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2 article(s) from Togni, Antonio

Synthesis, characterization and initial evaluation of 5-nitro-1-(trifluoromethyl)-3H-1λ³,2-benziodaoxol-3-one

Nico Santschi,
Roman C. Sarott,
Elisabeth Otth,
Reinhard Kissner and
Antonio Togni

Beilstein J. Org. Chem. 2014, 10, 1–6, doi:10.3762/bjoc.10.1

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Figure 1: Electrophilic trifluoromethylating agents 1 and 2.

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Scheme 1: Synthesis of 5-nitro-1-(trifluoromethyl)-3H-1λ³,2-benziodaoxol-3-one (3).

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Figure 2: UV–vis spectra of reagents 2 (green) and 3 (blue) in DMSO/H₂O 1:1.

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Figure 3: ORTEP representation of X-ray structures 6 and 3. Thermal ellipsoids set to 30% probability. Hydrog...

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Figure 4: DSC traces obtained for 2 (green) and 3 (blue).

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Figure 5: Cyclic voltammetry of 3 (1 mM, black) and of a mixture of 3 (1 mM) and methyl 2-iodo-5-nitrobenzoat...

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Figure 6: Sample kinetic traces for the decomposition of 2 (green) and 3 (blue) to 4 and 5, respectively, upo...

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Published 02 Jan 2014

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Development of the titanium–TADDOLate-catalyzed asymmetric fluorination of β-ketoesters

Lukas Hintermann,
Mauro Perseghini and
Antonio Togni

Beilstein J. Org. Chem. 2011, 7, 1421–1435, doi:10.3762/bjoc.7.166

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Figure 1: Fluorinated substances of biomedical relevance.

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Scheme 1: Enantioselective electrophilic fluorination catalyzed by TADDOLates K1, K2. TADDOL = α,α,α',α'-tetr...

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Scheme 2: Halogenation of β-ketocarbonyl compounds: Importance of enolization and the potential role of a met...

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Figure 2: Model substrates for catalytic fluorinations, with the degree of enolization determined by ¹H NMR m...

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Figure 3: ¹H NMR (250 MHz) spectra of fluorination reaction mixtures diluted with CDCl₃ and filtered. a) Full...

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Scheme 3: Qualitative ordering of catalytic activity of several Lewis acids in the fluorination 1→1-F.

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Scheme 4: Catalysis of the “neutral” fluorination of β-ketoesters with F–TEDA by Lewis acidic titanium comple...

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Figure 4: Structure of the chiral ansa-metallocene [(EBTHI)Ti(OTf)₂].

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Figure 5: Electrophilic fluorinating reagents of the N–F-type. F–TEDA [27]; NFTh = 1-fluoro-4-hydroxy-1,4-diazoni...

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Scheme 5: Synthesis of trifluoromethyl-substituted TADDOL ligands.

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Scheme 6: Correlation experiments for the assignment of absolute configuration to fluorination products 11-F, ...

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Scheme 7: Mechanistic scheme proposed, based on visual and spectroscopic observations. L = solvent, counterio...

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Figure 6: ¹H NMR spectra of a species of the type A, generated in CD₃CN solution from K1 by ionization in the...

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Figure 7: Steric model explaining the face selectivity observed in the titanium–TADDOLate complex catalyzed f...

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Figure 8: Excerpt from the X-ray structure of a catalyst/substrate complex [Ti(1-naphthyl-TADDOLato)(β-ketoen...

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Published 17 Oct 2011

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Synthesis, characterization and initial evaluation of 5-nitro-1-(trifluoromethyl)-3H-1λ3,2-benziodaoxol-3-one

Development of the titanium–TADDOLate-catalyzed asymmetric fluorination of β-ketoesters

Synthesis, characterization and initial evaluation of 5-nitro-1-(trifluoromethyl)-3H-1λ³,2-benziodaoxol-3-one