Antonio Togni - Professor Product Portal

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Professor Antonio Togni

Research in the Togni group focuses on the development of new ligands and reagents. These two general directions thus impact the ability to construct molecules in more efficient or unprecedented ways.

In the field of homogeneous catalysis, our group mainly focuses on the development of new ligands based on ferrocene or N-heterocyclic carbenes. Careful study of such systems allows the understanding of reaction pathways and thus helps in improving the catalytic species. A pertinent example is the Josiphos family of chiral ligands, originally discovered at Ciba-Geigy Ltd. and further developed at Solvias AG, Basel. A ligand of this type is still used in the synthesis of the herbicide (S)-metolachlor which represents the largest industrial-scale application of enantioselective hydrogenation.

In the field of synthetic methodology, we have developed iodine(III) based trifluoromethylation reagents capable of transfering an electrophilic CF3 group to nucleophilic centers including transition metals. These reagents have seen widespread use. This is largely due to their ease of use and the ability to fine-tune reactivity by a variety of activation agents, providing direct access to C-CF3, N-CF3, O-CF3, S-CF3, P-CF3 scaffolds. These emergent fluorinated motifs have spurred further reagent development. For example, we recently reported one of the first electrophilic radical trifluoromethoxy (OCF3) transfer reagent,

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Charpentier J, Früh N, Togni A.
Chem Rev. 2015 Jan 28;115(2):650-82. doi: 10.1021/cr500223h. Epub 2014 Aug 25.
Rosenau CP, Jelier BJ, Gossert AD, Togni A
Angew Chem Int Ed Engl. 2018 Jul 20;57(30):9528-9533. doi: 10.1002/anie.201802620. Epub 2018 May 16.
Fluorine chemistry has taken a pivotal role in chemical reaction discovery, drug development, and chemical biology. NMR spectroscopy, arguably the most important technique for the characterization of fluorinated compounds, is rife with highly inconsistent referencing of fluorine NMR chemical shifts, producing deviations larger tRead More
Jelier BJ, Tripet PF, Pietrasiak E, Franzoni I, Jeschke G, Togni A
Angew Chem Int Ed Engl. 2018 Jun 21. doi: 10.1002/anie.201806296. [Epub ahead of print]
A simple trifluoromethoxylation method enables non-directed functionalization of C-H bonds on a range of substrates, providing access to aryl trifluoromethyl ethers. This light-driven process is distinctly different from conventional procedures and occurs through an OCF3 radical mechanism mediated by a photoredox catalyst, whichRead More