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The Potential of Hydroaminomethylation : Directing the Cascade The potential of hydroaminomethylation : directing the cascade Citation for published version (APA): Hamers, B. (2009). The potential of hydroaminomethylation : directing the cascade. Technische Universiteit Eindhoven. https://doi.org/10.6100/IR653939 DOI: 10.6100/IR653939 Document status and date: Published: 01/01/2009 Document Version: Publisher’s PDF, also known as Version of Record (includes final page, issue and volume numbers) Please check the document version of this publication: • A submitted manuscript is the version of the article upon submission and before peer-review. There can be important differences between the submitted version and the official published version of record. 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If the publication is distributed under the terms of Article 25fa of the Dutch Copyright Act, indicated by the “Taverne” license above, please follow below link for the End User Agreement: www.tue.nl/taverne Take down policy If you believe that this document breaches copyright please contact us at: [email protected] providing details and we will investigate your claim. Download date: 23. Sep. 2021 The Potential of Hydroaminomethylation Directing the Cascade This research has been financially supported by the NWO-ACTS Aspect program (ASPECT 053.62.009). Coverdesign by Anique Pfennings Printed at Wöhrmann Print Service, Zutphen A catalogue record is available from the Eindhoven University of Technology Library The Potential of Hydroaminomethylation – Directing the Cascade / by Bart Hamers – Eindhoven : Technische Universiteit Eindhoven, 2009. Proefschrift. – ISBN 978-90-8570-411-9 Subject headings: rhodium-catalysed hydroaminomethylation / phosphorus ligands / coordination chemistry / solvent influences / selectivity / catalyst recycling Copyright © 2009, Bart Hamers The Potential of Hydroaminomethylation Directing the Cascade PROEFSCHRIFT ter verkrijging van de graad van doctor aan de Technische Universiteit Eindhoven, op gezag van de rector magnificus, prof.dr.ir. C.J. van Duijn, voor een commissie aangewezen door het College voor Promoties in het openbaar te verdedigen op donderdag 22 oktober 2009 om 16.00 uur door Bart Hamers geboren te Born Dit proefschrift is goedgekeurd door de promotor: prof.dr. D. Vogt Copromotor: dr. C. Müller ‘Don’t ask yourself if it’s a long road. Ask yourself if it’s a good journey.’ Sidney Poitier Table of Contents Chapter 1 Hydroaminomethylation, a cascade reaction with potential 1 1.1 Relevance and preparation of amines 2 1.2 General aspects of hydroaminomethylation reactions 4 1.2.1 Hydroformylation 5 1.2.2 Reductive amination 9 1.3 A concise review on hydroaminomethylation 12 1.4 Aim and scope of this research 17 1.5 References 19 Chapter 2 Hydroaminomethylation of n-alkenes in a biphasic ionic liquid system 23 2.1 Introduction 24 2.1.1 Ionic Liquids 24 2.1.2 Catalyst recyling 25 2.2 Biphasic catalysis and catalyst recycling 26 2.3 Product distribution in time 31 2.4 Influence of the catalyst precursor 34 2.5 Solvent effect in the hydroaminomethylation 36 2.6 Turnover frequencies 39 2.7 Conclusions 40 2.8 Experimental section 41 2.9 References 43 Chapter 3 Fast and selective hydroaminomethylation of n-alkenes using xanthene-based amino- functionalised ligands 45 3.1 Introduction 46 3.2 Ligand synthesis 48 3.3 Catalysis 51 3.4 Solvent mixture composition 56 3.5 Conclusions 61 3.6 Experimental section 61 3.7 References 67 Chapter 4 Hydroaminomethylation of internal alkenes using xanthene-based amino-functionalised ligands 69 4.1 Introduction 70 4.2 Synthesis of substituents and ligands 74 4.3 Catalysis 77 4.3.1 Xanthene with rigid, bulky substituents 77 4.3.2 Synthesis gas ratio 78 Table of Contents 4.3.3 Effect of catalyst preformation 80 4.3.4 Influence of reaction temperature 82 4.3.5 Solvent influence 83 4.3.6 Addition of a monodentate phosphorus ligand 85 4.4 Conclusions 88 4.5 Experimental section 89 4.6 References 92 Chapter 5 Coordination chemistry of xanthene-based amino-functionalised ligands 95 5.1 Introduction 96 5.2 Coordination chemistry 99 5.2.1 Rhodium 99 5.2.2 Platinum 105 5.2.3 Selenium 107 5.2.4 High pressure NMR and IR experiments 108 5.3 Conclusions 110 5.4 Experimental section 111 5.5 References 115 Chapter 6 Future perspectives