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Updated: Dec 23, 2025

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
Published on: September 8, 2013
Indium(III) Catalyzed Reactions of Vinyl Azides and Indoles
Atul A More1, Alex M Szpilman1
1Department of Chemical Sciences, Faculty of Natural Science, Ariel University, Ariel 4070000, Israel.
Abstract:
Indium trichloride catalyzes the reaction of vinyl azides with unfunctionalized indoles to give vinyl indoles. This is the first example of displacement of the azide group by a carbon nucleophile while preserving the vinyl function. The protocol employs very mild reaction conditions and offers excellent yields of diverse 3-vinyl indoles. It is amenable to gram scale. Access to a library of 3,3'-bis(indolyl)methanes through condensation of vinyl azides with 2 equiv of an indole is demonstrated.
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