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Imidazol kot usmerjajoča skupina v aktivaciji C-H vezi
ID Iskra, Andraž (Author), ID Požgan, Franc (Mentor) More about this mentor... This link opens in a new window

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Abstract
V diplomskem delu sem teoretično predstavil potek klasičnih reakcij križnega spajanja in nato še direktno funkcionalizacijo z uporabo kovinskih katalizatorjev. V eksperimentalnem delu sem se posvetil direktni funkcionalizaciji C–H vezi 1-benzil-2-fenil-1H-imidazola z uporabo rutenijevega katalizatorja. V prvi stopnji sem pripravil 1-benzil-2-fenil-1H-imidazol, ki sem ga nato uporabil v nadaljnjih reakcijah z različnimi aril halidi z različnimi elektrondonorskimi in elektronakceptorskimi substituenti ob prisotnosti [Ru(p-cimen)Cl2]2 katalizatorja. Z namenom ugotavljanja vplivov na potek reakcije sem spreminjal topili vodo in toluen ter dodatek ligandov KOPiv in PPh3. Ugotovil sem, da v vodi dodatek ligandov ni potreben in da se selektivno tvori monosubstituirani produkt. V toluenu je dodatek ligandov potreben, tvori se mono- in disubstituirani produkt. Direktne povezave med vplivom elektrondonorskih ali elektronakceptorskih substituentov in potekom reakcije nisem opazil.

Language:Slovenian
Keywords:C–H aktivacija, funkcionalizacija, 2-fenil-1H-imidazol, ligandi
Work type:Bachelor thesis/paper
Typology:2.11 - Undergraduate Thesis
Organization:FKKT - Faculty of Chemistry and Chemical Technology
Year:2025
PID:20.500.12556/RUL-171943 This link opens in a new window
COBISS.SI-ID:253486339 This link opens in a new window
Publication date in RUL:04.09.2025
Views:159
Downloads:27
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Secondary language

Language:English
Title:Imidazole as directing group in C-H bond activation
Abstract:
In my thesis, I theoretically described the course of classical cross-coupling reactions and then also direct functionalisation using metal catalysts. In the experimental part, I focused on direct functionalisation of C–H bonds using a ruthenium catalyst in the presence of an imidazole directing group. In the first stage, I prepared 1-benzyl-2-phenyl-1H-imidazole, which was then used in further reactions with various aryl halides with different electron-donor or electron-withdrawal properties in the presence of [Ru(p-cimen)Cl2]2 catalyst. To determine the effects on the course of the reaction, I varied the solvents water and toluene as well as addition of ligands KOPiv and PPh3. I found out that in the water the addition of ligands is not necessary and that the monosubstituted product is formed selectively. In toluene, the addition of ligands is necessary, mono- and disubstituted products can be formed. I did not observe any direct correlation between the influence of electron-donor or electron-withdrawal substituents and the course of the reaction.

Keywords:C–H activation, functionalization, 2-phenyl-1H-imidazole, ligands

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