Evidence map›Paper›PMID 34403571›Full record

ArticleAngewandte Chemie (International ed. in English)2021

Direct Photoexcitation of Ethynylbenziodoxolones: An Alternative to Photocatalysis for Alkynylation Reactions*.

Stephanie G E Amos, Diana Cavalli, Franck Le Vaillant, Jerome Waser

Open access · hybridAbstract read
In one paragraph

Article in Angewandte Chemie (International ed. in English), 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 16 papers.

0numbers the graph read from it
0cells of the map it votes in
16citing papers in PubMed
3.9field-weighted citation impact, top 5% 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

16 citing papers in PubMed, 47 citations in OpenAlex.

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  10. Recent progress in alkynylation with hypervalent iodine reagents.Chemical communications (Cambridge, England) · 2023
    Review
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  12. Article
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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 at 2 institutions in 2 countries.

Stephanie G E AmosLaboratory of Catalysis and Organic Synthesis and National Centre of Competence in Research (NCCR) Catalysis, Institut des Sciences et Ingénierie Chimique, Ecole Polytechnique Fédérale de Lausanne, CH-1015, Lausanne, Switzerland.ORCID http://orcid.org/0000-0002-8718-1048
Diana CavalliLaboratory of Catalysis and Organic Synthesis and National Centre of Competence in Research (NCCR) Catalysis, Institut des Sciences et Ingénierie Chimique, Ecole Polytechnique Fédérale de Lausanne, CH-1015, Lausanne, Switzerland.ORCID http://orcid.org/0000-0002-6675-760X
Franck Le VaillantMax-Planck-Institut für Kohlenforschung, Mülheim an der Ruhr, 45470, Germany.ORCID http://orcid.org/0000-0002-2723-1787
Jerome WaserLaboratory of Catalysis and Organic Synthesis and National Centre of Competence in Research (NCCR) Catalysis, Institut des Sciences et Ingénierie Chimique, Ecole Polytechnique Fédérale de Lausanne, CH-1015, Lausanne, Switzerland.ORCID http://orcid.org/0000-0002-4570-914X
École Polytechnique Fédérale de Lausanne · CHMax-Planck-Institut für Kohlenforschung · DE

Funding

fp7 ideas: european research council ERC Starting Grant 334840schweizerischer nationalfonds zur förderung der wissenschaftlichen forschung NCCR Catalysis
6 · The paper itself

Abstract

Ethynylbenziodoxolones (EBXs) are commonly used as radical traps in photocatalytic alkynylations. Herein, we report that aryl-substituted EBX reagents can be directly activated by visible light irradiation. They act as both oxidants and radical traps, alleviating the need for a photocatalyst in several reported EBX-mediated processes, including decarboxylative and deboronative alkynylations, the oxyalkynylation of enamides and the C-H alkynylation of THF. Furthermore, the method could be applied to the synthesis of alkynylated quaternary centers from tertiary alcohols via stable oxalate salts and from tertiary amines via aryl imines. A photocatalytic process using 4CzIPN as an organic dye was also developed for the deoxyalkynylation of oxalates.

Indexed as

alkyneshypervalent iodinephotochemistryquaternary centerssynthetic methods

Identifiers

PMID34403571
PMCPMC8596672
OpenAlexW3195772990

What OpenQuestion holds

Textmetadata
LicenceCC BY
Read underepoch 390

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.