Organometallic Polymers a
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“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)
Table of Contents
PREFACE xi
CONTRIBUTORS xv
PART I ACTIVATION AND FUNCTIONALIZATION OF CARBON SINGLE BONDS AND OF SMALL
MOLECULES 1
1 Organometallic Complexes as Catalysts in Oxidation of C—H Compounds 3
Georgiy B. Shul’pin
2 Toward Functionalization of Alkanes Under Environmentally Benign Conditions 15
Armando J. L. Pombeiro
3 Self-assembled Multicopper Complexes and Coordination Polymers for Oxidation and Hydrocarboxylation of Alkanes 27
Alexander M. Kirillov, Marina V. Kirillova, and Armando J. L. Pombeiro
4 Activation of C—O and C—F Bonds by Pincer-iridium Complexes 39
Jason Hackenberg, Karsten Krogh-Jespersen, and Alan S. Goldman
5 Functionalization of sp2 and sp3 Carbon Centers Catalysed by Polyoxometalates and Metalloporphyrins 59
M´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. Cavaleiro
6 Quasi-borinium Cation Based on Cobalt Bis(dicarbollide): Its Lewis Acidity and C—H and C—X Bond Activation 73
V. I. Bregadze, I. B. Sivaev, I. D. Kosenko, I. A. Lobanova, Z. A. Starikova, and I. A. Godovikov
7 Transition-metal-promoted Functionalization of Carboranes 81
Zaozao Qiu and Zuowei Xie
8 Weak Interactions and M—H Bond Activation 97
Elena Shubina, Natalia Belkova, Oleg Filippov, and Lina Epstein
PART II ORGANOMETALLIC SYNTHESIS AND CATALYSIS 111
9 Complexes with Protic N-Heterocyclic Carbene (NR,NH-NHC) Ligands 113
F. Ekkehardt Hahn
10 Cyclopentadienyl-functionalized N-Heterocyclic Carbene Complexes of Iron and Nickel: Catalysts for Reductions 133
Beatriz Royo
11 Palladium-(acyclic diaminocarbene) Species as Alternative to Palladium-(nitrogen heterocyclic carbenes) in Cross-coupling Catalysis 145
Vadim P. Boyarskiy, Konstantin V. Luzyanin, and Vadim Yu. Kukushkin
12 Synthesis of Metallocenes Via Metathesis in Metal Coordination Spheres 157
Antoni Pietrzykowski and W©©odzimierz Buchowicz
13 Metal-mediated [2 + 3] Dipolar Cycloaddition to Substrates with CN Triple Bond: Recent Advances 171
Konstantin V. Luzyanin and Maxim L. Kznetsov
14 Coordination Chemistry of Oxazoline/Thiazoline-based P,N Ligands 185
Shuanming Zhang, Roberto Pattacini, and Pierre Braunstein
15 “Click” Copper Catalyzed Azide-alkyne Cycloaddition (CuAAC) in Aqueous Medium 199
Joaqu´©¥n Garc´©¥a-A´lvarez and Jose´ Gimeno
16 Organogold Catalysis: Homogeneous Gold-catalyzed Transformations for a Golden Jubilee 207
Fabien Gagosz
17 Vanadium(IV) Complexes Derived from Aromatic o-Hydroxyaldehydes and Tyrosine Derivatives: Catalytic Evaluation in Sulfoxidations 227
Jo˜ao Costa Pessoa, Isabel Correia, and Pedro Ad˜ao
18 Microwave-assisted Catalytic Oxidation of Alcohols to Carbonyl Compounds 233
Yauhen Yu. Karabach, Maximilian N. Kopylovich, Kamran T. Mahmudov, and Armando J. L. Pombeiro
19 Oxidation of Glycerol with Hydrogen Peroxide Catalyzed by Metal Complexes 247
Dalmo Mandelli, Wagner A. Carvalho, Lidia S. Shul’pina, Alexander M. Kirillov, Marina V. Kirillova,
Armando J. L. Pombeiro, and Georgiy B. Shul’pin
20 Involvement of an Acetato Ligand in the Reductive Elimination Step of the Rhodium-catalyzed Methanol Carbonylation 259
Duc Hanh Nguyen, Nicolas Lassauque, Thomas Davin, Laurent Maron, Carole Le Berre, Philippe Serp, and Philippe Kalck
21 Half-sandwich Rhodium(III), Iridium(III), and Ruthenium(II) Complexes with Ancillary Pyrazole-based Ligands 269
Claudio Pettinari, Riccardo Pettinari, Corrado Di Nicola, and Fabio Marchetti
22 Carbon-scorpionate Complexes in Oxidation Catalysis 285
Lu´©¥sa M. D. R. S. Martins and Armando J. L. Pombeiro
23 Toward Chemoselective Bioconjugative Desulfitative Catalysis 295
Lanny S. Liebeskind and Ethel C. Garnier-Amblard
24 Sulfoxide Redox Chemistry with Molybdenum Catalysts 305
Maria Jos´e Calhorda and Luis F. Veiros
25 A New Family of Zirconium Complexes Anchored by Dianionic Cyclam-based Ligands: Syntheses,
Structures, and Catalytic Applications 315
Ana M. Martins, Rui F. Munh´a, Luis G. Alves, and Shanmuga Bharathi
26 Metal-organo Multicatalysis: An Emerging Concept 325
Alexandre F. Trindade, Jo˜ao N. Rosa, F´abio M. F. Santos, and Pedro M. P. Gois
