Linnebank, P.R.

English

In this thesis supramolecular strategies were investigated to obtain control over the regioselectivity in the hydroformylation reaction. In the hydroformylation reaction a double bond is reacted with syngas mixture (H2:CO) in the presence of a transition metal catalyst. Since the aldehyde can add on both sides of the double bond, this reaction has an inherent regioselectivity problem. Ligands can be coordinated to the catalytically active metal center to obtain control over the regioselectivity. This strategy is however not always successful and therefore supramolecular strategies were used in this thesis to obtain control over the regioselectivity for substrates that are difficult to control via traditional strategies in homogeneous catalysis. One strategy involves hydrogen bonding of the substrate to the catalyst to restrict the movement of the substrate during the reaction. Another strategy that is used involves the use of a supramolecular capsule around the metal center. For both strategies, the substrate movement is restricted and as a result the regioselectivity is controlled. Chapter 2 describes a computational investigation for why the hydrogen bonding based catalyst gives the regioisomeric outcome that is observed catalytically. Chapter 3 demonstrates first the regioselective conversion of natural fatty acids in the hydroformylation reaction with a tailor made ligand. Chapter 4 describes the a novel class of ligands for regioselective conversions via hydrogen bonding. Chapter 5 reports how the regioselectivity control of a catalyst varies when structural elements of substrates are varied. Chapter 6 investigates if descriptors of the substrate can be used to predict the regioselectivity of encapsulated and unencapsulated catalysts

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UvA-DARE is a service provided by the library of the University of Amsterdam (https://dare.uva.nl)UvA-DARE (Digital Academic Repository)Supramolecular control of regioselectivity in the hydroformylation reactionSubstrate preorganization and second coordination sphere catalysisLinnebank, P.R.Publication date2021Link to publicationCitation for published version (APA):Linnebank, P. R. (2021). Supramolecular control of regioselectivity in the hydroformylationreaction: Substrate preorganization and second coordination sphere catalysis. [Thesis, fullyinternal, Universiteit van Amsterdam].General rightsIt is not permitted to download or to forward/distribute the text or part of it without the consent of the author(s)and/or copyright holder(s), other than for strictly personal, individual use, unless the work is under an opencontent license (like Creative Commons).Disclaimer/Complaints regulationsIf you believe that digital publication of certain material infringes any of your rights or (privacy) interests, pleaselet the Library know, stating your reasons. In case of a legitimate complaint, the Library will make the materialinaccessible and/or remove it from the website. Please Ask the Library: https://uba.uva.nl/en/contact, or a letterto: Library of the University of Amsterdam, Secretariat, Singel 425, 1012 WP Amsterdam, The Netherlands. Youwill be contacted as soon as possible.Download date:10 Mar 2023556688-L-os-LinnebankSupramolecular control of regioselectivity in the  hydroformylation reaction        Pim Linnebank 2021       Pim R. Linnebank        Supramolecular control of regioselectivity in the  hydroformylation reaction        Pim Linnebank 2021       Pim R. Linnebank        Supramolecular control of regioselectivity in the  hydroformylation reaction        Pim Linnebank 2021   Pim R. Linnebank        Supramolecular Control of Regioselectivity in the Hydroformylation reaction:Substrate Preorganization and SecondCoordination Sphere CatalysisInvitation   to the public defense of my thesis  Supramolecular Control of Regioselectivity in the  Hydroformylation reaction: Substrate Preorganization and Second Coordination Sphere Catalysis  On Wednesday the 31st of march at 11:00  Aula  Singel 411  Pim Linnebank pimlinnebank@gmail.com  Paranymphs:  Marie Brands mariebrands95@gmail.com  Tom Keijer tomkeijer@gmail.com             Invitationto the public defense of mythesisSupramolecular Control ofRegioselectivity in theHydroformylation reaction:Substrate Preorganizationand Second CoordinationSphere CatalysisOn Wednesday the 31st ofmarch at 11:00AulaSingel 411Pim Linnebankpimlinnebank@gmail.comParanymphs:Marie Brandsmariebrands95@gmail.comTom Keijertomkeijer@gmail.comSupramolecular Control of Regioselectivity in the Hydroformylation reaction: Substrate Preorganization and Second Coordination Sphere Catalysis ACADEMISCH PROEFSCHRIFT ter verkrijging van de graad van doctor aan de Universiteit van Amsterdam op gezag van de Rector Magnificus prof. dr. ir. K.I.J. Maex ten overstaan van een door het College voor Promoties ingestelde commissie, in het openbaar te verdedigenop woensdag 31 maart 2021, te 11.00 uur door Pim Rafael Linnebank geboren te Amsterdam     Promotiecommissie  Promotor:   prof. dr. J.N.H. Reek   Universiteit van Amsterdam Copromotor: dr. A.M. Kluwer InCatT B.V. Overige leden: prof. dr. B. de Bruin Universiteit van Amsterdam  prof. dr. G.J.M. Gruter Universiteit van Amsterdam  prof. dr. E.J. Meijer Universiteit van Amsterdam  dr. M.A. Fernández Ibáñez Universiteit van Amsterdam  prof. dr. S.R. Harutyunyan Rijksuniversiteit Groningen  prof. dr. M. Costas Universitat de Girona    Faculteit der Natuurwetenschappen, Wiskunde en Informatica Table of Contents  Chapter 1  Introduction: Supramolecular Approaches to Control      Activity and Selectivity in Hydroformylation Catalysis  3  Chapter 2 Unraveling the Origin of the Regioselectivity of a   45   Supramolecular Hydroformylation Catalyst   Chapter 3  Regioselective Hydroformylation of Internal and  69   Terminal Alkenes via Remote Supramolecular Control   Chapter 4  Regioselective Hydroformylation of ω-Unsaturated Acids  97  via Supramolecular Control Using a  1,3,-Benzenedicarboxamide Receptor Functionalized  Bidentate Ligand   Chapter 5  A Substrate Scope Driven Optimization of an Encapsulated  135  Hydroformylation Catalyst   Chapter 6  Substrate Descriptor Based Approach for the prediction  161   of the Regioselectivity of an Encapsulated       Hydroformylation Catalyst  Summary         179 Nederlandse samenvatting      187 List of publications       195 Dankwoord/Acknowlegements      197          

Supramolecular control of regioselectivity in the hydroformylation reaction:Substrate preorganization and second coordination sphere catalysis

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Supramolecular control of regioselectivity in the hydroformylation reaction:Substrate preorganization and second coordination sphere catalysis

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