Schoenebeck Research Group
Organogermanes.
In the realm of potential coupling partners, historically, organogermanes have had very low reactivity in cross coupling reactions and remained unnoticed by the scientific community. Our group developed catalytic strategies that for the first time make the organogermanes the most reactive coupling partner in competition with traditionally more established coupling partners, such as boronic acids/esters, halides or silanes.
Selected publications.
Recent Developments with Organogermanes: their Preparation and Application in Synthesis and Catalysis
T. Rogova, E. Ahrweiler, M. D. Schoetz, F. Schoenebeck, Angew. Chem. Int. Ed. 2023, e202314709.
Organogermanes as Orthogonal Coupling Partners in Synthesis and Catalysis
Unlocking uncharted
chemical space.
With function being closely connected to structure (and key functional groups), our objective is to provide access to new chemical space with the development of efficient synthetic methodology. In this context, the group recently provided numerous strategies to unlock access to NCF₃ (and NCF₂H) carbonyl compounds and numerous derivatives.
Selected publications.
Access to N-Difluoromethyl Amides, (Thio)Carbamates, Ureas, and Formamides
F. G. Zivkovic, G. Wycich, L. Liu, F. Schoenebeck, J. Am. Chem. Soc. 2024, 146, 1276.
Access to N-CF₃ Formamides by Reduction of N-CF₃ Carbamoyl Fluorides
F. G. Zivkovic, C. D. T. Nielsen, F. Schoenebeck, Angew. Chem. Int. Ed. 2022, 61, e202213829.
Access to Cyclic N-Trifluoromethyl Ureas through Photocatalytic Activation of Carbamoyl Azides
Straightforward access to N-trifluoromethyl amides, carbamates, thiocarbamates and ureas
T. Scattolin, S. Bouayad-Gervais, F. Schoenebeck, Nature 2019, 573, 102.
Multinuclear metal catalysis
and speciation.
We investigate multinuclear metal catalysts – with an emphasis on Pd and Ni in oxidation state one – for fundamental reactivity questions and to overcome pertinent challenges in organic synthesis.
Selected publications.
Machine Learning-Guided Development of Trialkylphosphine Ni(I) Dimers and Applications in Site-Selective Catalysis
Accelerated dinuclear palladium catalyst identification through unsupervised machine learning
Catalysis with Palladium(I) Dimers
C. Fricke, T. Sperger, M. Mendel, F. Schoenebeck, Angew. Chem. Int. Ed. 2021, 60, 3355.
Selectivity & Diversity.
To accelerate the identification of new function, rapid access to molecules is needed. To this end our group has developed novel strategies for the modular, selective and orthogonal diversification of multi-handle building blocks for the diversification in sp² and sp³ space.
Selected publications.
Triply Selective & Sequential Diversification at C(sp³): Expansion of Alkyl Germane Reactivity for C-C & C-Heteroatom Bond Formation
Modular Generation of (Iodinated) Polyarenes Using Triethylgermane as Orthogonal Masking Group
Catalysis with Palladium(I) Dimers
C. Fricke, T. Sperger, M. Mendel, F. Schoenebeck, Angew. Chem. Int. Ed. 2021, 60, 3355.
Mechanistic Studies &
Physical Organic Chemistry.
We have a strong interest in uncovering the origins of chemical phenomena with a particular passion on exploring fundamentally new reactivity principles, and subsequently applying these in organic synthesis. To this end, we complement experimental studies with state-of-the-art computational chemistry tools ranging from quantum mechanical studies to dynamics.
Selected publications.
Post-Transition-State Dynamic Effects in the Transmetalation of Pd(II)-F to Pd(II)-CF₃
M. Pu, C. D. T. Nielsen, E. Senol, T. Sperger, F. Schoenebeck, JACS Au 2024, 4, 263.
Base-Free Cross-Couplings of Aryl Diazonium Salts in Methanol: Pd(II)-Alkoxy as Reactivity-Controlling Intermediate
Divergent Reactivity of Stannane and Silane in the Trifluoromethylation of Pd(II): Cyclic Transition State versus Difluorocarbene Release
M. Pu, I. A. Sanhueza, E. Senol, F. Schoenebeck, Angew. Chem. Int. Ed. 2018, 57, 15081.
Enabling tools &
Machine Learning.
We incorporate various technologies to overcome mechanistic or synthetic challenges and advance chemistry. These include the application of artificial intelligence, e.g. for the accelerated development of catalysts, but also numerous other technologies, such as flow chemistry, electrochemistry and photochemistry.
Selected publications.
Machine Learning-Guided Development of Trialkylphosphine Ni(I) Dimers and Applications in Site-Selective Catalysis
Access to Cyclic N-Trifluoromethyl Ureas through Photocatalytic Activation of Carbamoyl Azides
Accelerated dinuclear palladium catalyst identification through unsupervised machine learning