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Updated: Dec 21, 2025

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
Published on: September 8, 2013
Electrophilic Cyanative Alkenylation of Arenes
Mingyue Zhao1, Alejandro G Barrado1, Kristin Sprenger1
1Institut für Organische und Biomolekulare Chemie, Georg August Universität Göttingen, Tammannstr 2, 37077 Göttingen, Germany.
Abstract:
A variety of appropriately substituted internal alkynes were transformed into the corresponding cyano-substituted phenanthrenes, dihydronaphthalenes, and cyclohepta-1,3,5-trienes in moderate to excellent yields by treatment with imidazolium thiocyanate 1, which serves as an easy to handle [CN]+ precursor, in the presence of BCl3. The synthetic value of the method is additionally demonstrated by the transformation of the primarily obtained products into heavily substituted quinolines. Additionally, the dynamic properties of the prepared dibenzocyclohepta-1,3,5-trienes have been investigated.
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