Reactant-induced photoactivation of in situ generated organogold intermediates leading to alkynylated indoles via Csp2-Csp cross-coupling

Fen Zhao, Mehdi Abdellaoui, Wided Hagui, Maria Ballarin-Marion, Jérôme Berthet, Vincent Corcé, Stéphanie Delbaere, Héloïse Dossmann, Agathe Espagne, Jérémy Forté, Ludovic Jullien, Thomas Saux, Virginie Mouriès-Mansuy (), Cyril Ollivier () and Louis Fensterbank ()
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Fen Zhao: Sorbonne Université, CNRS, Institut Parisien de Chimie Moléculaire
Mehdi Abdellaoui: Sorbonne Université, CNRS, Institut Parisien de Chimie Moléculaire
Wided Hagui: Sorbonne Université, CNRS, Institut Parisien de Chimie Moléculaire
Maria Ballarin-Marion: Sorbonne Université, CNRS, Institut Parisien de Chimie Moléculaire
Jérôme Berthet: Univ Lille, INSERM, CHU Lille, UMR-S 1172, Lille Neuroscience and Cognition Research Center
Vincent Corcé: Sorbonne Université, CNRS, Institut Parisien de Chimie Moléculaire
Stéphanie Delbaere: Univ Lille, INSERM, CHU Lille, UMR-S 1172, Lille Neuroscience and Cognition Research Center
Héloïse Dossmann: Sorbonne Université, CNRS, Institut Parisien de Chimie Moléculaire
Agathe Espagne: PSL University, Sorbonne Université, CNRS
Jérémy Forté: Sorbonne Université, CNRS, Institut Parisien de Chimie Moléculaire
Ludovic Jullien: PSL University, Sorbonne Université, CNRS
Thomas Saux: PSL University, Sorbonne Université, CNRS
Virginie Mouriès-Mansuy: Sorbonne Université, CNRS, Institut Parisien de Chimie Moléculaire
Cyril Ollivier: Sorbonne Université, CNRS, Institut Parisien de Chimie Moléculaire
Louis Fensterbank: Sorbonne Université, CNRS, Institut Parisien de Chimie Moléculaire

Nature Communications, 2022, vol. 13, issue 1, 1-11

Abstract: 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.

Date: 2022
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DOI: 10.1038/s41467-022-29982-2

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