Transition-Metal-Catalyzed C-H activation reactions onto alkenes for the synthesis of heterocycles

Supervised by:
  1. María Nuria Sotomayor Anduiza Director
  2. Maria Esther Lete Exposito Director

Defence university: Universidad del País Vasco - Euskal Herriko Unibertsitatea

Fecha de defensa: 21 January 2021

  1. Jesús Jiménez Barbero Chair
  2. María Luisa Carrillo Fernández Secretary
  3. Ana Carmen Albéniz Jiménez Committee member
  4. Matthias D'hooghe Committee member
  5. Juan Carlos Carretero Gonzálvez Committee member
  1. Química Orgánica e Inorgánica

Type: Thesis

Teseo: 153986 DIALNET lock_openADDI editor


The research work developed in this Ph.D. Thesis is focused on the development of novel methodologiesbased on transition-metal-catalyzed C-H activation/C-C bond formation reactions for the synthesis of avariety of oxygen- and nitrogen-containing heterocycles. The intramolecular Fujiwara-Moritani reactionhas been extended to the synthesis of a number of heterocyclic compounds. The chromane an quinolinecores have been efficiently constructed via 6-exo-trig processes, while 1,2- and 1,4- dihydroquinolinescould be regioselectively obtained via 6-endo-trig cyclizations. The synthesis of indoles by means of the5-exo-trig intramolecular Fujiwara-Moritani reaction has also been achieved. Afterwards, the interest wasfocused on cobalt. In this sense, we have developed the first Cp*Co(III)-catalyzed intramolecularhydroarylation of unactivated olefins to the synthesis of 2,3-dihydrobenzofurans, pyrroloindoles andchromanes through 5-exo-trig and 6-exo-trig cyclization processes using amide-based directing groups.Moreover, it was found that allyl phenyl ether could be used as allylating agents under Cp*Co(III).Besides, a three-month stay was carried out at the University of Manchester under the supervision ofProfessor Igor Larrosa. During this period, the optimization of the Ru(II)-catalyzed ortho-monomethylationof 2-phenylpyridine was performed, using aryltrimethylammonium salts as the methylationagents.