20.500.12556/RUL-117122 Paladij/rutenij dvojno ariliranje heteroaril kinolinskih derivatov Palladium/ruthenium dual arylation of heteroaryl quinoline derivatives 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. 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. kinolin rutenij katalizirana reakcija paladij katalizirana reakcija C‒H aktivacija sekvenčno neposredno dvojno C–H ariliranje usmerjajoča skupina quinoline ruthenium catalyzed reaction palladium catalyzed reaction C‒H activation sequential direct double C–H arylation directing group true false false Slovenski jezik Angleški jezik Magistrsko delo/naloga 2020-06-24 15:30:01 2020-06-24 15:30:07 2022-08-29 03:41:18 0000-00-00 00:00:00 2020 0 0 0000-00-00 NiDoloceno NiDoloceno NiDoloceno 0000-00-00 0000-00-00 0000-00-00 6228 21070083 Rozman_Ursa_-_Paladij-rutenij_dvojno_ariliranje_heteroaril_kinolinskih_derivatov.pdf Rozman_Ursa_-_Paladij-rutenij_dvojno_ariliranje_heteroaril_kinolinskih_derivatov.pdf 1 D9E330E66389B0B5EE1706A1BF4B502B 4a3c04a90f6e51bf50b9dc3a2052f583c57048003ef373ed3bb8c876d72f00ad 1ace22c6-a1b9-11eb-a523-00155dcfd717 https://repozitorij.uni-lj.si/Dokument.php?lang=slv&id=130921 Fakulteta za kemijo in kemijsko tehnologijo 0 0 0