Sinteza akriloil substituiranih biarilov

magistrsko delo

Anita Zupanc (Author), Bogdan Štefane (Mentor), Miha Lukšič (Thesis defence commission member), Krištof Kranjc (Thesis defence commission member)

Abstract

Horner–Wadsworth–Emmonsova (HWE) reakcija je modifikacija Wittigove reakcije, pri kateri se α,β-nenasičeni estri pripravijo iz stabiliziranih fosfonatnih anionov, ki so ustrezno nukleofilni, z aldehidi ali ketoni v prisotnosti ustrezne baze. V sklopu magistrskega dela smo z uporabo pristopa HWE reakcije sintetizirali različne 2- halocinamatne estre. Produkte smo pripravili s spremembo izbire in položaja substituentov na aromatskem obroču 2-haloaril aldehida, kjer so možni substituenti -H, -OCH$_3$, -NO$_2$, -F, -CH$_3$ itd. Zanimalo nas je tudi, kako kombinacije posameznih skupin vplivajo na potek reakcije in posledično določajo optimalne reakcijske pogoje za sintezo želenih spojin. V nadaljevanju smo predhodno pridobljene produkte uporabili pri Suzuki–Miyaurovem navzkrižnem spajanju. Gre za reakcijo med organoborovim reagentom in organskim halidom ali psevdohalidom v prisotnosti paladijevega ali nikljevega katalizatorja in baze. Podrobneje smo se osredotočili na reakcijo navzkrižnega spajanja med različnima 2-formilfenilboronskima kislinama v kombinaciji z zgoraj omenjenimi 2-halocinamatnimi estri. Primarni cilj je bil tvorba nove vezi C–C, ki vodi do nastanka akriloilno substituirane biarilne spojine. Dodatno smo preverili, ali izbrani reagenti vodijo do želenih produktov ter ovrednotili uspešnost reakcij z dobljenimi kvantitativnimi izkoristki.

Keywords

Horner–Wadsworth–Emmonsova reakcija;HWE reakcija;Wittigova reakcija;Suzuki–Miyaurovo navzkrižno spajanje;2-halocinamatni estri;biarili;magistrska dela;

Data

Language:	Slovenian
Year of publishing:	2025
Typology:	2.09 - Master's Thesis
Organization:	UL FKKT - Faculty of Chemistry and Chemical Technology
Publisher:	[A. Zupanc]
UDC:	547.1(043.2)
COBISS:	249628931
Views:	86
Downloads:	21
Average score:	0 (0 votes)
Metadata:

Other data

Secondary language:	English
Secondary title:	Synthesis of acryloyl substituted biaryls
Secondary abstract:	The Horner–Wadsworth–Emmons (HWE) reaction is a modification of the Wittig reaction in which α,β-unsaturated esters are prepared from stabilized phosphonate anions (which are highly nucleophilic) with aldehydes or ketones in the presence of a suitable base. In this thesis, we used the principle of the HWE reaction to synthesize various 2-halocinnamate esters. The products were prepared by changing the choice and position of substituents on the aromatic ring of 2-haloaryl aldehyde, where the possible substituents are -H, -OCH$_3$, -NO$_2$ , -F, -CH$_3$ , etc. Furthermore, we were interested how the combinations of the individual groups influence the course of the reaction and consequently determine the optimal reaction conditions for the synthesis of the desired compounds. Thereafter, the previously obtained products were used in Suzuki–Miyaura cross- coupling. This is a reaction between an organoboron reagent and an organic halide or pseudohalide in the presence of a palladium or nickel catalyst and a base. The study focuses on the cross-coupling reaction between different 2-formylphenylboronic acids in combination with the aforementioned 2-halocinnamate esters. The primary goal is the formation of a new C–C bond leading to the formation of an acryloyl-substituted biaryl compound. Additionally, we checked whether the selected reagents lead to the desired products and evaluated the success of the reactions with the obtained quantitative yields.
Secondary keywords:	HWE reaction;2-halocinnamate esters;Suzuki–Miyaura cross-coupling;biaryls;Organska sinteza (kemija);Kemijske reakcije;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 (49 str.))
ID:	27225071