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Development of a "Release and Catch" Catalytic System for [2+2+2] Cycloaddition Reactions / submitted by Dominik Krisch
Additional Titles
Entwicklung eines "Release and Catch" Katalysesystems für [2+2+2] Cycloadditions-Reaktionen
AuthorKrisch, Dominik
Thesis advisorHapke, Marko
PublishedLinz, 2019
Description79 Blätter : Illustrationen
Institutional NoteUniversität Linz, Masterarbeit, 2019
Abweichender Titel laut Übersetzung der Verfasserin/des Verfassers
Document typeMaster Thesis
Keywords (EN)catalysis / cycloadditions
URNurn:nbn:at:at-ubl:1-26695 Persistent Identifier (URN)
 The work is publicly available
Development of a "Release and Catch" Catalytic System for [2+2+2] Cycloaddition Reactions [2.57 mb]
Abstract (English)

The intention of this work was the development of a “release and catch” type catalyst for [2+2+2] cycloaddition reactions to make catalyst recycling for this reaction class more convenient and allow for a proof of principle thereof. For this purpose, two novel vinyl-functionalized P ligands, a BINOL derived phosphoramidite and a phosphite were successfully prepared via multi step syntheses after overcoming a variety of obstacles. Starting from CpCo(CO)2 the respective CpCo(P ligand)CO complexes were prepared via thermal ligand exchanges in excellent yields. Yet photochemical substitution of the second CO ligand was not achievable employing our photoreactor, therefore only the CpCo(I)(phosphite)(maleic anhydride) complex could be prepared in the scope of this thesis. With this new complex in hand, a benchmark [2+2+2] cycloaddition reaction was performed and its activity for catalyzing this type of reaction demonstrated. Preparation of the second CpCo(I) complex in addition to studies concerning the recyclability of the precatalysts as well as their envisioned immobilization via copolymerization, however, were unfortunately not feasible in the given timeframe and will be subject of further research. Side projects to synthesize a novel triyne motive for cyclization reactions via Grignard or Barbier type reactions, as well as attempted postfunctionalization of preformed CpCo(I) complexes via Ir catalyzed borylation were unfortunately unsuccessful. However, especially the latter results will be useful for further modifications of the catalytic system to enable such functionalizations in future catalyst generations.

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