diplomsko delo
Žiga Močnik (Author), Franc Požgan (Mentor)

Abstract

V diplomskem delu sem opisal postopek priprave N-funkcionaliziranih 2-fenil-1H-imidazolov in njihovo orto funkcionalizacijo preko C–H aktivacije v prisotnosti rutenijevih katalizatorjev. Predstavil sem lastnosti 2-fenilimidazola, pripravo N-funkcionaliziranih 2-fenilimidazolov, klasične reakcije križnega spajanja in katalitsko direktno funkcionalizacijo s pomočjo usmerjajočih skupin. Z eksperimentalnim delom sem želel ugotoviti vpliv prisotnosti različnih funkcionalnih skupin na imidazolu pri direktni C–H funkcionalizaciji. V prvi stopnji sem po postopkih iz literature pripravil N-metil, N-etil, N-butil, N-benzil in N-piridilmetil 2-fenil-1H-imidazole. Te produkte sem nato uporabil kot substrate za reakcijo s klorobenzenom v prisotnosi [Ru(p-cimen)Cl$_2$]$_2$ kot katalizatorja. Z namenom optimizacije reakcijskih pogojev sem spreminjal topilo in dodatek ligandov KOPiv in PPh$_3$. Ugotovil sem, da reakcije najbolje potečejo v vodi, dodatek ligandov pa ni potreben. Substituent na imidazolskem substratu pa vpliva na razmerje med mono- in di-substituiranima produktoma.

Keywords

N-substituiran 2-fenilimidazol;C-H funkcionalizacija;usmerjajoča skupina;rutenijev katalizator;diplomska dela;

Data

Language: Slovenian
Year of publishing:
Typology: 2.11 - Undergraduate Thesis
Organization: UL FKKT - Faculty of Chemistry and Chemical Technology
Publisher: [Ž. Močnik]
UDC: 547.78(043.2)
COBISS: 210971651 Link will open in a new window
Views: 105
Downloads: 80
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Other data

Secondary language: English
Secondary title: N-substituted 2-phenylimidazole as a substrate in the catalytic C-H bond functionalization
Secondary abstract: In my thesis, I described the synthesis of N-functionalized 2-pheny-1H-imidazoles and their ortho functionalization via C–H activation with a ruthenium catalyst. I presented the properties of 2-phenylimidazole, synthesis of N-functionalized 2-phenylimidazoles, classic cross coupling reactions and catalytic direct functionalization aided by directing groups, and mechanism of ruthenium-catalyzed reactions. With my experiments I wanted to study the influence of different functional groups on imidazole for direct C–H functionalization. In the first reaction step I synthesized N-substituted substrates with procedures from the literature. I used these products and reacted them with chlorobenzene and [Ru(p-cimen)Cl$_2$]$_2$ catalyst. With the purpose of optimization, I changed the solvents and added ligands KOPiv and PPh$_3$. I found out that the best solvent is water and that there is no need to add ligands. Different functional groups influence the ration of mono- and diarylated products.
Secondary keywords: N-functionalized 2-phenylimidazole;C-H functionalization;directing group;ruthenium catalyst;Organska sinteza (kemija);Imidazoli;Kataliza;Univerzitetna in visokošolska dela;
Type (COBISS): Bachelor thesis/paper
Study programme: 1000373
Embargo end date (OpenAIRE): 1970-01-01
Thesis comment: Univ. v Ljubljani, Fak. za kemijo in kemijsko tehnologijo, UNI Kemija
Pages: 1 spletni vir (1 datoteka PDF (51 str.))
ID: 24892311