The research activities of our group are focused on the application of the reactivity of transition metals in the following areas:
Design of new reactions and processes for the preparation of heterocyclic compounds
Research activities associated with the chemistry of heterocyclic compounds can be demonstrated by the synthesis of pentasubstituted phosphols by copper-catalyzed C-H activation of 1,3,4-trisubstituted phospholes:
Polák, P.; Tobrman, T. Formal Transition-Metal-Catalyzed Phosphole C–H Activation for the Synthesis of Pentasubstituted Phospholes.
Org. Lett. 2020, 22, 2187-2190. DOI: 10.1021/acs.orglett.0c00359
Another use of transition-metal-catalyzed reactions is represented by the preparation of trisubstituted pyrroles using a dearomatization strategy:
Polák, P.; Tobrman, T. Dearomatization Strategy for the Synthesis of Arylated 2H-Pyrroles and 2,3,5-Trisubstituted 1H-Pyrroles.
Org. Lett. 2017, 19, 4608-4611. DOI: 10.1021/acs.orglett.7b02219
Cross-coupling reactions of activated C-O bonds for the preparation of tetrasubstituted alkenes
The use of activated C-O bonds is an attractive alternative to organohalogen-based electrophilic templates. From a number of ways to activate C-O bonds, we pay attention to reactivity of enol-phosphates. We have recently published a new methodology for the preparation of tamoxifen that uses enol phosphate as a starting compound:
Kotek, V.; Polák, P.; Dvořáková, H.; Tobrman, T. Aluminium Chloride Promoted Cross-Coupling of Trisubstituted Enol Phosphates with Organozinc Reagents En Route to the Stereoselective Synthesis of Tamoxifen and Its Analogues
Eur. J. Org. Chem. 2016, 5037-5044. DOI: 10.1002/ejoc.201600959
Cross-coupling reactions of activated C-O bonds were also used for the preparation of 2,3-disubstituted-1,3-dienes, [3]- and [4]dendralenes:
Polák, P.; Tobrman, T. Novel Selective Approach to Terminally Substituted [n]Dendralenes.
Eur. J. Org. Chem. 2019, 957-968. DOI:10.1002/ejoc.201801522
We also described the synthesis of biologically active substance starting from enol phosphate:
Polák, P.; Tobrman, T. The synthesis of polysubstituted indoles from 3-bromo-2-indolyl phosphates
Org. Biomol. Chem. 2017, 15, 6233-6241. DOI:10.1039/C7OB01127J