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Transition metal catalyzed cross-coupling reactions of onium salts
Hidasová, Denisa ; Šrogl, Jiří (advisor) ; Drahoňovský, Dušan (referee)
The research of this thesis is focused on developing Suzuki cross-coupling reactions of various onium salts using the catalytic system Ni complex/trans-N,N'-dimethyl-1,2- cyklohexanediamine. As an expansion in the catalysis of nickel compounds, we have established that the catalytic system Ni(cod)2/trans-N,N'-dimethyl-1,2-cyklohexanediamine can affect Suzuki reactions of tetramethylenesulfonium salts with boronic acid, which leads to cleavage of C-S and formation of new C-C bonds under relatively mild reaction conditions. This explains the unique reactivity and biomimetic behavior of a nickel catalyst to activate the C-S bond. Key words: onium salts, Suzuki coupling, nickel complexes
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Cross-coupling reactions of organosulfur compounds
Martínek, Marek ; Šrogl, Jiří (advisor) ; Kotora, Martin (referee)
Cross-coupling reactions are one of the most utilitzed and investigated methods for carbon-carbon bond formation. In this diploma thesis the transition metal catalyzed cross-coupling protocol of organosulfur compounds and boronic acids has been studied. The first part of the thesis is aimed at developing a synthesis of a new heterocyclic compounds, which have been used in the cross-coupling reaction. The second part describes the study of the Liebeskind-Šrogl coupling-inspired reaction itself. Various reaction conditions, catalysts and the influence of the structure of starting materials have been examined.
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Cyclization Reactions Mediated by Transition Metals
Matoušová, Eliška ; Pour, Milan (advisor) ; Bureš, Filip (referee) ; Šrogl, Jiří (referee)
Charles University in Prague, Faculty of Pharmacy in Hradec Králové Department of inorganic and organic chemistry Candidate: Mgr. Eliška Matoušová Supervisor: prof. RNDr. Milan Pour, PhD. Title of Doctoral Thesis: Cyclization reactions mediated by transition metals Within the framework of this Thesis, several analogues of naturally occurring biologically active pyranones were prepared. The synthetic procedure was based on a Pd-cata- lyzed carbopalladation of enyne precursors with subsequent lactonization. Employing this method, bicyclic pentenolides containing fused nitrogen heterocycle as well as carbocycle were synthesized. The preparation of the corresponding oxygen-containing derivative was not successful. The compounds were tested for their antifungal, anitibacterial and cytostatic activity. The second part of the Thesis deals with synthesis of furans and dihydropyrans via palladium and gold catalysis. A highly efficient method for AuI -catalyzed cyclization of propargyl vinyl ethers to dihydropyrans was developed using tris(2-furyl)phosphine as a ligand and methanol as a nucleophile. This method was employed for the preparation of 15 dihydropyran derivatives in high yields. In the absence of a nucleophile furans were formed in lower yields. Dihydropyrans undergo an as yet undescribed...
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Transition metal catalyzed cross-coupling reactions of onium salts
Hidasová, Denisa ; Šrogl, Jiří (advisor) ; Drahoňovský, Dušan (referee)
The research of this thesis is focused on developing Suzuki cross-coupling reactions of various onium salts using the catalytic system Ni complex/trans-N,N'-dimethyl-1,2- cyklohexanediamine. As an expansion in the catalysis of nickel compounds, we have established that the catalytic system Ni(cod)2/trans-N,N'-dimethyl-1,2-cyklohexanediamine can affect Suzuki reactions of tetramethylenesulfonium salts with boronic acid, which leads to cleavage of C-S and formation of new C-C bonds under relatively mild reaction conditions. This explains the unique reactivity and biomimetic behavior of a nickel catalyst to activate the C-S bond. Key words: onium salts, Suzuki coupling, nickel complexes
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Cross-coupling reactions of organosulfur compounds
Martínek, Marek ; Šrogl, Jiří (advisor) ; Kotora, Martin (referee)
Cross-coupling reactions are one of the most utilitzed and investigated methods for carbon-carbon bond formation. In this diploma thesis the transition metal catalyzed cross-coupling protocol of organosulfur compounds and boronic acids has been studied. The first part of the thesis is aimed at developing a synthesis of a new heterocyclic compounds, which have been used in the cross-coupling reaction. The second part describes the study of the Liebeskind-Šrogl coupling-inspired reaction itself. Various reaction conditions, catalysts and the influence of the structure of starting materials have been examined.
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