887144-97-0Relevant articles and documents
Supramolecular Aggregation of Perfluoroorganyl Iodane Reagents in the Solid State and in Solution
Liebing, Phil,Pietrasiak, Ewa,Otth, Elisabeth,Kalim, Jorna,Bornemann, Dustin,Togni, Antonio
, p. 3771 - 3781 (2018/07/31)
The crystal structures of different perfluoroorganyl iodanes are described, including those of four new benziodoxole derivatives with RF = n-C3F7, n-C4F9, n-C8F17, and C6F5. In all of the compounds, the iodine atom shows significant Lewis acidity, and the fourth coordination site is readily filled by secondary bonding interactions to produce square-planar coordination. Although this geometry is a good model for benziodoxoles, benziodoxolone derivatives tend to aggregate further through additional weak I···O or I···aryl contacts. The different interactions lead to the formation of various assemblies with different dimensions in the solid state. The protonation of the reagents results in the formation of entirely different supramolecular structures, which are supported by hydrogen bonding. The structural features of the reagents in the solid state reflect well their behavior in solution, and the I–C(RF) bond is influenced by the coordination of Lewis basic solvents to the iodine atom and by hydrogen bonding with protic solvents. These solvent effects are more pronounced for reagents containing the trifluoromethyl fragment than for derivatives with longer RF chains.
Recyclable Trifluoromethylation Reagents from Fluoroform
Geri, Jacob B.,Szymczak, Nathaniel K.
supporting information, p. 9811 - 9814 (2017/08/03)
We present a strategy to rationally prepare CF3- transfer reagents at ambient temperature from HCF3. We demonstrate that a highly reactive CF3- adduct can be synthesized from alkali metal hydride, HCF3, and borazine Lewis acids in quantitative yield at room temperature. These nucleophilic reagents transfer CF3- to substrates without additional chemical activation, and after CF3 transfer, the free borazine is quantitatively regenerated. These features enable syntheses of popular nucleophilic, radical, and electrophilic trifluoromethylation reagents with complete recycling of the borazine Lewis acid.
One-pot synthesis of hypervalent iodine reagents for electrophilic trifluoromethylation
Matousek, Vaclav,Pietrasiak, Ewa,Schwenk, Rino,Togni, Antonio
, p. 6763 - 6768 (2013/07/26)
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.