Azide-alkyne cycloadditions with an electronically activated alkyne: indole formation via 1-aryl-1,2,3-triazole-derived imino carbenes

Azide-alkyne cycloadditions with an electronically activated alkyne: indole formation via 1-aryl-1,2,3-triazole-derived imino carbenes

We report that the use of a diaminoalkyne in the azide-alkyne cycloaddition with aryl azides leads to 3 -indoles under mild, uncatalysed conditions. Computations reveal that N extrusion from, in one case, isolable triazoles is facile, generating imino carbenes, which undergo intramolecular aryl C-H...

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Veröffentlicht in:Chemical communications (Cambridge, England) England), 2022-02, Vol.58 (14), p.2331-2334
Hauptverfasser: Kachel, Stephanie, Jayaraman, Arumugam, Okorn, Alexander, Krummenacher, Ivo, Drescher, Regina, Brunecker, Carina, Fuchs, Sonja, Heß, Merlin, Stennett, Tom E, Braunschweig, Holger
Format: Artikel
Sprache:eng
Schlagworte:
Alkynes
Aromatic compounds
Carbenes
Cycloaddition
Extrusion
Hydrogen bonds
Indoles
Triazoles
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Beschreibung
Zusammenfassung:We report that the use of a diaminoalkyne in the azide-alkyne cycloaddition with aryl azides leads to 3 -indoles under mild, uncatalysed conditions. Computations reveal that N extrusion from, in one case, isolable triazoles is facile, generating imino carbenes, which undergo intramolecular aryl C-H bond activation and give 3 -indoles as products.
ISSN:1359-7345
1364-548X
DOI:10.1039/d1cc06975f