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Pospeševanje Sonogashirove reakcije brez bakra s pomočjo organokovinskih katalizatorjev
ID Žnideršič, Nika (Author), ID Gazvoda, Martin (Mentor) More about this mentor... This link opens in a new window

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Abstract
V sklopu magistrskega dela smo se ukvarjali z optimizacijo Sonogashirove reakcije spajanja brez bakra. Natančneje, želeli smo pospešiti ključno stopnjo reakcije, transmetalacijo. Neodvisno smo pripravili dva reakcijska intermediata, paladijev oksidativni adukt in paladijev acetilid. Z njima smo izvedli reakcijo transmetalacije, pri tem smo dodajali različne aditive in spremljali njihov vpliv na hitrost transmetalacije. Aditive, ki so kazali ugoden učinek, smo uporabili za pospešitev katalitskih reakcij med aril halidi in terminalnimi alkini. Preučevali smo tudi reaktivnost različnih borovih kislin in terminalnih alkinov pri reakciji spajanja s halogeniranimi acetileni, kjer smo uspešno prišli do želenih produktov. Sintetizirali smo terminalni alkin, ki vsebuje 15N označen piridinski obroč. Le-ta lahko vstopa v Sonogashira reakcijo spajanja kot eden izmed reaktantov.

Language:Slovenian
Keywords:Sonogashirova reakcija brez bakra, transmetalacija, organokovinska kemija, pospeševanje reakcij spajanja
Work type:Master's thesis/paper
Typology:2.09 - Master's Thesis
Organization:FKKT - Faculty of Chemistry and Chemical Technology
Year:2022
PID:20.500.12556/RUL-135372 This link opens in a new window
COBISS.SI-ID:100528131 This link opens in a new window
Publication date in RUL:09.03.2022
Views:1658
Downloads:137
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Secondary language

Language:English
Title:Accelerating copper-free Sonogashira reaction with organometallic catalysts
Abstract:
This master's thesis describes attempts of optimization of copper-free Sonogashira cross-coupling reaction. Namely, we aimed to accelerate the reaction by accellerating its key step, transmetallation. Two reaction intermediates, the oxidative palladium adduct and the palladium acetylide, were prepared independently. We performed the transmetallation reaction between these two complexes and added different additives to study their influence on the rate of transmetallation. Additives that showed a positive effect were used to accelerate the catalytic reactions between aryl halides and terminal alkynes. We also investigated the reactivity of various boric acids and terminal alkynes in the palladium-catalyzed coupling reaction with halogenated acetylenes, which led to the desired products. A terminal alkyne containing a 15N-labeled pyridine ring was synthesized. The latter can enter the Sonogashira coupling reaction as one of the reactants.

Keywords:copper-free Sonogashira reaction, transmetallation, organometallic chemistry, acceleration of coupling reactions

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