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UNIVERSITY of CALIFORNIA, SAN DIEGO Metal Complexes Of UNIVERSITY OF CALIFORNIA, SAN DIEGO Metal Complexes of Tripodal N-Heterocyclic Carbene Ligands: Synthesis, Structure, Bonding, and Reactivity A dissertation submitted in partial satisfaction of the requirements for the degree Doctor of Philosophy in Chemistry by Xile Hu Committee in charge: Professor Karsten Meyer, Chair Professor David N. Hendrickson Professor Melvin Okamura Professor Charles L. Perrin Professor William C. Trogler 2004 Copyrights© Xile Hu, 2004 All rights reserved. The dissertation of Xile Hu is approved, and it is acceptable in quality and form for publication on microfilm. Chair University of California, San Diego 2004 iii Dedicated with love and appreciation to my mother Xiulan Lin and my father Fusheng Hu iv Habe nun, ach! Philosophie, I've studied now Philosophy Juristerei und Medizin, And Jurisprudence, Medicine, Und leider auch Theologie, And even, alas! Theology Durchaus studiert, mit heissem Bemuehn. All through and through with ardour keen! Da steh' ich nun, ich armer Tor, Here now I stand, poor fool, and see Und bin so klug als wie zuvor! I'm just as wise as formerly. Heisse Magister, heisse Doktor gar, Am called a Master, even Doctor too, Und ziehe schon an die zehen Jahr' And now I've nearly ten years through Herauf, herab und quer und krumm Pulled my students by their noses to and fro Meine Schueler an der Nase herum -- And up and down, across, about, Und sehe, dass wir nichts wissen koennen! And see there's nothing we can know! ----Goethe "Faust" v TABLE OF CONTENTS Signature Page...............................................................................................................iii Dedication......................................................................................................................iv Epigraph .........................................................................................................................v Table of Contents ..........................................................................................................vi List of Symbols and Abbreviations ...............................................................................xi List of Figures..............................................................................................................xvi List of Schemes .........................................................................................................xxiii List of Tables..............................................................................................................xxv Acknowledgement...................................................................................................xxviii Vita .............................................................................................................................xxx Publications ...............................................................................................................xxxi Abstract of the Dissertation.....................................................................................xxxiii Chapter 1. Introduction to Carbenes and N-Heterocyclic Carbenes...............................1 1.1. Carbenes ..............................................................................................................2 1.2. N-Heterocyclic Carbenes.....................................................................................4 1.3. Molecular and Electronic Structure of N-Heterocyclic Carbenes.......................5 1.4. Reactivity and Ligand Properties of N-Heterocyclic Carbenes ..........................7 1.5. N-Heterocyclic Carbenes in Homogeneous Catalysis.........................................8 1.6. Bi- and Polydentate N-Heterocyclic Carbene Ligands .......................................9 1.7. Objectives..........................................................................................................10 1.8. Acknowledgement.............................................................................................13 vi 1.9. References .........................................................................................................14 Chapter 2. A Carbon-Anchored Tripodal N-Heterocyclic Carbene Ligand System and Its Coordination to Group 11 Metal Ions……………………………………………..20 2.1. Introduction .......................................................................................................21 2.2. Results and Discussion......................................................................................22 R 2.2.1. Synthetic protocol for the imidazolium precursors [H3TIME ]X3 (R = alkyl, X = Br, PF6)..........................................................................................................22 2.2.2. The TIMEMe ligand and its coordination to silver(I)..................................23 2.2.3. Synthesis and characterization of copper(I) and gold(I) complexes of TIMEMe.................................................................................................................27 2.2.4 The TIMEt-Bu ligand and its coordination to copper(I)................................34 2.3. Conclusion.........................................................................................................40 2.4. Experimental Section.........................................................................................41 2.5. Acknowledgement.............................................................................................49 2.6. Appendix ...........................................................................................................50 2.7. References .........................................................................................................58 Chapter 3. A Nitrogen-Anchored Tripodal N-Heterocyclic Carbene Ligand System and Its Coordination to Copper……………………………………………………….60 3.1. Introduction .......................................................................................................61 3.2. Results and Discussion......................................................................................62 3.2.1 Ligand synthesis ..........................................................................................62 Me 3.2.2. Synthesis and characterization of trinuclear [(TIMEN )2Cu3](PF6)3 .......63 3.2.3. Synthesis and characterization of mononuclear [(TIMENR)Cu]+. .............66 vii Bz 3.2.4. Synthesis and characterization of [(TIMEN )Cu](OTf)2..........................72 3.2.4. Reactivity survey of [(TIMEN)Cu]+...........................................................75 3.3. Conclusion.........................................................................................................76 3.4. Experimental Section.........................................................................................77 3.5. Acknowledgement.............................................................................................85 3.6. Appendix ...........................................................................................................87 3.7. References .........................................................................................................91 Chapter 4. Synthesis and Characterization of Electron-Rich Nickel Tris(Carbene) Complexes…………………………………………………………………………….93 4.1. Introduction .......................................................................................................94 4.2. Results and Discussion......................................................................................95 4.2.1. Synthesis and characterization of the nickel(0) complex [Ni(TIMENt-Bu)]95 4.2.1. Synthesis and characterization of the nickel(I) complex [Ni(TIMENt-Bu)]+ ..............................................................................................................................99 4.3. Conclusion.......................................................................................................101 4.4. Experimental Section.......................................................................................102 4.5. Acknowledgement...........................................................................................104 4.6. Appendix .........................................................................................................105 4.7. References .......................................................................................................108 Chapter 5. Cobalt Tris(Carbene) Complexes: Small Molecule Binding, Dioxygen Activation, and Imido Transfer……………………………………………………...110 5.1. Introduction .....................................................................................................111 5.2. Results and Discussion....................................................................................114 viii 5.2.1. Synthesis of complex [(TIMENxyl)Co]Cl (1a) .........................................114 5.2.2. Synthesis and structure of complex [(TIMENxyl)Co(CO)]Cl (2) .............116 5.2.3. Synthesis and structure of complexes [(TIMENxyl)Co(Cl)]Cl (3) and xyl [(TIMEN )Co(CH3CN)](BPh4)2 (4) .................................................................118 5.2.4. Electronic absorption spectra and magnetic properties of complexes 1a, 2-4 ............................................................................................................................122 5.2.5. Synthesis and structure of the cobalt dioxygen complex [(TIMENxyl)Co- (O2)]BPh4 (5)......................................................................................................125 xyl + 5.2.6. DFT study on complex [(TIMEN )Co(O2)]
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