Schnürch Lab
Current research:
Direct functionalization of C(sp3)-H bonds:
The direct functionalization of C-H bonds is a hot and rapidly growing field in organic synthesis. Exploiting the C-H bond as “functional group” opens the door for more efficient and sustainable processes. Within this field, the activation of C(sp3)-H bonds is a particular challenge. In the past years we have developed several reactions under ruthenium, rhodium, copper, and iron catalysis realizing arylation, indolation, and alkylation reactions. Recently, our focus has shifted to the field of coupling two different C(sp3)-H bonds with each other, an even greater challenge.
Solid substitutes for gaseous reagents:
The aim of this project is to incorporate small alkyl chains into more complex organic molecules using easy to handle reagents. The type of reagents preferred in organic synthesis is solid, non-toxic, non-corrosive, and stable for a prolonged period of time without special precautions. Unfortunately, the reagents currently in use for the introduction of short alkyl chains do not fulfill these criteria in many cases, since they are often gaseous, toxic, or corrosive or even a combination of the aforementioned undesirable properties. So, what to do, in case you want to use such reagents, but change their properties to make handling easier?
The hypothesis is that new reagents can be developed, which are solid and easy to handle themselves, but deliver in-situ the actual alkylation reagent, overall without experiencing the aforementioned unfavorable properties. For that purpose, we will look into several reagent classes, which can decompose under certain reaction conditions into reactive intermediates, which in turn can act as alkylating agents. Additionally, it has to be secured that the conditions required for liberating the alkylation reagent in-situ, are compatible with the other substrates, catalysts, and overall reaction conditions. The method development will start with selected test substrates and transformations, before the general scope of a certain method will be explored.
Organic small molecules for energy storage:
This research was initiated in the frame of a FFG “Leitprojekt” named Tes4seT – Thermal Energy Storage for Sustainable Energy Technology. In this project we were part of a large consortium of 18 partners and 5 development lines. The overall goal was to develop advanced thermal storage materials, thermal storage devices, numerical simulation tools and control systems to integrate these into energy systems in industry, for mobility applications and in buildings, in order to strengthen these sectors and bring the Austrian industry in a leading European position regarding advanced thermal energy storage. In our project part we cooperated with the Austrian Institute of Technology (AIT), the Austrian company SOLID and the German company Südzucker AG. Our aim was to use derivatives of sugar alcohols to store energy via a phase transfer from the solid to the liquid phase and release it afterwards by inducing crystallization. It turned out that such sugar alcohols are not stable for the desired application, however at the end of the project we identified two new compound classes which have the desired properties.
Ligands for GABAA Receptors:
This project is carried out in collaboration with Assoc. Prof. Margot Ernst from the Medical University of Vienna In the Ernst group biological testing is carried out and my group is charged with the chemical synthesis and lead optimization. The aim of the present project is the development and characterization of compound libraries that target a binding site of a GABAA receptors (gamma-amino butyric acid type A receptors) with a distinct subunit composition. GABAA receptors are the site of action of many clinically important drugs, such as benzodiazepines or barbiturates and the targets for sleep medications, anxiolytics, or various narcotics. In this collaborative effort we generate and investigate new compounds that interact with this site, try to understand the interactions that govern the ligated states and lead to allosteric modulation, and ultimately produce compounds exhibiting higher potency and selectivity for these binding sites for a possible future therapeutic application. Isotopic labelling for developing probe molecules is one of the next research plans on the agenda.
Michael Schnürch has carried out his diploma and PhD thesis in the group of Prof. Peter Stanetty and received his PhD in 2005 from TU Wien. During his PhD-studies, he was on a 4-month sabbatical in Canada where he worked in the group of Prof. Victor Snieckus at Queens University (Kingston, Ontario). He was then Post-Doc with Prof. Dalibor Sames at the Columbia University in New York City (as Erwin Schrödinger fellow) and conducted research in the field of decarbonylative coupling reactions and sp3 C-H activation. After his return, he became Assistant Professor at TU Wien and completed his habilitation in 2013. He was promoted to privatdozent and in 2016 to Associate Professor for Organometallic Chemistry, a position he still holds. His research interests are located in the field of synthesis of heterocyclic compounds for the manipulation of cell differentiation and GABAA receptors, C-H activation of sp3 centers, the substitution of gaseous reagents for solid alternatives, green chemistry, and mechanochemistry.
