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2015TOU30155.Pdf . . 2 . . . . . . . 2 . . . . . Acknowledgement I would like to thank the jury members Dr. Alessandra Quadrelli and Dr. Ally Aukoloo for accepting to act as Reviewers for my thesis, Prof. Parisa Mehrkhodavandi and Prof. Fabien Delpech for accepting to examine my Ph.D study. I would like to give my special appreciation to my supervisor Dr. Sylviane Sabo-Etienne, first for accepting me in the team and second for her endless guidance, patience, support and motivation, and additionally for her enthusiastic interest in new results. I also would like to thank for her kindness and mother-like attitude beyond as a supervisor. I really like the Christmas parties organized by her, and the gifts given by her after any long time conference she took part in. I also would like to thank my co-supervisor Dr. Sébastien Bontemps for his guidance and vast knowledge during priceless scientific discussions, support and encouragement during my Ph.D study. I am very happy to have a chance to work with him, because his American style humor always makes the Lab work lively and easy. I would like to thank Dr. Gilles Alcaraz and Dr. Mary Grellier for their kind help in the lab as well as the help during daily life. I benefited a lot from them, not only the knowledge in chemistry, but also the attitude to work. I also would like to thank Dr. Laure Vendier, Dr. Jean-Claude Daran and Dr. Rémy Brousses for the X-ray data collection; Dr. Yannick Coppel and Dr. Christian Bijani for NMR experiments and for their valuable scientific discussions; Dr. Francis Lacassin and Dr. David Paryl for NMR training; Dr. Alain Moreau for elemental analyses; and all the others who indeed help me to finish my Ph.D smoothly. My special thanks to my lab-mate Katie Smart, who never stops helping and encouraging me; to my friend Nuria Romero, who is the “lucky girl” of my reactions; to my friends Weili Wang, Jin Wang, Gunnar Werncke and Uta Baddack, Emmanuel Puig and Tugce Ayvali, who always make me feel at home in France and also for their endless encouragement and motivation throughout my Ph.D studies. It would be impossible to finish this challenging road without these valuable people. I appreciate their presence, friendship and amusement. All current and former Equipe O members, Emmanuelle Mothes-Martin, Chris Wallis, Gaetan Benac-Lestrille, Audrey Cassen, Charly Faradji, Alain Eschlimann, Marion Beguerie, Carlos Pinheiro, Yannick Escudié and Alexandre Mau, together with the visitors we were lucky enough to host throughout the world, Cynthia Cuevas Chavez, Julio Zamora Moreno, Tatsuro Annaka, Vicky Corona, Prof. Alan Goldman and Prof. Christian Limberg for their scientific discussions and also good friendship. Many thanks also to the colleagues from other groups of LCC, Marlene, Mahmoud, Yohan, Si, Emilie, Kais, Lucas, Quentin, Chen, Yin, Zhong, Mirko, Jérémy, Pascal, Roberto and so on for having amusement and pleasant moments in the last three years. Thanks to all CNRS employees for their smiling faces every day and endless help. China Scholarship Council (CSC) and ANR (Programme blanc “IRONHYC” ANR-12) are also acknowledged for financial support. The last but not the least, my special appreciation and great thankfulness are dedicated to my mum Tingyun, my dad Tieshan, my brother Zhenghua and my girlfriend Yandi for their love, patience, unconditional support and motivation. Contents List of Abbreviations General introduction………………………………………………………….……….1 Chapter 1 Bibliography………………………………………………………………………………………………5 Chapter 2 Synthesis and characterization of a new family of iron complexes………..….43 Chapter 3 Iron-catalyzed reductive functionalization of CO2…………………………..…………81 Chapter 4 General conclusion……………………………………………………………….…………………107 Chapter 5 Experimental sections…………………………………………………….………………………113 Appendices Appendix 1………………………………………………………………………………………………137 Appendix 2………………………………………………………………………………………………171 References………………………………………………………………………………181 Résumé Français List of abbreviations Acac acetylacetone Ar aromatic atm atmosphere BPPF 1’1-bis(diphenylphosphino)ferrocene COD cyclooctadiene COT cyclooctatriene DBU 1,8-diazabicyclo[5.4.0]-undec-7-ene dcpe 1,2-bis(cyclohexylphophino)ethane depe 1,2-bis(diethylphosphino)ethane DFT density functional theory diphos 1,2-bis(phenylphosphino)ethane dipp diisopropylphenyl DMF dimethylformamide dmpe 1,2-bis(dimethylphosphino)ethane dppe 1,2-bis(phenylphosphino)ethane EA elemental analysis Et2O diethyl ether Et ethyl EtNCS isothiocyanate eq. equivalent GPE glycidylphenylether HBpin pinacolborane HBcat catecholborane HS high spin HSPhSH 1,2-benzenedithiol HRMS High Resolution Mass Spectrometry iPr isopropyl LiHBEt3 Lithium