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Direct arylation and its application in supramolecular polymer synthesis
Loukotová, Lenka
This thesis is divided into two parts. In the first part there is reported palladium- catalysed regioselective direct arylation of benzofurans with arylsulfonyl chlorides as the coupling partner to C2 carbon. The best reaction conditions of this reaction were investigated, then the influence of various arylsulfonyl chloride substituents to the reaction and finally it is reported direct arylation of C2-arylated benzofuran to C3 carbon to give diarylated benzofuran with different aryl substituents. In the second part, there is reported the synthesis of 2-(hydroxymethyl)-5,7-bis{5- [(2,2':6',2''-terpyridine)-4'-yl]thiophen-2-yl}-2,3-dihydrothieno[3,4-b][1,4]dioxin and modification of its sidechain. As a starting material of the synthesis it was used commercially available 4'-bromo-(2,2':6',2''-terpyridine). The synthetic sub-steps included Suzuki cross- coupling, bromination and C-H bond activation. Then it was also reported the complexation of synthesized oligomer with zinc and iron cations.
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Cyclodextrin derivatives for construction of supramolecular dendrimers
Kouřilová, Ema ; Jindřich, Jindřich (advisor) ; Veselý, Jan (referee)
This bachelor thesis deals with the synthesis of derivatives of α-, β- and γ-cyclodextrins which are potentially usable for the supramolecular dendrimers construction. These dendrimers could be used in medicinal chemistry as carriers of drugs or in other areas of chemistry as well. Firstly, the tosyloxy group of mono-6-O-tosylates of cyclodextrins was substituted with cyanoarylphenolates and then the intermediate permethylated at the remaining hydroxy groups. As reactants for monosubstitutions, 4-hydroxybenzonitrile and 4'-hydroxy-[1,1'-biphenyl]-4-carbonitrile were chosen. The reagent used for permethylations was iodomethane. In the last phase, attempts to trimerize the cyano groups of the permethylated derivatives under basic and acidic conditions were made, but the wanted product was not obtained. Key words: cyclodextrin, monosubstitution, dendrimer, nitrile trimerization, supramolecular polymers
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Direct arylation and its application in supramolecular polymer synthesis
Loukotová, Lenka
This thesis is divided into two parts. In the first part there is reported palladium- catalysed regioselective direct arylation of benzofurans with arylsulfonyl chlorides as the coupling partner to C2 carbon. The best reaction conditions of this reaction were investigated, then the influence of various arylsulfonyl chloride substituents to the reaction and finally it is reported direct arylation of C2-arylated benzofuran to C3 carbon to give diarylated benzofuran with different aryl substituents. In the second part, there is reported the synthesis of 2-(hydroxymethyl)-5,7-bis{5- [(2,2':6',2''-terpyridine)-4'-yl]thiophen-2-yl}-2,3-dihydrothieno[3,4-b][1,4]dioxin and modification of its sidechain. As a starting material of the synthesis it was used commercially available 4'-bromo-(2,2':6',2''-terpyridine). The synthetic sub-steps included Suzuki cross- coupling, bromination and C-H bond activation. Then it was also reported the complexation of synthesized oligomer with zinc and iron cations.
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Direct arylation and its application in supramolecular polymer synthesis
Loukotová, Lenka ; Svoboda, Jan (advisor) ; Drahoňovský, Dušan (referee)
This thesis is divided into two parts. In the first part there is reported palladium- catalysed regioselective direct arylation of benzofurans with arylsulfonyl chlorides as the coupling partner to C2 carbon. The best reaction conditions of this reaction were investigated, then the influence of various arylsulfonyl chloride substituents to the reaction and finally it is reported direct arylation of C2-arylated benzofuran to C3 carbon to give diarylated benzofuran with different aryl substituents. In the second part, there is reported the synthesis of 2-(hydroxymethyl)-5,7-bis{5- [(2,2':6',2''-terpyridine)-4'-yl]thiophen-2-yl}-2,3-dihydrothieno[3,4-b][1,4]dioxin and modification of its sidechain. As a starting material of the synthesis it was used commercially available 4'-bromo-(2,2':6',2''-terpyridine). The synthetic sub-steps included Suzuki cross- coupling, bromination and C-H bond activation. Then it was also reported the complexation of synthesized oligomer with zinc and iron cations.
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