Sinteza N-alkil-N-metil-substituiranih enaminonov in njihova uporaba v HAT-fotokataliziranem križnem spajanju s 4-bromobenzonitrilom

Logonder, Maj (author), Grošelj, Uroš (mentor)

V diplomskem delu sem preučeval sintezo enaminonov in njihovo uporabo v reakcijah HAT-fotokataliziranega križnega spajanja z aril bromidi ob uporabi niklja kot kovinskega katalizatorja. Enaminoni so pomembni sintetski intermediati zaradi svoje konjugirane »push–pull« strukture, ki jim daje značilne kemijske lastnosti. Enaminone sem sintetiziral s transaminiranjem (E)-3-(dimetilamino)-1-fenilprop-2-en-1-ona. Sintetizirane enaminone sem nato uporabil v reakcijah križnega spajanja z različnimi aril bromidi. Produkte reakcij sem izoliral ter okarakteriziral z infrardečo spektroskopijo in spektroskopijo jedrske magnetne resonance (¹H in ¹³C NMR). Pri večini reakcij so bili doseženi dobri izkoristki in uspešno potrjene strukture produktov. Rezultati potrjujejo, da HAT-fotokataliza v kombinaciji z nikljevo katalizo predstavlja učinkovito metodo za tvorbo novih vezi C–C iz enaminonov pod blagimi reakcijskimi pogoji ter omogoča sintezo funkcionaliziranih organskih spojin.

• Language: Slovenian
• Keywords: enaminoni, HAT, križno spajanje, aril bromidi, nikelj
• Work type: Bachelor thesis/paper
• Typology: 2.11 - Undergraduate Thesis
• Organization: FKKT - Faculty of Chemistry and Chemical Technology
• Year: 2026
• PID: 20.500.12556/RUL-186614
• COBISS.SI-ID: 292907267
• Publication date in RUL: 03.09.2026

Secondary language

• Language: English
• Title: Synthesis of N-alkyl-N-methyl-substituted enaminones and their application in HAT-photocatalyzed cross-coupling with 4-bromobenzonitrile

Abstract

This thesis focuses on the synthesis of enaminones and their application in HATphotocatalyzed, nickel-mediated cross-coupling reactions with aryl bromides. Enaminones are important synthetic intermediates due to their conjugated push–pull structure, which imparts unique chemical properties. Enaminones were synthesized via transamination of (E)-3-(dimethylamino)-1-phenylprop-2-en-1-one. The synthesized enaminones were subsequently employed in cross-coupling reactions with various aryl bromides. The reaction products were isolated and characterized by infrared spectroscopy and nuclear magnetic resonance (¹H and ¹³C NMR) spectroscopy. Most reactions gave good yields, and the structures of the synthesized products were successfully confirmed. The results demonstrate that HAT photocatalysis combined with nickel catalysis represents an efficient strategy for the formation of new C–C bonds from enaminones under mild reaction conditions and enables the synthesis of functionalized organic compounds.

• Keywords: Enaminones, HAT, cross-coupling, aryl bromides, nickel