Organic synthesis and transition metal catalysis (Pd, Ru, Cu) is the primary focus of the research group, that includs development of new and improved cataytic reactions, and new synthetic pathways in which transition metal catalysis are involved as an important part of a total synthesis.
We are particularly interested in the synthesis of N-heterocyclic compounds, such as benzo[c]cinnolines, carbazoles, and imidazoles with relevance in medicinal chemistry. The imidazole framework is of particular interest as this motif can be used as precursor for NHC ligands used in organometallics for various catalysts, for example for olefin metathesis, Suzuki cross-coupling, and oxidation catalysts.
Free organic radicals for synthetic applications, development of green chemistry methods for the oxidation reactions in organic synthesis has been an long standing research activity in the research group. This research activity involves also studies of antioxidants and development of new total syntheses of such compounds.
Development and investigation of continuous flow organic synthesis reactor systems is an important long standing project in the group. We have successfully developed a novel approach for flow chemistry that is realized in a milli-reactor platform that we have named multi-jet oscillation disk (MJOD) milli-reactor system.
PET Imaging in Drug Design and Development (PET3D) project - A European Marie Sklodowska-Curie Actions (MSCA) Innovative Training Network (ITN)
Contemporary drug development is rather inefficient and difficult to sustain. To keep drug development affordable, it should become more efficient and rationalized. Molecular imaging can play a pivotal role in changing the landscape of drug design and development and improving the health care system. Positron Emission Tomography (PET) imaging, in particular, is the technology that has the potential to lead this fundamental innovation by providing at a much earlier stage reliable answers to key questions emerging during the care cycle: what and where is the disease? Is the disease accurately targeted by the therapy? Is the treatment effective? By answering the questions above, PET imaging has the capacity to render much more effectively the transition from pre-clinical to clinical phase, and to strongly facilitate the development of better drugs at an earlier stage and in a much more sustainable manner. However, new radiolabelled compounds, so-called tracers, are required to be able to use PET successfully.
The Bergen section of the PET3D consortium shall design, develop and optimize new synthetic methods necessary for the synthesis of new tracers targeting hypoxic tumour tissue, NTR-bioreductive probes, and/or targeted drug delivery. To achieve that we will synthesize and characterize highly functionalized radiolabeled (18F or 11C) 2- and 4-nitroimidazoles and/or other biologically relevant compounds. The novel scaffolds will be investigated as radiotracers at the pre-clinical PET/CT-scanner at Haukeland University Hospital.
KJEM131 Organic Synthesis and Analysis (past)
KJEM232 Experimental Organic Synthesis
KJEM233 Organic mass spectrometry (past)
KJEM335 Physical Organic Chemistry (past)
Organometallic reactions in organic synthesis
Experimental organic synthesis and spectroscopy (project)
N-heterocyclic carbenes in synthesis
Free radical reactions in synthetic organic chemistry
Instrumental methods in organic synthesis
Experimental design and modelling in organic synthesis
- Alexander H. Sandtorv, Karl Wilhelm Törnroos, and Hans-René Bjørsvik.* Stille Cross-Coupling for the Functionalization of the Imidazole Backbone: Revisit, Improvement, and Applications of the Method. Eur. J. Org. Chem. 2015, 3506–3512.
- Alexander H. Sandtorv and Hans-René Bjørsvik.* Controlling the course of a two-way switchable Pd-catalyzed process by means of empirical multivariate models. ChemCatChem 2015, 7, 2196 – 2205.
- Cristian Gambarotti and Hans-René Bjørsvik.* The Baeyer-Villiger oxidation versus aromatic ring hydroxylation: Competing organic peracid oxidation mechanisms explored by multivariate modelling of designed multi-response experiments. Journal of Physical Organic Chemistry 2015, 28, 619-628.
- Alexander H. Sandtorv and Hans-René Bjørsvik.* Scope and Mechanistic Limitations of a Sonogishara Coupling on the Imidazole Backbone. Eur. J. Org. Chem. 2015, 4658-4666.
- Alexander H. Sandtorv, Calum Leitch, Siv Lise Bedringaas, Bjørn Tore Gjertsen and Hans-René Bjørsvik.* Alkylated Silver–N-Heterocyclic Carbene (NHC) Complexes with Cytotoxic Effects in Leukemia Cells. ChemMedChem 2015, 10, 1522 – 1527, (cover)
- Vijayaragavan Elumalai and Hans-René Bjørsvik.* Indium powder as a reducing agent in the synthesis of 2-amino-1,1'-biphenyls. Tetrahedron Letters 2016, 57, 1224–1226.
- Vijayaragavan Elumalai, Alexander H. Sandtorv, and Hans-René Bjørsvik.* A Highly Efficient Pd(PPh3)4-Catalyzed Suzuki Cross-Coupling Method for the Preparation of 2-Nitrobiphenyls from 1-Chloro-2-Nitrobenzenes and Phenylboronic acids. European Journal of Organic Chemistry 2016, 1344-1354.
- Marta Ferreri, Audun Drageset, Cristian Gambarotti, and Hans-René Bjørsvik.* Continuous flow synthesis of the iodination agent 1,3-diiodo-5,5-dimethyl-imidazolidine-2,4-dione telescoped with semi-continuous product isolation. Reaction Chemistry & Engineering 2016, 1, 379-386.
- Audun Drageset and Hans-René Bjørsvik.* Continuous flow synthesis cocatenated with continious flow liquid-liquid extraction for work-up and purification: selective mono- and di-iodination of the imidazole backbone. Reaction Chemistry & Engineering 2016, 1, 436-444.
- Hans-René Bjørsvik* and Vijayaragavan Elumalai.Synthesis of the Carbazole Scaffold Direcly form 2-amino-biphenyl by means of tandem C-H activation and C-N bond formation. European Journal of Organic Chemistry 2016, 5474-5479.
- Vijayaragavan Elumalai and Hans-René Bjørsvik.* A Concise Synthesis to Benzo[c]cinnolines via 2,2´-Dinitro-1,1´-Bienyls Attained from a Novel Tailored Suzuki Cross-Coupling. ChemistrySelect 2017, 2, 9387-9390