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Paladij/rutenij dvojno ariliranje heteroaril kinolinskih derivatov
Rozman, Urša (Author), Štefane, Bogdan (Mentor) More about this mentor... This link opens in a new window

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Abstract
Reakcije funkcionalizacije petčlenskih heterociklov največkrat potečejo na C2 in/ali C5 mestu, medtem ko sta mesti C3 in C4 manj reaktivni. Z uporabo dveh različnih kovin prehoda (rutenij in paladij), smo selektivno funkcionalizirali petčlenske heterocikle s kinolinom kot usmerjajočo skupino. Izvedli smo Ru-katalizirano C‒H ariliranje 2-heteroarilkinolinov ter z rentgensko analizo dokazali, da le-to poteka preko tvorbe petčlenskega rutenacikla. Temu je sledilo nadaljnjo ariliranje heterocikla s Pd-katalizatorjem. Preučili smo regioselektivnost reakcij in poiskali optimalne reakcijske pogoje za posamezno stopnjo neposredne C–H funkcionalizacije za dosego čim višje stopnje pretvorbe do končnih diariliranih produktov. V obeh stopnjah smo reakcije 2-heteroarilkinolinov izvedli z različnimi aril bromidi, ki so vključevali tako elektronprivlačne kot tudi elektrondonorske skupine.

Language:Slovenian
Keywords:kinolin, rutenij katalizirana reakcija, paladij katalizirana reakcija, C‒H aktivacija, sekvenčno neposredno dvojno C–H ariliranje, usmerjajoča skupina
Work type:Master's thesis/paper (mb22)
Tipology:2.09 - Master's Thesis
Organization:FKKT - Faculty of Chemistry and Chemical Technology
Year:2020
COBISS.SI-ID:21070083 This link opens in a new window
Views:549
Downloads:144
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Secondary language

Language:English
Title:Palladium/ruthenium dual arylation of heteroaryl quinoline derivatives
Abstract:
Functionalization of five-membered heteroaromatics generally proceeds at the C2- and/or C5-position, whereas C3- and C4-positions are less reactive. The aim of our work was to selectively functionalize five-membered heterocycles with the use of two different transition metals (ruthenium and palladium) and quinoline as a directing group. We performed Ru-catalyzed C–H arylation of 2-heteroarylquinolines. Additionally, the formation of a five-membered ruthenacycle was proved, which was confirmed by crystal structure analysis of the complex. Further, Pd-catalyzed arylation of heterocycle was carried out. We studied the regioselectivity of the performed reactions and optimized the reaction conditions for each step of the reaction. We wanted to achieve the highest possible conversion to the final diarylated products. In both steps, the reactions of 2-heteroarylquinolines were carried out with different aryl bromides, which included both electron-withdrawing and electron-donating groups.

Keywords:quinoline, ruthenium catalyzed reaction, palladium catalyzed reaction, C‒H activation, sequential direct double C–H arylation, directing group

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