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

Stephanie Kachel; Arumugam Jayaraman; Alexander Okorn; Ivo Krummenacher; Regina Drescher; Carina Brunecker; Sonja Fuchs; Merlin Heß; Tom E. Stennett; Holger Braunschweig

doi:10.1039/D1CC06975F

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

Stephanie Kachel,‡^ab Arumugam Jayaraman,

‡^ab Alexander Okorn,^ab Ivo Krummenacher,^ab Regina Drescher,^ab Carina Brunecker,^ab Sonja Fuchs,^ab Merlin Heß,^ab Tom E. Stennett^ab and Holger Braunschweig

*^ab

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* Corresponding authors

^a Institute for Inorganic Chemistry, Julius-Maximilians-Universität Würzburg, Am Hubland, Würzburg 97074, Germany
E-mail: h.braunschweig@uni-wuerzburg.de

^b Institute for Sustainable Chemistry & Catalysis with Boron, Julius-Maximilians-Universität Würzburg, Am Hubland, Würzburg 97074, Germany

Abstract

We report that the use of a diaminoalkyne in the azide–alkyne cycloaddition with aryl azides leads to 3H-indoles under mild, uncatalysed conditions. Computations reveal that N₂ extrusion from, in one case, isolable triazoles is facile, generating imino carbenes, which undergo intramolecular aryl C–H bond activation and give 3H-indoles as products.

Chemical Communications

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

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

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