GreenChem TechHub
SUGARS
Substituting Gaseous Reagents for Solid Alternatives (SUGARS) – FWF Project P33064N
The aim of this project is to incorporate small alkyl chains into more complex organic molecules using easy to handle reagents.
The type of reagents preferred in organic synthesis is solid, non-toxic, non-corrosive, and stable for a prolonged period of time without special precautions. Unfortunately, the reagents currently in use for the introduction of short alkyl chains do not fulfill these criteria in many cases, since they are often gaseous, toxic, or corrosive or even a combination of the aforementioned undesirable properties. So, what to do, in case you want to use such reagents, but change their properties to make handling easier?
The hypothesis is that new reagents can be developed, which are solid and easy to handle themselves, but deliver in-situ the actual alkylation reagent, overall without experiencing the aforementioned unfavorable properties.
For that purpose, we will look into several reagent classes, which can decompose under certain reaction conditions into reactive intermediates, which in turn can act as alkylating agents. Additionally, it has to be secured that the conditions required for liberating the alkylation reagent in-situ, are compatible with the other substrates, catalysts, and overall reaction conditions. The method development will start with selected test substrates and transformations, before the general scope of a certain method will be explored.
Realizing this project will expand the scope of transformations which can be carried out under “normal” laboratory conditions without the need for special equipment (e.g. high-pressure reactors often required when working with gaseous reagents). Additionally, transformations with gaseous reagents are often actively avoided in university settings, where the reaction scale is typically in the mg region, and dosing gases in such small amounts is extremely difficult. Hence, this project will potentially open a new chemical space to be exploited in the future by chemists at all different types of institutions.
Finally, the utility of the developed methods shall be demonstrated by the late-stage modification of known drug molecules.
CHAIR
Marie Curie International Training Network – “C-H Activation for Industrial Renewal” – CHAIR
Relying on the functionalisation of previously considered latent, yet omnipresent C-H bonds, C-H activation offers a real breakthrough in organic chemistry and allows reconsidering beaten tracks in synthesis, retrosynthesis and late stage diversification for rapid hit-to-lead strategies.
It is consequently one of the most rapidly expanding fields of synthetic chemistry.
Yet, its implementation in the non-academic sector is still scarce, as numerous obstacles still need to be overcome to render C-H activations truly appealing for a large-scale production of drugs, materials or key building blocks. In addition, current academia-industry interactions are still limited and young researchers able to implement these new competences are rare.
Accordingly, the target and ambition of the CHAIR project is dual: to educate a new generation of young chemists in this modern and promising field of chemistry while concomitantly designing new solutions to further improve the attractiveness of C-H activation for industrial purposes.CHAIR fosters research training of early stage researchers (ESRs, i.e. PhD students) on CH-activation. Our project focuses on establishing strong bridges between academia and industry to develop new C-H activation methodologies and generalise their implementation in industry, from both R&D and production perspectives.
To do so, we are training 15 ESRs within the network’s laboratories, to carry-out 15 research projects.
GABAA Receptor Ligands
GABAA Receptor Ligands
This project is carried out in collaboration with Assoc. Prof. Margot Ernst from the Medical University of Vienna In the Ernst group biological testing is carried out and my group is charged with the chemical synthesis and lead optimization. The aim of the present project is the development and characterization of compound libraries that target a binding site of a GABAA receptors (gamma-amino butyric acid type A receptors) with a distinct subunit composition. GABAA receptors are the site of action of many clinically important drugs, such as benzodiazepines or barbiturates and the targets for sleep medications, anxiolytics, or various narcotics. In this collaborative effort we generate and investigate new compounds that interact with this site, try to understand the interactions that govern the ligated states and lead to allosteric modulation, and ultimately produce compounds exhibiting higher potency and selectivity for these binding sites for a possible future therapeutic application. Isotopic labelling for developing probe molecules is one of the next research plans on the agenda.
Michael Schnürch
Univ.Prof. Dipl.-Ing. Dr.techn.
Connect
- +43 (1) 58801 163616
- michael.schnuerch@tuwien.ac.at
0000-0003-2946-9294