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 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.