This work of thesis describes the results obtained from the study of gold-catalyzed synthesis or functionalization reactions or heteroarenes. The work is presented in four different chapters. The first chapter summarizes the most representative reactivity trends in the field of gold catalysis and serves as general introduction. The second chapter is focused on the cycloaddition reaction of 2-vinylindoles with enones towards the preparation of tetrahydrocarbazole derivatives. This process has been studies using classic Lewis acids and gold complexes as catalysts. According to the results, gold catalysts proved more efficient to accomplish the transformation. In the third chapter, a study on gold-catalyzed cycloaddition reactions of 2-vinylindoles with allene derivatives is presented. This work has allowed to identify two different reaction pathways, a formal 4+2 cycloaddition and a multicomponent reaction, both leading to different tetrahydrocarbazole derivatives. The reaction outcome can be controlled with the judicious choice of the reaction conditions. The forth chapter is devoted to the study of gold- and to less extend silver-catalyzed reactions of indoles with dehydroaminoacis. This study has enabled the discovery of a new reactivity of this substrates. The reaction involves the formation of α-indolylacrilate derivatives.
|Titolo:||GOLD-CATALYZED SYNTHESIS AND FUNCTIONALIZATION OF HETEROARENES|
|Data di pubblicazione:||24-feb-2014|
|Parole Chiave:||organic chemistry ; synthesis ; catalysis ; gold ; heterocycles|
|Settore Scientifico Disciplinare:||Settore CHIM/06 - Chimica Organica|
|Citazione:||GOLD-CATALYZED SYNTHESIS AND FUNCTIONALIZATION OF HETEROARENES ; tutor: E. Rossi, R. Vicente. - Milano : Università degli studi di Milano. DIPARTIMENTO DI SCIENZE FARMACEUTICHE, 2014 Feb 24. ((26. ciclo|
|Digital Object Identifier (DOI):||10.13130/pirovano-valentina_phd2014-02-24|
|Appare nelle tipologie:||Tesi di dottorato|