Reacciones de hidroarilación e hidroalcoxilación de alquinos catalizadas por indio (III)aplicaciones en la síntesis de 2H-cromenos, 1,2-dihidroquinolinas y benzo[b]furanos

  1. Alonso Marañón, Lorena
Supervised by:
  1. José Pérez Sestelo Co-director
  2. M. Montserrat Martínez Co-director

Defence university: Universidade da Coruña

Fecha de defensa: 13 April 2018

Committee:
  1. María del Carmen Torre Egido Chair
  2. Jaime Rodríguez Secretary
  3. Robert Edward Maleczka Committee member

Type: Thesis

Teseo: 543354 DIALNET lock_openRUC editor

Abstract

In this PhD Thesis, the research developed about indium-catalyzed intramolecular hydroarylation, hydroamination and hydroalkoxylation reactions and their application to the synthesis of heterocyclic compounds is presented. In the first place, the formation of carbon–carbon bonds in regioselective intramolecular hydroarylation reactions of aryl propargyl ethers is studied. Sequential processes involving indium-catalyzed hydroarylation–palladium-catalyzed crosscoupling reactions where the formation of two carbon–carbon bonds are formed in “one-pot” were developed. Finally, cascade 6-endo cycloisomerization reactions of aryl propargyl ethers diyne derivatives affording naphtho[c]chromenes using only 5 mol% of indium(III) catalyst were studied. In the second chapter of the Thesis, the formation of carbon–nitrogen and carbon–oxygen bonds in indium(III)-catalyzed intramolecular hydroamination and hydroalkoxylation reactions was studied obtaining nitrogen and oxygen heterocycles such as 1,2-dihydroquinolines, isoquinolines, indols and benzo[b]furans regioselectively.