Paladioak katalizaturiko ester aktibatuen bidezko C-H azilazio intramolekularra Fluorenonen sintesirako

Abstract

[EUS] Gradu Amaierako Lan honetan, interes handiko konposatuak diren fluorenonen sintesia burutu egin da. Molekula hauek sintetizatzeko metodo aunitz egon arren, ikertu den metodoa, Pd bidez katalizatutako C-H azilazio intramolekular bat da, substratu bezala azido [1,1 ́-bifenil] karboxilioaren ester aktibatuak, Pd(OAc)2 aurrekatalizatzaile bezala eta PCy3·HBF4 ligando moduan erabiliz. Transformazio intramolekular hau burutu ahal izateko, lehenik eta behin, talde ateragarri ezberdinak dituzten ester aktibatu batzuk prestatu egin dira, aurretik aipatutako erreakzioarekiko beraien erreaktibitatea ikertu nahian. Horrela, fluorenonak sintetizatzeko substratu egokienak zeintzuk diren aztertu da. Behin talde ateragarri optimoa zein den ikusita, substratuaren eraztun aromatikoetan ordezkatzaile ezberdinak jartzeak ziklazio erreakzioan izan ditzakeen efektuak aztertu dira

[ENG] In this Final Degree Project, the synthesis of fluorenones has been carried out. Although there are many methods to synthesize these interesting molecules, the method herein studied consists of a Pd-catalyzed intramolecular C-H acylation, using activated esters derivated from [1,1 ́-biphenyl] carboxyl acid as a substrate, Pd(OAc)2 as a precatalyst and PCy3·HBF4 as a ligand. In order to achieve this intramolecular transformation, firstly the synthesis of some activated esters has been acomplished, bearing different leaving groups, with the aim of studying their reactivity. Thus, the most suitable substrates for the synthesis of fluorenone have been tested. Once the optimal leaving group has been determined, the possible effects of placing different substitutes on the aromatic rings of the substrate in the cyclization reaction have been studied.