Advances in Organometallic Chemistry and Catalysis

ARMANDO J. L. POMBEIRO is Full Professor at the Instituto Superior Técnico in Lisbon (Portugal), Full Member of the Academy of Sciences of Lisbon (in charge of various directive and representative positions) and President of the Portuguese Electro-chemical Society. His research group investigates the activation of small molecules with industrial, environmental or biological significance, including metal-mediated synthesis and catalysis (e.g., functionalization of alkanes under mild conditions), crystal engineering of coordination compounds, design and self-assembly of polynuclear and supramolecular structures, molecular electrochemistry and theoretical studies. He was Chairman of the 25th ICOMC and member of organizing/scientific committees of 40 international conferences or schools. He authored one book (plus three as editor), (co-)authored 600 research publications, 33 patents, and presented 90 invited lectures at international conferences. His work has received ca. 11,000 citations, h-index = 48 (ISI Web of Knowledge). Among his many honors, Dr. Pombeiro has been awarded the Madinabeitia-Lourenço Prize from the Spanish Royal Chemical Society.

“The book is written in good scientific English and should be easily understood by a graduate-level scientist who has some familiarity with the topics.”  (Applied Organometallic Chemistry, 1 May 2015)

• PREFACE xiCONTRIBUTORS xvPART I ACTIVATION AND FUNCTIONALIZATION OF CARBON SINGLE BONDS AND OF SMALLMOLECULES 11 Organometallic Complexes as Catalysts in Oxidation of C—H Compounds 3Georgiy B. Shul’pin2 Toward Functionalization of Alkanes Under Environmentally Benign Conditions 15Armando J. L. Pombeiro3 Self-assembled Multicopper Complexes and Coordination Polymers for Oxidation and Hydrocarboxylation of Alkanes 27Alexander M. Kirillov, Marina V. Kirillova, and Armando J. L. Pombeiro4 Activation of C—O and C—F Bonds by Pincer-iridium Complexes 39Jason Hackenberg, Karsten Krogh-Jespersen, and Alan S. Goldman5 Functionalization of sp2 and sp3 Carbon Centers Catalysed by Polyoxometalates and Metalloporphyrins 59M´ario M. Q. Sim˜oes, Isabel C. M. S. Santos, Maria Gra¸ca P. M. S. Neves, Ana M. V. Cavaleiro, and Jos´e A. S. Cavaleiro6 Quasi-borinium Cation Based on Cobalt Bis(dicarbollide): Its Lewis Acidity and C—H and C—X Bond Activation 73V. I. Bregadze, I. B. Sivaev, I. D. Kosenko, I. A. Lobanova, Z. A. Starikova, and I. A. Godovikov7 Transition-metal-promoted Functionalization of Carboranes 81Zaozao Qiu and Zuowei Xie8 Weak Interactions and M—H Bond Activation 97Elena Shubina, Natalia Belkova, Oleg Filippov, and Lina EpsteinPART II ORGANOMETALLIC SYNTHESIS AND CATALYSIS 1119 Complexes with Protic N-Heterocyclic Carbene (NR,NH-NHC) Ligands 113F. Ekkehardt Hahn10 Cyclopentadienyl-functionalized N-Heterocyclic Carbene Complexes of Iron and Nickel: Catalysts for Reductions 133Beatriz Royo11 Palladium-(acyclic diaminocarbene) Species as Alternative to Palladium-(nitrogen heterocyclic carbenes) in Cross-coupling Catalysis 145Vadim P. Boyarskiy, Konstantin V. Luzyanin, and Vadim Yu. Kukushkin12 Synthesis of Metallocenes