| Autor: |
Vincent Corcé, Jérôme Berthet, Mehdi Abdellaoui, Héloïse Dossmann, Louis Fensterbank, Fen Zhao, Cyril Ollivier, Virginie Mouriès-Mansuy, Stéphanie Delbaere, Thomas Le Saux, Jérémy Forté, Ludovic Jullein, Agathe Espagne |
| Rok vydání: |
2021 |
| Předmět: |
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| Popis: |
A novel 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 was observed. Of note, 2-iodo-ynamides that have never been used in any organometallic cross-coupling reaction could be used as electrophiles. The resulting N-alkynyl indoles lend themselves to post-functionalization affording valuable scaffolds, notably benzo[a]carbazoles. Mechanistic studies converged 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. |
| Databáze: |
OpenAIRE |
| Externí odkaz: |
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