PART III ORGANOMETALLIC POLYMERIZATION CATALYSIS 343
27 Coordinative Chain Transfer Polymerisations and Copolymerisations by Means of Rare Earths
Organometallic Catalysts for the Synthesis of Tailor-made Polymers 345
Marc Visseaux, Thomas Chenal, and Philippe Zinck
28 Charge-neutral and Cationic Complexes of Large Alkaline Earths for Ring-opening Polymerization
and Fine Chemicals Catalysis 359
Jean-Fran¸cois Carpentier, Bo Liu, and Yann Sarazin
PART IV ORGANOMETALLIC POLYMERS AND MATERIALS 379
29 Organometallic Polymers 381
Manuel Serrano-Ruiz, Franco Scalambra, and Antonio Romerosa
30 From Serendipity to Porosity: Synthesis and Reactivity of Coordination Polymers Based on Copper Trinuclear Triangular Motifs 407
Luciano Pandolfo
31 Organometallic Nanoparticles 421
Patricia Lara, Karine Philippot, Lise-Marie Lacroix, S´ebastien Lachaize, Nikos Liakakos, Katerina Soulantica, and Bruno Chaudret
32 Organometallic Compounds in the Synthesis of New Materials: Old Ligands, New Tricks 437
Piotr Sobota and ¨©ukasz John
33 The Role of Organometallic Complexes in the Synthesis of Shaped Carbon Materials 445
Neil J. Coville and Edward N. Nxumalo
34 Metal Catalysis in Fullerene Chemistry 459
Salvatore Filippone, Enrique E. Maroto, A´ngel Mart´©¥n-Domenech, and Nazario Mart´©¥n
35 Organometallic Complexes of Sumanene 473
Toru Amaya and Toshikazu Hirao
36 Advances in Luminescent Tetracoordinate Organoboron Compounds 485
D. Suresh and Pedro T. Gomes
37 Mechanochemistry: A Tool in the Synthesis of Catalysts, Metallodrugs, and Metallopharmaceuticals 493
Vˆania Andr´e, Clara S. B. Gomes, and M. Teresa Duarte
PART V ORGANOMETALLIC CHEMISTRY AND SUSTAINABLE ENERGY 501
38 Organometallic Complexes for Dye-sensitized Solar Cells (DSSC) 503
Delele W. Ayele, Wei-Nein Su, John Rick, Hung-Ming Chen, Chun-Jern Pan, Nibret G. Akalework, and Bing-Joe Hwang
39 Synthetic Photosynthesis for the Conversion of Large Volumes of Carbon Dioxide into Energy-Rich Molecules: Saving Fossil Fuels by Recycling Carbon 513
Michele Aresta and Angela Dibenedetto
40 Ionic Liquids for Hydrogen Storage: Opportunities for Organometallic Chemistry 529
Martin H. G. Prechtl and Sebastian Sahler
PART VI BIOORGANOMETALLIC CHEMISTRY 543
41 Metal Carbonyls for CO-based Therapies: Challenges and Successes 545
Carlos C. Rom˜ao and Helena L. A. Vieira
42 The Ferrocifen Family as Potent and Selective Antitumor Compounds: Mechanisms of Action 563
G´erard Jaouen and Siden Top
43 On the Track to Cancer Therapy: Paving New Ways With Ruthenium Organometallics 581
Tˆania S. Morais and M. Helena Garcia
44 Organometallic Chemistry of Rhenium and Technetium Fueled by Biomedical Applications 589
Ant´onio Paulo, Goreti Ribeiro Morais, and Isabel Santos
45 Metal-based Indolobenzazepines and Indoloquinolines: From Moderate cdk Inhibitors to Potential Antitumor Drugs 605
Michael F. Primik, Lukas K. Filak, and Vladimir B. Arion
46 Metal-based Chelates and Nanosystems as MRI Contrast Agents 619
Sara Figueiredo and Carlos F. G. C. Geraldes
PART VII ORGANOMETALLIC ELECTROCHEMISTRY 631
47 Electrochemistry and Supramolecular Interactions of “Ferrocifen” Anticancer Drugs with Cyclodextrins and Lipid Bilayers: An Electrochemical Overview 633
Olivier Buriez, Eric Labb´e, and Christian Amatore
48 Electrochemistry of Fischer Aminocarbene Complexes: Effects of Structure on Redox Properties, Electron Distribution, and Reaction Mechanisms 653
Ji¢§r´©¥ Ludv´©¥k and Irena Hoskovcov´a
49 Electron Transfer-induced Coordination Changes in Organometallic Complexes with Non-innocent Hemilabile Ligands 667
Wolfgang Kaim, Martina Bubrin, and Ralph H¨ubner
50 Redox Potential–Structure Relationships and Parameterization in Characterization and Identification of Organometallic Compounds 677
M. F´atima C. Guedes da Silva and Armando J. L. Pombeiro
51 Endohedral Metallofullerenes Today: More and More Versatile Ships in Multiform Bottles—Electrochemistry of X-Ray Characterized Monometallofullerenes 691
Fabrizia Fabrizi de Biani and Piero Zanello
POSTSCRIPT: A SHORT HISTORY OF THE ICOMC CONFERENCES 703
Ekkehardt Hahn
INDEX 707