Via Metathesis in Metal Coordination Spheres 157Antoni Pietrzykowski and W©©odzimierz Buchowicz13 Metal-mediated [2 + 3] Dipolar Cycloaddition to Substrates with CN Triple Bond: Recent Advances 171Konstantin V. Luzyanin and Maxim L. Kznetsov14 Coordination Chemistry of Oxazoline/Thiazoline-based P,N Ligands 185Shuanming Zhang, Roberto Pattacini, and Pierre Braunstein15 “Click” Copper Catalyzed Azide-alkyne Cycloaddition (CuAAC) in Aqueous Medium 199Joaqu´©¥n Garc´©¥a-A´lvarez and Jose´ Gimeno16 Organogold Catalysis: Homogeneous Gold-catalyzed Transformations for a Golden Jubilee 207Fabien Gagosz17 Vanadium(IV) Complexes Derived from Aromatic o-Hydroxyaldehydes and Tyrosine Derivatives: Catalytic Evaluation in Sulfoxidations 227Jo˜ao Costa Pessoa, Isabel Correia, and Pedro Ad˜ao18 Microwave-assisted Catalytic Oxidation of Alcohols to Carbonyl Compounds 233Yauhen Yu. Karabach, Maximilian N. Kopylovich, Kamran T. Mahmudov, and Armando J. L. Pombeiro19 Oxidation of Glycerol with Hydrogen Peroxide Catalyzed by Metal Complexes 247Dalmo Mandelli, Wagner A. Carvalho, Lidia S. Shul’pina, Alexander M. Kirillov, Marina V. Kirillova,Armando J. L. Pombeiro, and Georgiy B. Shul’pin20 Involvement of an Acetato Ligand in the Reductive Elimination Step of the Rhodium-catalyzed Methanol Carbonylation 259Duc Hanh Nguyen, Nicolas Lassauque, Thomas Davin, Laurent Maron, Carole Le Berre, Philippe Serp, and Philippe Kalck21 Half-sandwich Rhodium(III), Iridium(III), and Ruthenium(II) Complexes with Ancillary Pyrazole-based Ligands 269Claudio Pettinari, Riccardo Pettinari, Corrado Di Nicola, and Fabio Marchetti22 Carbon-scorpionate Complexes in Oxidation Catalysis 285Lu´©¥sa M. D. R. S. Martins and Armando J. L. Pombeiro23 Toward Chemoselective Bioconjugative Desulfitative Catalysis 295Lanny S. Liebeskind and Ethel C. Garnier-Amblard24 Sulfoxide Redox Chemistry with Molybdenum Catalysts 305Maria Jos´e Calhorda and Luis F. Veiros25 A New Family of Zirconium Complexes Anchored by Dianionic Cyclam-based Ligands: Syntheses,Structures, and Catalytic Applications 315Ana M. Martins, Rui F. Munh´a, Luis G. Alves, and Shanmuga Bharathi26 Metal-organo Multicatalysis: An Emerging Concept 325Alexandre F. Trindade, Jo˜ao N. Rosa, F´abio M. F. Santos, and Pedro M. P. GoisPART III ORGANOMETALLIC POLYMERIZATION CATALYSIS 34327 Coordinative Chain Transfer Polymerisations and Copolymerisations by Means of Rare EarthsOrganometallic Catalysts for the Synthesis of Tailor-made Polymers 345Marc Visseaux, Thomas Chenal, and Philippe Zinck28 Charge-neutral and Cationic Complexes of Large Alkaline Earths for Ring-opening Polymerizationand Fine Chemicals Catalysis 359Jean-Fran¸cois Carpentier, Bo Liu, and Yann SarazinPART IV ORGANOMETALLIC POLYMERS AND MATERIALS 37929 Organometallic Polymers 381Manuel Serrano-Ruiz, Franco Scalambra, and Antonio Romerosa30 From Serendipity to Porosity: Synthesis and Reactivity of Coordination Polymers Based on Copper Trinuclear Triangular Motifs 407Luciano Pandolfo31 Organometallic Nanoparticles 421Patricia Lara, Karine Philippot, Lise-Marie Lacroix, S´ebastien Lachaize, Nikos Liakakos, Katerina Soulantica, and