on hydroaminomethylation 117 6.1 Introduction 118 6.2 Ammonia in the hydroaminomethylation reaction 120 6.3 Protection by carbon dioxide 122 6.4 Primary amines by sequential HAM/deprotection 125 6.5 Conclusions 127 6.6 Experimental section 128 6.7 References 129 Summary 133 Samenvatting 136 Curriculum Vitae 139 List of Publications 140 Dankwoord 141 ii 11 Hydroaminomethylation, a cascade reaction with potential Amines are important building blocks in the bulk chemical as well as in the pharmaceutical industry. Classical syntheses of amines often lead to large amounts of waste, mainly inorganic salts. One of the most promising new reactions for the production of amines in terms of atom- efficiency, activity, selectivity, and applicability is the hydroaminomethylation of alkenes in which water is the only side product. Especially the possibility to synthesise primary amines atom- efficiently from cheap alkene feedstocks and ammonia by hydroaminomethylation makes this an interesting reaction from an industrial point of view. Although the hydroaminomethylation has been discovered already in 1949, intensive research with respect to this reaction has been performed during the last 15 years. A review of the most interesting aspects of this reaction will be presented in this chapter. Part of this work will be submitted for publication: B. Hamers, C. Müller, D. Vogt, manuscript in preparation Chapter 1 1.1 Relevance and preparation of amines Besides the relevance of amines in the human body in the form of DNA and amino acids, amines are also important in everyday life for a broad range of building blocks and end products such as polymers, lubricating oils, waterproofing agents in textiles, detergents, dyes, pesticides, pharmaceuticals, and even stabilisers for explosives. Although the production scale of polymer and pharmaceutical products is completely different, illustrative examples showing the relevance of amines can be found for both product classes. In the class of polymer products, 1,6-diaminohexane, 1,4-diaminobutane, ε-caprolactam, and 11-aminoundecanoic acid are examples of important amine building blocks for the synthesis of the polyamides Nylon-6,6, Nylon-4,6, Nylon-6, and Nylon-11, respectively. Most Nylon types are synthesised via a polycondensation reaction of the amine functionality with a carboxylic acid functional group or via a ring-opening polymerisation. The stiffness and high melting points of polyamides are important properties, which are mostly caused by intermolecular hydrogen bonding. Nylon finds its applications in many important products such as ballistic vests, airbags, tights and other textiles, dental floss, fishing lines, chords of musical instruments, insulating coatings of cables et cetera. Many pharmaceutical products or active pharmaceutical ingredients contain amino groups. Methylphenidate (Fig. 1.1), for example, is derived from amphetamine and is the active ingredient in pharmaceuticals such as Ritalin and Concerta, which are the most commonly prescribed psychostimulants in the treatment of attention-deficit hyperactivity disorder (ADHD), sleeping disorders and narcolepsy.[1,2] This drug acts by increasing levels of norepinephrine, serotonin and dopamine in the brain, inducing euphoria. Another well- known pharmaceutical is Imipramine (Fig. 1.1) which is the first drug of the class of tricyclic antidepressants to be developed in the late 1950s. [3] These tricyclic antidepressants have mainly been used in the treatment of major depression and insomnia, although alternatives, also including amine functionalities, have been developed during the last decade. [4] Consequently, the preparation of amines is an important issue in synthetic chemistry. [5,6] Many different organic reactions for the synthesis of amines such as nucleophilic substitution of haloalkanes, Buchwald-Hartwig reaction of amines and aryl halides, reduction of nitriles, amides, or nitro compounds, and Gabriel synthesis are known. The industrial process for the production of amines usually produces large amounts of waste, mainly inorganic salts, together with the desired amine product. In many cases, the amount of waste produced is even much larger than the amount of product. Since sustainability is an important issue in chemical 2 Hydroaminomethylation, a cascade reaction with potential
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