1,4-Diazepine Bearing an Extended π-System.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025
    Article
  3. 1,2-Dihydropyrimidine synthesisChemical communications (Cambridge, England) · 2025
    Article
  4. Article
  5. RSC advances · 2025
    Article
  6. Review
  7. Article
  8. Article
  9. Mechanistic study of pyrazole synthesisDalton transactions (Cambridge, England : 2003) · 2024
    Article
  10. Article
  11. CpOrganometallics · 2023
    Article
  12. Article
  13. Review
  14. α-Diimine synthesisChemical science · 2022
    Article
  15. Selective propargylic C(spChemical science · 2021
    Article
  16. Article
  17. PJournal of the American Chemical Society · 2021
    Article
  18. Article
  19. Review
  20. Hydrazine Formation via Coupling of a Nickel(III)-NHAngewandte Chemie (International ed. in English) · 2021
    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.

Adam J PearceDepartment of Chemistry, University of Minnesota-Twin Cities, 207 Pleasant Street SE, Minneapolis, Minnesota 55455, United States.
Robin P HarkinsDepartment of Chemistry, University of Minnesota-Twin Cities, 207 Pleasant Street SE, Minneapolis, Minnesota 55455, United States.
Benjamin R ReinerDepartment of Chemistry, University of Minnesota-Twin Cities, 207 Pleasant Street SE, Minneapolis, Minnesota 55455, United States.
Alexander C WotalDepartment of Chemistry, University of Minnesota-Twin Cities, 207 Pleasant Street SE, Minneapolis, Minnesota 55455, United States.
Rachel J DunscombDepartment of Chemistry, University of Minnesota-Twin Cities, 207 Pleasant Street SE, Minneapolis, Minnesota 55455, United States.
Ian A TonksDepartment of Chemistry, University of Minnesota-Twin Cities, 207 Pleasant Street SE, Minneapolis, Minnesota 55455, United States.ORCID 0000-0001-8451-8875
University of Minnesota · US

Funding

Ti-Catalyzed Oxidative Amination ReactionsR35GM119457 · NIGMS · UNIVERSITY OF MINNESOTA · PI Ian Albert Tonks · 2016 to 2026
$4.4M
Upgrade of a 500 MHz NMR Spectrometer for Applications in Biomedical ResearchS10OD011952 · OD · UNIVERSITY OF MINNESOTA · PI HOYE, THOMAS R. · 2012 to 2012
$378k
NIGMS NIH HHS R35 GM119457NIH HHS S10 OD011952
6 · The paper itself

Abstract

Pyrazoles are an important class of heterocycles found in a wide range of bioactive compounds and pharmaceuticals. Pyrazole synthesis often requires hydrazine or related reagents where an intact N-N bond is conservatively installed into a pyrazole precursor fragment. Herein, we report the multicomponent oxidative coupling of alkynes, nitriles, and Ti imido complexes for the synthesis of multisubstituted pyrazoles. This modular method avoids potentially hazardous reagents like hydrazine, instead forming the N-N bond in the final step via oxidation-induced coupling on Ti. The mechanism of this transformation has been studied in-depth through stoichiometric reactions of the key diazatitanacyclohexadiene intermediate, which can be accessed via multicomponent coupling of Ti imidos with nitriles and alkynes, ring opening of 2-imino-2

Indexed as

AlkynesCoordination ComplexesCyclizationModels, ChemicalNitrilesOxidation-ReductionPyrazolesTitaniumAlkynesCoordination ComplexesNitrilesPyrazolesTitanium

Identifiers

PMID32043879
PMCPMC7201868
OpenAlexW3006510869

What OpenQuestion holds

Textmetadata
LicenceTDM
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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.