Martin Kotora, Department of Organic Chemistry, Faculty of Science, Charles University, Czech Republic

"Catalysis and Skeletal Editing: A Route to Aromatic Compounds"

Abstract

A combination of catalysis and skeletal editing offers a powerful tool for synthesis of molecules with complex molecular scaffolds. Specifically, it could be used for converting of various molecules to various aromatic and heteroaromatic substances. In this presentation I would like to demonstrate that catalytic cyclotrimerization1,2 of suitably substituted triynes gives rise to helical compounds possessing the indeno[2,1-c]fluorenedione moiety3,4 that can be transformed into heterohelicenes or helicenes by using Schmidt or Büchner−Curtius−Schlotterbeck5,6 reactions, respectively. In cases of enantioselective cyclotrimerization,2 transformation of highly enantioenriched helical diketones (up to 99% ee) yields corresponding chiral helicenes and heterohelicenes without erosion of enantiopurity.3 Appropriate reaction conditions for each transformation and chirooptical properties of the obtained enantiomers will be discussed as well.

References:

1. Kaiser, R. P.; Nečas, D.; Cadart, T.; Gyepes, R.; Císařová, I.; Mosinger, J.; Pospíšil, L.; Kotora, M. Angew. Chem. Int. Ed. 2019, 58, 17169–17174.

2. Cadart, T.; Nečas, D.; Kaiser, R. P.; Favereau, L.; Císařová, I.; Gyepes, R.; Hodačová, J.; Kalíková, K.; Bednárová, L.; Crassous, J.; Kotora, M Chem. Eur. J. 2021, 27, 11279–11284.

3. Cadart, T.; Feriancová, L.; Henke, P.; Gyepes, G.; Císařová, I.; Kalíková, K.; Kotora, M. Chem. Commun. 2025, 61, 4662–4665.

4. Bogomolec. M.; Feriancová, L.; Ortiz, J. S. O.; Crassous, J.; Císařová, I.; Gyepes, R.; Cadart, T.; Kotora, M. J. Org. Chem. 2025, accepted.

5. Degač, M.; Reininger, L.; Schardax, H.; Andris, E.; Rulíšek, L.; Císařová, I.; Rinner, U.; Cadart, T.; Kotora, M. JACS Au 2025, 5, 4788–4798.

6. Kiss, A.; Feriancová, L.; Gyepes, R.; Cadart, T.; Kotora, M. Appl. Organomet Chem. 2024, 38, e7621.

A short biography with photo

Martin Kotora is a Professor at the Department of Organic Chemistry, Charles University (Prague). His background is in organic chemistry and catalysis. Prior to the current position he obtained his PhD from the Institute of Chemical Process Fundamentals, Czechoslovak

Academy of Sciences in 1991. He completed postdoctoral positions at Institute for Molecular Science (1993-1995, Okazaki, Japan) and Purdue University (1995-1996, Indiana, USA). In 1996 he was appointed as an associate Professor in Catalysis Research Center, Hokkaido

university (Japan). Since 2000 he has been with Charles University. His research interests encompass development and application of transition metal catalyzed reactions, organocatalysis, enantioselective processes.