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Investigations Into the Synthesis and Properties of Atropisomeric N–Heterocyclic Carbenes

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Investigations Into the Synthesis and Properties of Atropisomeric N–Heterocyclic Carbenes Investigations Into the Synthesis and Properties of Atropisomeric N–Heterocyclic Carbenes A Thesis Submitted for the Degree of Doctor of Philosophy in Chemistry at the University of New South Wales School of Chemistry By MILENA L. CZYZ MARCH 2012 THE UNIVERSITY OF NEW SOUTH WALES Thesis/Dissertation Sheet Surname or Family name: CZYZ First name: MILENA Other name/s: LIDIA Abbreviation for degree as given in the University calendar: PhD School: CHEMISTRY Faculty: SCIENCES Title: Investigations into the Synthesis and Properties of Atropisomeric N-Heterocyclic Carbenes Abstract 350 words maximum: This thesis describes the development of chiral N–heterocyclic carbenes (NHCs) substituted with N–binaphthyl groups. Their catalytic utility is examined in homogenous organometallic reactions and organocatalysis. Chapter 1 provides an introduction to asymmetric catalysis. The use of chiral phosphines is described, followed by the properties, design and applications of chiral NHCs. Chapter 2 discusses the synthesis of NHC precursors with biaryl substituents and chirality at the 4- and 5-positions of the imidazole. Two pathways utilising Pd–catalysed reactions were examined, however preparation of the target compound proved challenging. This resulted in the development of a new design, where chirality is moved from the backbone to the N–substituents. This approach required access to atropisomeric binapthyl amines as the key starting materials. Chapter 3 describes the synthesis of atropisomeric binaphthyl amines using the asymmetric Pinhey–Barton chemistry and the BINOL approach. Chiral oxazoline ligands were applied to the Pinhey–Barton reaction for the first time, and their interactions with aryllead triacetates investigated using 1H NMR spectroscopy. The preparation of the required binaphthyl amine was achieved by selective functionalisation of (M)–BINOL. Chapter 4 describes the transformation of the atropisomeric binaphthyl amine into imidazolium salt disubstituted with chiral binaphthyls. Complexes with transition metals were synthesised and their electronic properties and conformational stabilities examined using spectroscopic techniques. In catalysis, the new Rh(I)–NHC complexes showed good reactivities in the asymmetric hydrosilylation and hydrogen transfer reactions, however only poor enantioselecties were observed. Efforts to improve reactivity did not result in a corresponding increase in enantioselectivity, highlighting the need to minimise exocyclic C–N bond rotation. Expansion of the family of atropisomeric NHC precursors to include 1,2,4–triazolium and thiazolium salts and their application in organocatalysis is described in Chapter 5. The fluxionality of the heteroazolium salts was examined using 1H NMR spectroscopy. They showed interesting reactivities in the Stetter and Baylis–Hillman reactions, giving an insight into the effect of the steric properties of the NHC on chemoselectivity. Chapter 6 provides a summary of the work described in this thesis and suggests future developments. Full experimental procedures are included in Chapter 7. Declaration relating to disposition of project thesis/dissertation I hereby grant to the University of New South Wales or its agents the right to archive and to make available my thesis or dissertation in whole or in part in the University libraries in all forms of media, now or here after known, subject to the provisions of the Copyright Act 1968. I retain all property rights, such as patent rights. I also retain the right to use in future works (such as articles or books) all or part of this thesis or dissertation. I also authorise University Microfilms to use the 350 word abstract of my thesis in Dissertation Abstracts International (this is applicable to doctoral theses only). ……………………… ……………………………………..……………… ……….……………………...…….… Signature Witness Date The University recognises that there may be exceptional circumstances requiring restrictions on copying or conditions on use. Requests for restriction for a period of up to 2 years must be made in writing. Requests for a longer period of restriction may be considered in exceptional circumstances and require the approval of the Dean of Graduate Research. FOR OFFICE USE ONLY Date of completion of requirements for Award: i ORIGINALITY STATEMENT ‘I hereby declare that this submission is my own work and to the best of my knowledge it contains no materials previously published or written by another person, or substantial proportions of material which have been accepted for the award of any other degree or diploma at UNSW or any other educational institution, except where due acknowledgement is made in the thesis. Any contribution made to the research by others, with whom I have worked at UNSW or elsewhere, is explicitly acknowledged in the thesis. I also declare that the intellectual content of this thesis is the product of my own work, except to the extent that assistance from others in the project's design and conception or in style, presentation and linguistic expression is acknowledged.’ Signed …………………………………………….............. Date …………………………………………….............. ii COPYRIGHT STATEMENT ‘I hereby grant the University of New South Wales or its agents the right to archive and to make available my thesis or dissertation in whole or part in the University libraries in all forms of media, now or here after known, subject to the provisions of the Copyright Act 1968. I retain all proprietary rights, such as patent rights. I also retain the right to use in future works (such as articles or books) all or part of this thesis or dissertation. I also authorise University Microfilms to use the 350 word abstract of my thesis in Dissertation Abstract International (this is applicable to doctoral theses only). I have either used no substantial portions of copyright material in my thesis or I have obtained permission to use copyright material; where permission has not been granted I have applied/will apply for a partial restriction of the digital copy of my thesis or dissertation.' Signed ……………………………………………........................... Date ……………………………………………........................... AUTHENTICITY STATEMENT ‘I certify that the Library deposit digital copy is a direct equivalent of the final officially approved version of my thesis. No emendation of content has occurred and if there are any minor variations in formatting, they are the result of the conversion to digital format.’ Signed ……………………………………………........................... Date ……………………………………………........................... iii Acknowledgements First of all, I would like to thank my supervisor, A/Prof Jonathan Morris, for his guidance and support throughout my PhD. I appreciate all the time you have spent discussing my project, answering my questions, challenging me and coming up with new ideas. I am especially grateful for your assistance in the last 6 months. I would like to extend this thank you to my co-supervisor, A/Prof Marcus Cole, for his helpful suggestions, insights and a slightly different perspectives on this project, and for the X-ray crystal structures. I am very grateful that you found time to read and correct drafts of this thesis. Thanks to the entire Morris Group, those back in Adelaide (Jason, Erin and Scott) and here at UNSW. In particular, I would like to acknowledge Dr Jason Brusnahan for spending a lot of time helping me out when I first joined the group. Special thank you to Belinda, who's been such a wonderful friend, housemate and a travel companion. Thank you Hamish for running HRMS samples, lunchtime "chats" and (I know I will deeply regret saying this) just being yourself. Justin, for facing my grumpiness in the lab right next to me with admirable stoicism; Joana, for all the lollies and ganging up with me against Hamish; and Veronica for coffee breaks and sharing my enjoyment of geeky jokes that nobody else appreciated. Thank you to the Cole Group, especially Sam and Matt, for helping with transition to UNSW and the great tradition of Friday Night Drinks. Thank you Sam for being a great housemate, a gym buddy and for always letting me vent after a particularly vexing day in the lab. Thank you for organising the "Milena's Submission Partay!" Thank you to all the technical support officers in Adelaide and Sydney: especially Dr Donald Thomas, Dr Douglas Lawes and Adelle Amoore (UNSW NMR facility) and Lewis Adler and Dr Leanne Stephenson (BMSF). Thank you Adelaide University for the PhD scholarship and UNSW for the APA. Thank you Ben for your understanding over the past two years. I know it hasn't been easy, but you never complained and were always considerate and supportive. Last, but not least, I would like to thank all my family for their love and support. I'm always looking forward to flying back home, where I rest and recharge my batteries, and it's a great comfort to know that I can always do that. I am extremely grateful to my Mum for having that insane determination over 10 years ago, because, otherwise, I would definitely not be here now. iv Abstract This thesis describes the development of chiral N–heterocyclic carbenes (NHCs) substituted with N–binaphthyl groups. Their catalytic utility is examined in homogenous organometallic reactions and organocatalysis. Chapter 1 provides an introduction to asymmetric catalysis with a discussion of how chiral phosphines are used, followed by the properties, design and applications of chiral NHCs. Chapter 2 discusses the synthesis of NHC precursors with biaryl substituents and chirality at the 4– and 5–positions of the imidazole.
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