Evidence map›Paper›PMID 36755706›Full record

ArticleChemical science2023

Practical, scalable, and transition metal-free visible light-induced heteroarylation route to substituted oxindoles.

Jadab Majhi, Albert Granados, Bianca Matsuo, Vittorio Ciccone, Roshan K Dhungana, Mohammed Sharique, Gary A Molander

Abstract read
PubMed Full text at PMC Publisher
In one paragraph

Article in Chemical science, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.

0numbers the graph read from it
0cells of the map it votes in
6citing 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

6 citing papers in PubMed.

  1. Article
  2. Article
  3. Review
  4. Review
  5. Recent advances in oxidative radical difunctionalization ofBeilstein journal of organic chemistry · 2025
    Review
  6. Photo-induced carboxylation of C(spNature communications · 2024
    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

7 authors.

Jadab MajhiRoy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania 231 South 34th Street Philadelphia Pennsylvania 19104-6323 USA gmolandr@sas.upenn.edu.ORCID https://orcid.org/0000-0001-8600-304X
Albert GranadosRoy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania 231 South 34th Street Philadelphia Pennsylvania 19104-6323 USA gmolandr@sas.upenn.edu.ORCID https://orcid.org/0000-0002-5362-5966
Bianca MatsuoRoy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania 231 South 34th Street Philadelphia Pennsylvania 19104-6323 USA gmolandr@sas.upenn.edu.
Vittorio CicconeRoy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania 231 South 34th Street Philadelphia Pennsylvania 19104-6323 USA gmolandr@sas.upenn.edu.ORCID https://orcid.org/0000-0002-7329-245X
Roshan K DhunganaRoy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania 231 South 34th Street Philadelphia Pennsylvania 19104-6323 USA gmolandr@sas.upenn.edu.
Mohammed ShariqueRoy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania 231 South 34th Street Philadelphia Pennsylvania 19104-6323 USA gmolandr@sas.upenn.edu.
Gary A MolanderRoy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania 231 South 34th Street Philadelphia Pennsylvania 19104-6323 USA gmolandr@sas.upenn.edu.ORCID https://orcid.org/0000-0002-9114-5584

Funding

Accessing New Chemical Space via Organic SynthesisR35GM131680 · NIGMS · UNIVERSITY OF PENNSYLVANIA · PI MOLANDER, GARY A · 2019 to 2022
$2.4M
Targeting Nucleic Acid Junctions with Small MoleculesR01GM118510 · NIGMS · UNIVERSITY OF PENNSYLVANIA · PI CHENOWETH, DAVID MICHAEL · 2016 to 2020
$1.6M
NIGMS NIH HHS R01 GM118510NIGMS NIH HHS R35 GM131680
6 · The paper itself

Abstract

The synthetic application of (hetero)aryl radicals in organic synthesis has been known since the last century. However, their applicability has significantly suffered from ineffective generation protocols. Herein, we present a visible-light-induced transition metal-free (hetero)aryl radical generation from readily available (hetero)aryl halides for the synthesis of 3,3'-disubstituted oxindoles. This transformation is amenable to a wide range of (hetero)aryl halides as well as several easily accessible acrylamides, and it is also scalable to multigram synthesis. Finally, the versatility of the oxindole products is demonstrated through their conversion to a variety of useful intermediates applicable to target-directed synthesis.

Identifiers

PMID36755706
PMCPMC9890556

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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.