Research on the project involved ARRS-funded Young researchers, doctoral students who are not in the ARRS Young researcher program, and master's and graduate students. In his dissertation entitled "Dual Role of Palladium Catalyst in Alkynylation of Aryl Halides", Dr. Bruno Aleksander Martek (Young researcher, mentor J. Košmrlj) used a systematic analytical approach to identify two palladium species that simultaneously participate in the Sonogashira cross-coupling reactions. One of the palladium key species is based on a pyridine-functionalized 1,2,3-triazol-5-ylidene-N-heterocyclic carbene ligand (Py-tzNHC). The system thus defined allows a wide range of reactants, including those traditionally considered non-reactive, to be combined with low palladium input. This is a practical application of theoretical findings, a conceptually completely new way of carrying out the Sonogashira reaction, which now allows a much more ecologically and economically advantageous synthesis. Dr. Mateja Mihelač (mentor: group member M. Gazvoda) in her dissertation entitled "C–N and C–F bond formation catalyzed by a mesoionic palladium complex" prepared and studied the palladium complex with two different ligands, Py-tzNHC and phenanthroline. The palladium in this complex reacts with an electrophilic fluorinating reagent to form a reactive palladium(IV) fluorine complex that can fluorinate electron-deficient aromatic systems. The PhD was funded by this project (not part of ARRS Young researcher scheme).
D.09 Tutoring for postgraduate students
COBISS.SI-ID: 32160515In 2020, Miha Virant received Krka Grand Prize for his dissertation entitled "Development of homogeneous palladium catalytic systems for selected transformations of terminal acetylenes" (https://www.krkinenagrade.si/o-krkinih-nagradah/simpozij-in-razglasitev-2020-10/) [COBISS.SI-ID 61823491]. Dr. Miha Viranta 's dissertation (mentor J. Košmrlj) contributes to understanding and improving the efficiency of some homogeneous palladium-based catalysts through the thoughtful design of a ligand surrounding the metal. Thus, in addition to the N-heterocyclic carbene base that stabilizes the palladium, the newly developed bidentate ligand also has a labile coordinative pyridine that activates the reactant at the right time in the catalytic process. The action of such an advanced catalyst, reminiscent of the action of an enzyme, has been shown to be crucial for the hydroamination of terminal acetylenes to imines. The development of this catalyst has contributed significantly to the understanding of several other catalytic processes, such as the coupling of terminal acetylenes with aryl halides to form Sonogashira internal acetylenes.
E.01 National awards
COBISS.SI-ID: 303177472On invitation from The Slovenian Chemical Society, in a keynote lecture at the Slovenian Chemical Days conference in September 2019, J. Košmrlj presented some of the results of his research team on the development of new triazole-based ligands.
B.04 Guest lecture
COBISS.SI-ID: 1538415043On invitation of the Organizing Committee of the 47th conference “Synthesis and Analysis of Drugs” (Syntéza a Analýza Léčiv), J. Košmrlj presented some results of the project in invited lecture entitled “Recent advances in the Sonogashira reaction”, which took place in September 2018 in Brno. The conference is for 50 years traditional central European meeting for sharing current topics and knowledge in the field of synthesis and analysis of drugs not only for scientists from universities and other scientific institution but also for people from pharma industry and other companies. The conference was a part of the celebration of the 100th anniversary of the establishment of the University of Veterinary and Pharmaceutical Sciences Brno. Other relevant lectures: In the frame of the plenary lecture at The Conference on the 65th Anniversary of Faculty of Pharmacy, Comenius University in Bratislava and 46th EuroCongress on Drug Synthesis and Analysis in Bratislava J. Košmrlj presented recent research work of his group in Ljubljana in the fields of drug synthesis and cross-coupling reactions. The title of the lecture was »Targeting some diseases and disorders: an organic chemist's perspective [COBISS.SI-ID 1537505731]. M. Gazvoda, Recent advances on mechanistic studies of palladium catalyzed alkynylation and hydroamination (Blue Danube lecture), 18th Blue Danube Symposium on Heterocyclic Chemistry, 2019, Ljubljana, Slovenia [COBISS.SI-ID 1538372291]. M. Gazvoda, M. Krivec, Z. Časar, J. Košmrlj, Dead ends and detours in preparation of a pharmaceutically important 2-(cyclobuten-1-yl)-1H-indole scaffold (invited lecture), 47th Conference Synthesis and Analysis of Drugs, 2018, Brno, Czech Republic [COBISS.SI-ID 1537998019].
B.04 Guest lecture
COBISS.SI-ID: 1537894595Ana Siljanovska received the prestigious University Prešeren Award for her master thesis, which she completed under the mentorship of J. Košmrlj. The research work was part of the project.
E.01 National awards
COBISS.SI-ID: 27825667