Evidence map›Paper›PMID 35484155›Full record

ArticleNature communications2022

Reactant-induced photoactivation of in situ generated organogold intermediates leading to alkynylated indoles via Csp

Fen Zhao, Mehdi Abdellaoui, Wided Hagui, Maria Ballarin-Marion, Jérôme Berthet, Vincent Corcé, Stéphanie Delbaere, Héloïse Dossmann, Agathe Espagne, Jérémy Forté and 5 more

Open access · goldAbstract read
In one paragraph

Article in Nature communications, 2022. 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
3.2field-weighted citation impact, top 8% 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

6 citing papers in PubMed, 30 citations in OpenAlex.

  1. Photosensitizing Au(I) Catalysis With Coumarins.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026
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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

15 authors at 2 institutions in 2 countries.

Fen Zhao *Sorbonne Université, CNRS, Institut Parisien de Chimie Moléculaire, 4 Place Jussieu, 75005, Paris, France.
Mehdi Abdellaoui *Sorbonne Université, CNRS, Institut Parisien de Chimie Moléculaire, 4 Place Jussieu, 75005, Paris, France.
Wided HaguiSorbonne Université, CNRS, Institut Parisien de Chimie Moléculaire, 4 Place Jussieu, 75005, Paris, France.
Maria Ballarin-MarionSorbonne Université, CNRS, Institut Parisien de Chimie Moléculaire, 4 Place Jussieu, 75005, Paris, France.
Jérôme BerthetUniv Lille, INSERM, CHU Lille, UMR-S 1172, Lille Neuroscience and Cognition Research Center, 59000, Lille, France.ORCID http://orcid.org/0000-0002-9868-3983
Vincent CorcéSorbonne Université, CNRS, Institut Parisien de Chimie Moléculaire, 4 Place Jussieu, 75005, Paris, France.
Stéphanie DelbaereUniv Lille, INSERM, CHU Lille, UMR-S 1172, Lille Neuroscience and Cognition Research Center, 59000, Lille, France.ORCID http://orcid.org/0000-0001-6846-6614
Héloïse DossmannSorbonne Université, CNRS, Institut Parisien de Chimie Moléculaire, 4 Place Jussieu, 75005, Paris, France.ORCID http://orcid.org/0000-0003-4844-229X
Agathe EspagnePASTEUR, Département de Chimie, École Normale Supérieure, PSL University, Sorbonne Université, CNRS, 24, Rue Lhomond, 75005, Paris, France.
Jérémy FortéSorbonne Université, CNRS, Institut Parisien de Chimie Moléculaire, 4 Place Jussieu, 75005, Paris, France.ORCID http://orcid.org/0000-0002-9363-4162
Ludovic JullienPASTEUR, Département de Chimie, École Normale Supérieure, PSL University, Sorbonne Université, CNRS, 24, Rue Lhomond, 75005, Paris, France.
Thomas Le SauxPASTEUR, Département de Chimie, École Normale Supérieure, PSL University, Sorbonne Université, CNRS, 24, Rue Lhomond, 75005, Paris, France.ORCID http://orcid.org/0000-0002-2387-2624
Virginie Mouriès-MansuySorbonne Université, CNRS, Institut Parisien de Chimie Moléculaire, 4 Place Jussieu, 75005, Paris, France. virginie.mansuy@sorbonne-universite.fr.ORCID http://orcid.org/0000-0003-1804-4848
Cyril OllivierSorbonne Université, CNRS, Institut Parisien de Chimie Moléculaire, 4 Place Jussieu, 75005, Paris, France. cyril.ollivier@sorbonne-universite.fr.ORCID http://orcid.org/0000-0003-2416-4467
Louis FensterbankSorbonne Université, CNRS, Institut Parisien de Chimie Moléculaire, 4 Place Jussieu, 75005, Paris, France. louis.fensterbank@sorbonne-universite.fr.ORCID http://orcid.org/0000-0003-0001-7120
Centre National de la Recherche Scientifique · FRInserm · FR

Funding

Agence Nationale de la Recherche (French National Research Agency) ANR-17- CE07-001Agence Nationale de la Recherche (French National Research Agency) ANR-20-CE07-0038
6 · The paper itself

Abstract

Photosensitization of organogold intermediates is an emerging field in catalysis. In this context, an access to 2,3-disubstituted indoles from o-alkynyl aniline and iodoalkyne derivatives via a gold-catalyzed sequence under visible-light irradiation and in the absence of an exogenous photocatalyst was uncovered. A wide scope of the process is observed. Of note, 2-iodo-ynamides can be used as electrophiles in this cross-coupling reaction. The resulting N-alkynyl indoles lend themselves to post-functionalization affording valuable scaffolds, notably benzo[a]carbazoles. Mechanistic studies converge on the fact that a potassium sulfonyl amide generates emissive aggregates in the reaction medium. Static quenching of these aggregates by a vinylgold(I) intermediate yields to an excited state of the latter, which can react with an electrophile via oxidative addition and reductive elimination to forge the key C-C bond. This reactant-induced photoactivation of an organogold intermediate opens rich perspectives in the field of cross-coupling reactions.

Identifiers

PMID35484155
PMCPMC9051093
OpenAlexW4225163453

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.