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Updated: Feb 4, 2026

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
Published on: September 8, 2013
TfOH-Promoted Transition-Metal-Free Cascade Trifluoroethylation/Cyclization of Organic Isothiocyanates by
Cheng-Long Zhao1, Qiu-Yan Han1, Cheng-Pan Zhang1,2
1School of Chemistry, Chemical Engineering and Life Science , Wuhan University of Technology , 205 Luoshi Road , Wuhan 430070 , China.
Abstract:
An efficient and transition-metal-free method for the synthesis of the structurally diversified trifluoroethylthiol phenanthridines and 3,4-dihydroisoquinolines is described. Various 2-isothiocyanobiaryls and aryl alkyl isothiocyanates reacted with phenyl(2,2,2-trifluoroethyl)iodonium triflate in CH2Cl2 in the presence of trifluoromethanesulfonic acid at 40 °C to form the corresponding trifluoroethylation/cyclization products in good to quantitative yields. This work represents the first construction of trifluoroethylthiol phenanthridine and isoquinoline derivatives from isothiocyanates in the absence of transition-metal catalysts by a one-pot procedure.
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