magistrsko delo
Jakob Muhič (Author), Martin Gazvoda (Mentor), Jurij Lah (Thesis defence commission member), Krištof Kranjc (Thesis defence commission member)

Abstract

Namen raziskovalnega dela je bilo preučevanje tandemske reakcije spajanja med različnimi substituiranimi stireni in halogeniranimi benzaldehidi v prisotnosti nikljevega katalizatorja pri reduktivnih pogojih in v inertni atmosferi. Opisana reakcija poteka v dveh zaporednih korakih, ki potečeta v isti reakcijski zmesi. Izkoristili smo nastanek nikljevega hidrida preko nikljevega katalizatorja pri reduktivnih pogojih. Hidrid se koordinira na dvojno vez stirena, ki dalje reagira s halogeniranim benzaldehidom do nastanka nove C─C vezi, hkrati pa se eliminira halogeniran nikljev kompleks. Iz produkta spajanja z redukcijo karbonilne skupine nastane končni benzilni alkohol s pripetim arilnim obročem, prav tako preko benzilne skupine. Uspeli smo sintetizirati 5 novih strukturno kompleksnih produktov v 10 neodvisnih kombinacijah stirenov in halogeniranih aldehidov. Poleg tega smo posvetili del naloge optimizaciji reakcijskih pogojev in izolaciji produktov za dosego čim višjih celokupnih izkoristkov procesa. Vse produkte smo ustrezno karakterizirali s $^1$H NMR, $^{13}$C NMR, IR- spektroskopskimi in HRMS-analizami.

Keywords

tandemske reakcije;hidroariliranje;organokovinska kataliza;nikljeva kataliza;magistrska dela;

Data

Language: Slovenian
Year of publishing:
Typology: 2.09 - Master's Thesis
Organization: UL FKKT - Faculty of Chemistry and Chemical Technology
Publisher: [J. Muhič]
UDC: 547.538:547.571:544.47(043.2)
COBISS: 228210179 Link will open in a new window
Views: 86
Downloads: 33
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Other data

Secondary language: English
Secondary title: Nickel catalyzed hydroarylation of styrenes with halogenated aromatic aldehydes
Secondary abstract: The aim of this master thesis was to study the tandem reaction, which consists of the coupling between styrenes and halogenated benzaldehydes, and subsequent reduction of aldehyde to alcohol. The reactions were carried out in the presence of a nickel catalyst under reductive conditions and an inert atmosphere where the two described sequential reactions both occurr within the same reaction mixture. We utilized the formation of a nickel hydride via a nickel catalyst under reductive conditions. This hydride coordinates to the double bond of styrene, which then reacts further with the halogenated benzaldehyde to form a new C─C bond and eliminate and regenerate a halogenated nickel complex. The coupling intermediate then undergoes successive reduction of the carbonyl group to the final benzyl alcohol with a benzyl-attached aryl ring. We have successfully synthesized 5 new structurally complex products in 10 independent combinations of styrenes and halogenated aldehydes. Additionally, part of the work focused on the optimization of the reaction conditions and product isolation to maximize the overall yield of the process. Finally, all products were adequately characterized using $^1$H NMR, $^{13}$C NMR, IR spectroscopy, and HRMS analyses.
Secondary keywords: nickel;catalyst;styrene;benzaldehyde;tandem reaction;hydroarylation;Katalizatorji;Nikelj;Stiren;Benzaldehid;Univerzitetna in visokošolska dela;
Type (COBISS): Master's thesis/paper
Study programme: 1000375
Embargo end date (OpenAIRE): 1970-01-01
Thesis comment: Univ. v Ljubljani, Fak. za kemijo in kemijsko tehnologijo, smer Kemija
Pages: 1 spletni vir (1 datoteka PDF (78 str.))
ID: 25943794