triethylborohydride LS low spin MAO methylaluminoxane Me methyl MeCy methylcyclohexane MD’M methyl-bis(trimethylsilyloxy)silicon MMAO methylaluminoxane n ( Bu)4NI alkylammonium iodide NP (2-picolyl)diphenylphosphine NPN bis(2-picoly)phenylphosphine NTs N-tosyl OTf trifluoromethanesulfonate PDI bis(imino)prydine Ph phenyl PPh3 triphenylphosphine CH2Cy PhBP 3 tris(methylcyclohexylphosphino)phenylborate PO propyloxide PP3 tris(2-(diphenylphosphino)phenyl)phosphine [PPN]Cl bis(triphenylphosphino)iminium chloride THF tetrahydrofuran TON turnover number tBu tertiary butyl TBAB tetrabutylammonium TBDMS tert-butyldimethylsilyl TIPS triisopropylsilyl TMDS 1,1,4,4-tetramethyldisiloxane TMS trimethylsilyl [Tptm]H tris(2-pyridylthio)methane Xs excess 9-BBN 9-borabicyclo[3.3.1]nonane General introduction 1 2 General introduction Nowadays, the consumption of global energy has increased tremendously because of a growing world population and intensified industrialization. In this context, the development of energy saving and new energy producing processes affords the most important solution to meet the energy needs in the long term, and catalysis is one of the pivotal technologies. However, the dominant catalysts are based on precious metals, such as Ru, Rh, or Pd, for both academic and industrial applications. Concerning price and sustainability of the catalysts, iron thus appears to be a metal of choice because it is inexpensive, abundant and rather non-toxic. In this context, we focused on iron chemistry with two approaches. On one hand, the field of metal complexes bearing non-innocent ligands has attracted an increasing interest in the coordination chemistry community due to their potential catalytic properties. Substrates can be activated by both the metal center and the ligand allowing catalysis without changing the oxidation state of the metal center. On another hand, the field of CO2 transformation is also very attractive to benefit from this abundant molecule as a C1 source to replace fossil resources. However, its high thermodynamic stability is a challenge for its functionalization under mild conditions. In the last decade, CO2 has been transformed into HCOOH, CO, CH3OH, CH2O and CH4. By adding an amine to a mediated-reduction of CO2, the access to formamides and methylamines has been achieved. These processes pave the way to multicomponent transformations of CO2 to generate more complex and valuable molecules, but the scope of CO2 functionalization is still restricted to the formation of C-N bonds. Therefore, the first iron-based catalytic system was investigated for the transformation of CO2 into a large variety of compounds under mild conditions. The study “Coordination chemistry and catalysis at iron: from non-innocent ligands to CO2 transformation” was performed at the “Laboratoire de Chimie de Coordination du CNRS” in Toulouse, France, in the team “Architecture Organométallique et Catalyse” under the supervision of Sylviane Sabo-Etienne and Sébastien Bontemps. The dissertation is composed of five chapters. The first chapter is a bibliographic study concerning the chemistry of iron complexes involved in the two domains we selected: the combination of iron with non-innocent ligands leading to highly active catalysts, and the use of iron complexes for CO2 transformations, involving stoichiometric and catalytic activation of CO2. 3 In chapter 2, we have selected phosphine ligands bearing picolyl fragments which could favor a non-innocent behavior. By a careful control of the experimental conditions, a family of mono- and dimeric iron complexes has been isolated and the non-innocent behavior of the ligand has been observed. The combination of several techniques: X-ray diffraction, NMR (in solution and in the solid state), EPR, Mössbauer and infrared spectroscopy allows to characterize both diamagnetic and paramagnetic complexes. In chapter 3, the iron-catalyzed CO2 reductive functionalization is presented. A one-pot two-step strategy has been implemented under mild conditions. Our efforts to optimize the first iron- catalyzed CO2 reduction step to afford selectively a bis(boryl)acetal compound will be detailed. This intermediate has then been used as a reactive and versatile source of methylene in functionalization reactions, leading to a large scope of value-added organic compounds. In chapter 4, general remarks, conclusions and perspectives of the present work are described. Chapter 5 is dedicated to the experimental part of this manuscript. 4 Chapter 1 5 6 Chapter 1 Bibliography 1. Introduction .................................................................................................................................
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