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Pd-catalyzed selective synthesis of arylated aldehydes

Defense Thèse de doctorat : Univ. Genève, 2015 - Sc. 4869 - 2015/09/17
Abstract The aim of this thesis work has been the development of new methodologies for the selective synthesis of arylated aldehydes by means of palladium catalysis. In the last decades, the alpha-arylation of enolizable carbonyl compounds has advanced with significant strides. In this context, aldehydes revealed to be particularly challenging substrates. In the first part of this study, extension of the palladium-catalyzed intermolecular alpha-arylation of aldehydes to alpha,beta-unsaturated aldehydes are presented. This reaction, based on the vinylogous principle, has been applied to the synthesis of gamma-arylated alpha,beta-unsaturated aldehydes bearing a congested gamma-quaternary centers with perfect regioselectivity and good E/Z selectivity. We next described a complementary approach for the synthesis of beta-arylated aldehydes by palladium-catalyzed intermolecular alpha-benzylation of aldehydes. This reaction showed to be remarkably general with respect to both coupling partners. In the last part of this thesis, preliminary results regarding the Heck-Matsuda reaction on allylic and cinnamyl alcohols are discussed.
Keywords PalladiumCatalysisArylationAldehydes
URN: urn:nbn:ch:unige-791015
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Research group Groupe Mazet
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FRANZONI, Ivan. Pd-catalyzed selective synthesis of arylated aldehydes. Université de Genève. Thèse, 2015. https://archive-ouverte.unige.ch/unige:79101

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Deposited on : 2016-01-11

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