000088016 001__ 88016 000088016 005__ 20200224103749.0 000088016 037__ $$aTAZ-TFG-2019-3351 000088016 041__ $$aeng 000088016 1001_ $$aGarcía Abellán, Susana 000088016 24200 $$aC–H activation of indoles for the sustainable synthesis of pharmaceuticals 000088016 24500 $$aC–H activation of indoles for the sustainable synthesis of pharmaceuticals 000088016 260__ $$aZaragoza$$bUniversidad de Zaragoza$$c2019 000088016 506__ $$aby-nc-sa$$bCreative Commons$$c3.0$$uhttp://creativecommons.org/licenses/by-nc-sa/3.0/ 000088016 520__ $$aThis work focuses on the coupling of indoles via C–H activation, due to their importance in bioactive molecules such as pharmaceuticals, for avoiding long synthetic pathways with multiple wasteful reaction septs. This research focuses on the use of oxygen as a green alternative for the oxidation of the Pd-catalyst, which generates H2O as an environmentally harmless side-product. In this work, the Pd-catalyzed C–H/C–H coupling of indoles was demonstrated with oxygen as the oxidant, resulting in a sustainable reaction with H2O as the only stoichiometric by-product. The asymmetric 1,1'-methyl-2,3'-bisindole coupling product was obtained in 88% yield at a low temperature of 40°C. The catalytic activity was increased, allowing a decrease in Pd-loading from 5 to 1 mol% compared to the state-of-the-art. Furthermore, it was shown that the regioselectivity of the reaction can be influenced by changing the electronic properties of the carboxylate ligand. A decrease in reactivity was observed for indole substrates with lower electron density (indole and 1-acetylindole), which indicates that the reaction occurs via an electrophilic attack of the Pd-catalyst.<br /><br /> 000088016 521__ $$aGraduado en Química 000088016 540__ $$aDerechos regulados por licencia Creative Commons 000088016 700__ $$aDe Vos, Dirk$$edir. 000088016 700__ $$aBeckers, Igor$$edir. 000088016 7102_ $$aUniversidad de Zaragoza$$b $$c 000088016 8560_ $$f721604@celes.unizar.es 000088016 8564_ $$s505074$$uhttps://zaguan.unizar.es/record/88016/files/TAZ-TFG-2019-3351.pdf$$yMemoria (eng) 000088016 909CO $$ooai:zaguan.unizar.es:88016$$pdriver$$ptrabajos-fin-grado 000088016 950__ $$a 000088016 951__ $$adeposita:2020-02-24 000088016 980__ $$aTAZ$$bTFG$$cCIEN 000088016 999__ $$a20190917175554.CREATION_DATE