Katalitska funkcionalizacija C-H vezi 2-fenilimidazola

Grošelj, Lena (author), Požgan, Franc (mentor)

V diplomskem delu sem opisala potek direktne funkcionalizacije C–H vezi, katalizirane z rutenijevimi katalizatorji. Predstavila sem način, pri katerem s pomočjo usmerjajočih skupin zagotovimo regioselektivnost C–H funkcionalizacije. S svojimi eksperimenti sem želela z rutenijevim katalizatorjem izvesti direktno arilacijo orto mesta 2-fenilimidazola s pomočjo imidazolnega obroča kot usmerjajoče skupine. Kot arilirne reagente sem uporabila različne aril halide in fenilboronsko kislino. Z namenom, da bi optimizirala reakcijske pogoje, sem spreminjala temperaturo in čas segrevanja reakcij. Pokazala sem, da višja temperatura in daljši čas gretja pozitivno vplivata na potek reakcije, razen v primeru uporabe fenilboronske kisline kot arilirnega reagenta. Ugotovila sem, da reakcija poteče bolje, kadar rutenijevim katalizatorjem dodam kokatalizatorje (uporabila sem KOPiv in PPh3). To so spojine, ki se koordinirajo na rutenij in tako tvorijo katalitski kompleks, ki lažje in bolj učinkovito reagira z izhodnimi spojinami.

• Language: Slovenian
• Keywords: C–H funkcionalizacija, usmerjajoča skupina, rutenijev katalizator, 2-fenilimidazol
• Work type: Bachelor thesis/paper
• Typology: 2.11 - Undergraduate Thesis
• Organization: FKKT - Faculty of Chemistry and Chemical Technology
• Year: 2023
• PID: 20.500.12556/RUL-149514
• COBISS.SI-ID: 162953475
• Publication date in RUL: 07.09.2023

Secondary language

• Language: English
• Title: Catalytic functionalization of the 2-phenylimidazole C-H bonds

Abstract

In my thesis, I described the direct functionalization of C–H bond catalyzed by ruthenium catalysts. I presented a way we can ensure the regioselectivity of C–H functionalization with the help of directing groups. With my experiments, I wanted to carry out direct arylation of the ortho site of 2-phenylimidazole with a ruthenium catalyst and with the help of the imidazole ring as a directing group. I used various aryl halides and phenylboronic acid as arylating reagents. With the purpose to optimize the conditions, I changed the temperature and heating time of the reactions. I showed that a higher temperature and a longer heating time have a positive effect on the course of the reaction, except in the case of using phenylboronic acid as arylating reagent. I found out that to ensure a more favorable course of reaction, I need to add cocatalysts to ruthenium catalysts (KOPiv and PPh3). Those compounds coordinate to ruthenium and thus form a catalyst complex, which then efficiently reacts with the starting compounds.

• Keywords: C–H functionalization, directing group, ruthenium catalyst, 2-phenylimidazole