Novel aza-arylphosphane ligands for ruthenium catalyzed anti-Markovnikov hydration of terminal alkynes

Within this thesis, straightforward and modular synthetic pathways were developed which allow the synthesis of C6-tert-alkyl- and C6-aryl-pyridylphosphanes, as well as selected aza-arylphosphanes with different substitution pattern by newly developed copper- or nickel-catalyzed cross-coupling reactions. In a second part, these new phosphanes were used as ligands (L) for the synthesis of various complexes of the type [CpRu(L)2(CH3CN)]PF6. Their application as catalysts for the anti-MARKOVNIKOV hydration of terminal alkynes was examined. Kinetic studies were performed in order to explore the structure-activity relationship of the ligands with the ultimate goal to identify highly active catalysts. Subsequently, the most effective catalysts were used for the hydration of various functionalized terminal alkynes, e.g. ketones, malonates, esters. In addition, a new synthetic entry into ß-amino carbonyls has been developed by means of ruthenium-catalyzed anti-MARKOVNIKOV hydration of N-tosyl propargylamines. Finally, the first ruthenium-catalyzed anti-MARKOVNIKOV hydration of terminal alkynes has been described by microwave activation.

Grantor dc:publisher

Publikationsserver der RWTH Aachen University

Year dc:date

2007

Author dc:creator

• Labonne, Aurélie

Contributors dc:contributor

• Bolm, Carsten

• info:eu-repo/classification/ddc/540
• Atom-Ökonomie
• Anti-Markovnikov
• aza-Arylphosphane
• Kreuzkupplung
• Ruthenium-Komplexe
• Chemie
• Atom-economy
• cross-coupling
• ruthenium-complexes

Statement dc:rights

• info:eu-repo/semantics/openAccess

Language dc:language

eng

Identifier

https://publications.rwth-aachen.de/search?p=id:%22RWTH-CONV-124004%22

OAI identifier oai:identifier

oai:publications.rwth-aachen.de:62435