Bruno Chaudret32 Organometallic Compounds in the Synthesis of New Materials: Old Ligands, New Tricks 437Piotr Sobota and ¨©ukasz John33 The Role of Organometallic Complexes in the Synthesis of Shaped Carbon Materials 445Neil J. Coville and Edward N. Nxumalo34 Metal Catalysis in Fullerene Chemistry 459Salvatore Filippone, Enrique E. Maroto, A´ngel Mart´©¥n-Domenech, and Nazario Mart´©¥n35 Organometallic Complexes of Sumanene 473Toru Amaya and Toshikazu Hirao36 Advances in Luminescent Tetracoordinate Organoboron Compounds 485D. Suresh and Pedro T. Gomes37 Mechanochemistry: A Tool in the Synthesis of Catalysts, Metallodrugs, and Metallopharmaceuticals 493Vˆania Andr´e, Clara S. B. Gomes, and M. Teresa DuartePART V ORGANOMETALLIC CHEMISTRY AND SUSTAINABLE ENERGY 50138 Organometallic Complexes for Dye-sensitized Solar Cells (DSSC) 503Delele W. Ayele, Wei-Nein Su, John Rick, Hung-Ming Chen, Chun-Jern Pan, Nibret G. Akalework, and Bing-Joe Hwang39 Synthetic Photosynthesis for the Conversion of Large Volumes of Carbon Dioxide into Energy-Rich Molecules: Saving Fossil Fuels by Recycling Carbon 513Michele Aresta and Angela Dibenedetto40 Ionic Liquids for Hydrogen Storage: Opportunities for Organometallic Chemistry 529Martin H. G. Prechtl and Sebastian SahlerPART VI BIOORGANOMETALLIC CHEMISTRY 54341 Metal Carbonyls for CO-based Therapies: Challenges and Successes 545Carlos C. Rom˜ao and Helena L. A. Vieira42 The Ferrocifen Family as Potent and Selective Antitumor Compounds: Mechanisms of Action 563G´erard Jaouen and Siden Top43 On the Track to Cancer Therapy: Paving New Ways With Ruthenium Organometallics 581Tˆania S. Morais and M. Helena Garcia44 Organometallic Chemistry of Rhenium and Technetium Fueled by Biomedical Applications 589Ant´onio Paulo, Goreti Ribeiro Morais, and Isabel Santos45 Metal-based Indolobenzazepines and Indoloquinolines: From Moderate cdk Inhibitors to Potential Antitumor Drugs 605Michael F. Primik, Lukas K. Filak, and Vladimir B. Arion46 Metal-based Chelates and Nanosystems as MRI Contrast Agents 619Sara Figueiredo and Carlos F. G. C. GeraldesPART VII ORGANOMETALLIC ELECTROCHEMISTRY 63147 Electrochemistry and Supramolecular Interactions of “Ferrocifen” Anticancer Drugs with Cyclodextrins and Lipid Bilayers: An Electrochemical Overview 633Olivier Buriez, Eric Labb´e, and Christian Amatore48 Electrochemistry of Fischer Aminocarbene Complexes: Effects of Structure on Redox Properties, Electron Distribution, and Reaction Mechanisms 653Ji¢§r´©¥ Ludv´©¥k and Irena Hoskovcov´a49 Electron Transfer-induced Coordination Changes in Organometallic Complexes with Non-innocent Hemilabile Ligands 667Wolfgang Kaim, Martina Bubrin, and Ralph H¨ubner50 Redox Potential–Structure Relationships and Parameterization in Characterization and Identification of Organometallic Compounds 677M. F´atima C. Guedes da Silva and Armando J. L. Pombeiro51 Endohedral Metallofullerenes Today: More and More Versatile Ships in Multiform Bottles—Electrochemistry of X-Ray Characterized Monometallofullerenes 691Fabrizia Fabrizi de Biani and Piero ZanelloPOSTSCRIPT: A SHORT HISTORY OF THE ICOMC CONFERENCES 703Ekkehardt HahnINDEX 707