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ISBN 978-3-8439-1779-7

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978-3-8439-1779-7, Reihe Organische Chemie

Marc-André Müller
Study of Chiral Iridium N,P Ligand Complexes as Catalysts for the Asymmetric Hydrogenation of Different Substrate Classes

410 Seiten, Dissertation Universität Basel (2014), Softcover, A5

Zusammenfassung / Abstract

The objective of this thesis was the synthesis and further development of different iridium N,P ligand complexes as well as the evaluation and application of different challenging substrate classes in the asymmetric hydrogenation using iridium-based catalysts.

The first chapter of this thesis deals with the further development of bicyclic pyridine-based ligands. A late stage Suzuki-Miyaura cross-coupling allowed for the synthesis of a large variety of different ligands for which a phenyl group was exchanged with more sterically demanding aryl-group. Iridium complexes of these new ligandss emerged as efficient catalysts for the asymmetric hydrogenation of different functionalized and unfunctionalized olefins.

Another substrate class which was investigated in the course of this PhD thesis are vinyl bromides. Established iridium-based catalysts turned out to be extremely unreactive in the hydrogenation of this substrate class. Only terminal vinyl bromides revealed a certain reactivity. As best results, up to >99% conversion with 72% enantiomeric excess was observed