4.7 Article

One-Pot Synthesis of Hypervalent Iodine Reagents for Electrophilic Trifluoromethylation

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 78, Issue 13, Pages 6763-6768

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jo400774u

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Funding

  1. ETH Zurich

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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 In both cases, the stoichiometric oxidants sodium metaperiodate and tertbutyl hypochlorite have been replaced by trichloroisocyanuric acid.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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