• Home
  • ETH Zurich
  • Department of Chemistry and Applied Biosciences
  • Elisabeth Otth
Elisabeth Otth

Elisabeth Otth
ETH Zurich | ETH Zürich · Department of Chemistry and Applied Biosciences

PhD

About

13
Publications
677
Reads
How we measure 'reads'
A 'read' is counted each time someone views a publication summary (such as the title, abstract, and list of authors), clicks on a figure, or views or downloads the full-text. Learn more
177
Citations

Publications

Publications (13)
Article
Full-text available
We report a mild approach to the synthesis of difluoro(aryl)-λ³-iodanes (aryl-IF2 compounds) and tetrafluoro(aryl)-λ⁵-iodanes (aryl-IF4 compounds) using trichloroisocyanuric acid (TCICA) and potassium fluoride (KF). Under these reaction conditions, selective access to either the I(III)- or I(V)-derivatives is predictable based solely on the substit...
Article
Full-text available
The crystal structures of different perfluoroorganyl iodanes are described, including four new benziodoxole derivatives with RF = nC3F7, nC4F7, nC8F17 and C6F5. In all compounds, the iodine atom shows significant Lewis acidity, and the fourth coordination site is readily filled by secondary bonding interactions, giving rise to a square-planar coord...
Article
Introduction of oxygen and nitrogen into organic molecules is one of the fundamental strategies for their functionalization. Traditional approaches rely on the formation of an activated intermediate, which is then modified in a subsequent step. Here we report a simple direct oxidative α-acetoxylation and azidation of α-C−H bonds in Tröger's base an...
Article
Starting from N-trifluoromethyl benzimidazole (1), a series of N-trifluoromethyl benzimidazolium salts 2a-f·HA have been prepared and fully characterized. These were engaged in the formation of [Ir(CO)2(NHC)Cl], [Rh(COD)(NHC)Cl], [Se(NHC)], and [Au(NHC)Cl] derivatives. IR analysis of [Ir(CO)2(NHC)Cl] complexes revealed that the trifluoromethyl subs...
Article
The cover picture shows how a hypervalent-iodine-based electrophilic trifluoromethylating agent [3,3-dimethyl-1-(trifluoromethyl)-3H-1λ3,2-benziodoxole] was edited by formally replacing one of the geminal methyl groups with different alkyl substituents. Subsequently, the resulting library was subjected to kinetic characterization in a model reactio...
Article
We report on the effect of small side-chain modifications to the structure of 3,3-dimethyl-1-(trifluoromethyl)-3H-1λ3,2-benziodaoxole (1b) on its reactivity, as expressed by the initial rate v0 in a model reaction, and show how the latter can be successfully correlated to an easily determined physical parameter p, a 13C NMR chemical shift. The rela...
Article
A new method for the activation of the non-benzylic α-C–H bonds in tertiary diamines has been developed. The protocol relies on an N-bromosuccinimide (NBS)-mediated oxidation of carbon atoms next to the nitrogen atoms in the presence of a catalytic amount of Pd(OAc)2 followed by an intermolecular reaction with oxygen- or nitrogen-centered nucleophi...
Article
This report deals with the rapid functionalization of the 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) scaffold by means of electrophilic trifluoromethylation. Subjecting dye 2 to the disclosed protocol led to the successful isolation of 3-trifluoromethylated derivative 9. Subsequent comparison of structural and electronic properties allowed...
Article
The N2P2 macrocyclic ligands (5S,8S,13E,14aS,18aS,19E)-5,8-diphenyl-5,6,7,8,14a,15,16,17,18,18a-decahydro-tribenzo[b,f,l][1,4,8,11]diazadiphosphacyclotetradecine ((1S,4S,9S,10S)-1a) and (5E,7R,8R,9E,15S,18S)-7,8,15,18-tetraphenyl-7,8, 15,16,17,18-hexahydrodibenzo[f, I] [1,4,8, 11 diazadiphosphacyclotetradecine ((1S,4S,9R,10R)-1b) were prepared by c...
Article
Full-text available
The synthesis of 5-nitro-1-(trifluoromethyl)-3H-1λ(3),2-benziodaoxol-3-one (3), a hypervalent-iodine-based electrophilic trifluoromethylating reagent, is described. Whereas considerations based on cyclic voltammetry and X-ray structural properties would predict an inferior reactivity when compared to the non-nitrated derivative 2, (19)F NMR kinetic...
Article
For the first time, enantioselective catalysis was applied for the preparation of Tröger’s base derivatives affording N-stereogenic building blocks not only in excellent enantiomeric purity but also in an easily scalable fashion. Enzymatic kinetic resolution proved efficient to yield functionalized Tröger’s bases, which can be subsequently modified...
Article
NMR, X-ray, and DFT studies on several [RhCl(diene)(phosphoramidite)] complexes suggest that both electronic and steric effects affect the nature of the olefin, chloride, and P-donor bonding. The X-ray study of [RhCl(1,5-COD)(phosphoramidite)] (phosphoramidite = (Binol)PN(CH(CH3)Ph)2) reveals an intramolecular selectivity in the back-bonding in whi...

Network

Cited By