Application of Novel Phosphine Ligands in Palladium-Catalyzed Cross-Coupling Reactions

Christian Torborg

doi:10.18453/rosdok_id00000551

Christian Torborg

Application of Novel Phosphine Ligands in Palladium-Catalyzed Cross-Coupling Reactions

Universität Rostock, 2009

https://doi.org/10.18453/rosdok_id00000551

Abstract: This thesis describes the application of 2-phosphino-N-aryl-heterocycles as ligands in Pd-catalyzed C–C, C–N and C–O bond forming reactions. Based on prior studies, 2-phosphino-N-arylindoles and -pyrrols were found to form efficient catalysts with Pd-salts in the Sonogashira coupling of (hetero)aryl bromides and the Pd-catalyzed monoarylation of ammonia. The novel imidazole-based phosphines were prepared after a modular synthesis and are stable towards air. They were employed in the Pd-catalyzed phenol synthesis, the Heck-Cassar coupling, and the Pd-catalyzed monoarylation of ammonia. Furthermore, mechanistic studies in the Pd-catalyzed hydroxylation were undertaken.

doctoral thesis free access

title:

Application of Novel Phosphine Ligands in Palladium-Catalyzed Cross-Coupling Reactions

contributing persons:

Christian Torborg[VerfasserIn]
	139453555
Matthias Beller , Prof. Dr.[AkademischeR BetreuerIn]
Carsten Bolm , Prof. Dr.[AkademischeR BetreuerIn]

contributing corporate bodies:

Universität Rostock, Mathematisch-Naturwissenschaftliche Fakultät[Grad-verleihende Institution]
	2147083-2

abstract:

This thesis describes the application of 2-phosphino-N-aryl-heterocycles as ligands in Pd-catalyzed C–C, C–N and C–O bond forming reactions. Based on prior studies, 2-phosphino-N-arylindoles and -pyrrols were found to form efficient catalysts with Pd-salts in the Sonogashira coupling of (hetero)aryl bromides and the Pd-catalyzed monoarylation of ammonia. The novel imidazole-based phosphines were prepared after a modular synthesis and are stable towards air. They were employed in the Pd-catalyzed phenol synthesis, the Heck-Cassar coupling, and the Pd-catalyzed monoarylation of ammonia. Furthermore, mechanistic studies in the Pd-catalyzed hydroxylation were undertaken. [English]

In der vorliegenden Dissertation wird die Anwendung von Dialkyl-heteroarylphosphinen als Liganden in palladiumkatalysierten Bindungsknüpfungen beschrieben. Die zuvor beschriebenen Indol- und Pyrrolphosphine wurden erfolgreich in der Sonogashira-Kupplung von Arylbromiden und in der Anilinsynthese eingesetzt. Die neuartigen Imidazolderivate konnten mit einer modularen Synthesemethode dargestellt werden. Mit auf ihnen basierenden Palladium-Katalysatoren konnten Arylhalide effizient sowohl mit Alkinen, als auch mit Wasser und Ammoniak umgesetzt werden. Des weiterten wurden mechanistische Untersuchungen in der palladiumkatalysierten Phenolsynthese durchgeführt. [German]

document type:

doctoral thesis

institution:

Faculty of Mathematics and Natural Sciences

language:

English

subject class (DDC):

540 Chemistry & allied sciences

publication /
production:

Rostock: Universität Rostock

2009

identifiers: