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Updated: May 10, 2026

Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes
Published on: September 12, 2018
One-pot synthesis of hypervalent iodine reagents for electrophilic trifluoromethylation
Václav Matoušek1, Ewa Pietrasiak, Rino Schwenk
1Department of Chemistry and Applied Biosciences, Swiss Federal Institute of Technology, ETH Zürich, CH-8093 Zürich, Switzerland.
Abstract:
Simplified syntheses suited for large scale preparations of the two hypervalent iodine reagents 1 and 2 for electrophilic trifluoromethylation are reported. In both cases, the stoichiometric oxidants sodium metaperiodate and tert-butyl hypochlorite have been replaced by trichloroisocyanuric acid. Reagent 1 is accessible in a one-pot procedure from 2-iodobenzoic acid in 72% yield. Reagent 2 was prepared via fluoroiodane 11 in a considerably shorter reaction time and with no need of an accurate temperature control.
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