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17 Topics in Organometallic Chemistry Editorial Board: J M Brown · P H Dixneuf · A Fürstner · L S Hegedus P Hofmann · P Knochel · G van Koten · S Murai · M Reetz Topics in Organometallic Chemistry Recently Published and Forthcoming Volumes Organometallic Oxidations Catalysis Volume Editors: F Meyer, C Limberg Vol 22, 2006 Theoretical Aspects of Transition Metal Catalysis Volume Editor: G Frenking Vol 12, 2005 N-Heterocyclic Carbenes (NHC) in Transition Metal Catalysis Volume Editor: F Glorius Vol 21, 2006 Ruthenium Catalysts and Fine Chemistry Volume Editors: C Bruneau, P H Dixneuf Vol 11, 2004 Dendrimer Catalysis Volume Editor: L H Gade Vol 20, 2006 Metal Catalyzed Cascade Reactions Volume Editor: T J J Müller Vol 19, 2006 Catalytic Carbonylation Reactions Volume Editor: M Beller Vol 18, 2006 Bioorganometallic Chemistry Volume Editor: G Simonneaux Vol 17, 2006 Surface and Interfacial Organometallic Chemistry and Catalysis Volume Editors: C Copéret, B Chaudret Vol 16, 2005 Chiral Diazaligands for Asymmetric Synthesis Volume Editors: M Lemaire, P Mangeney Vol 15, 2005 Palladium in Organic Synthesis Volume Editor: J Tsuji Vol 14, 2005 Metal Carbenes in Organic Synthesis Volume Editor: K H Dötz Vol 13, 2004 New Aspects of Zirconium Containing Organic Compounds Volume Editor: I Marek Vol 10, 2004 Precursor Chemistry of Advanced Materials CVD, ALD and Nanoparticles Volume Editor: R Fischer Vol 9, 2005 Metallocenes in Stereoselective Synthesis Volume Editor: T Takahashi Vol 8, 2004 Transition Metal Arene π-Complexes in Organic Synthesis and Catalysis Volume Editor: E P Kündig Vol 7, 2004 Organometallics in Process Chemistry Volume Editor: R D Larsen Vol 6, 2004 Organolithiums in Enantioselective Synthesis Volume Editor: D M Hodgson Vol 5, 2003 Organometallic Bonding and Reactivity: Fundamental Studies Volume Editor: J M Brown, P Hofmann Vol 4, 1999 Activation of Unreactive Bonds and Organic Synthesis Volume Editor: S Murai Vol 3, 1999 Bioorganometallic Chemistry Volume Editor: Gérard Simonneaux With contributions by C S Allardyce · P A Butler · P J Dyson · J C Fontecilla-Camps B Kräutler · T Hirao · P Le Maux · T Moriuchi · K Severin G Simonneaux · A Volbeda 123 The series Topics in Organometallic Chemistry presents critical overviews of research results in organometallic chemistry As our understanding of organometallic structure, properties and mechanisms increases, new ways are opened for the design of organometallic compounds and reactions tailored to the needs of such diverse areas as organic synthesis, medical research, biology and materials science Thus the scope of coverage includes a broad range of topics of pure and applied organometallic chemistry, where new breakthroughs are being achieved that are of significance to a larger scientific audience The individual volumes of Topics in Organometallic Chemistry are thematic Review articles are generally invited by the volume editors In references Topics in Organometallic Chemistry is abbreviated Top Organomet Chem and is cited as a journal Springer WWW home page: springer.com Visit the TOMC content at springerlink.com Library of Congress Control Number: 2006924680 ISSN 1436-6002 ISBN-10 3-540-33047-X Springer Berlin Heidelberg New York ISBN-13 978-3-540-33047-9 Springer Berlin Heidelberg New York DOI 10.1007/b97910 This work is subject to copyright All rights are reserved, whether the whole or part of the material is concerned, specifically the rights of translation, reprinting, reuse of illustrations, recitation, broadcasting, reproduction on microfilm or in any other way, and storage in data banks Duplication of this publication or parts thereof is permitted only under the provisions of the German Copyright Law of September 9, 1965, in its current version, and permission for use must always be obtained from Springer Violations are liable for prosecution under the German Copyright Law Springer is a part of Springer Science+Business Media springer.com c Springer-Verlag Berlin Heidelberg 2006 Printed in Germany The use of registered names, trademarks, etc in this publication does not imply, even in the absence of a specific statement, that such names are exempt from the relevant protective laws and regulations and therefore free for general use Cover design: Design & Production GmbH, Heidelberg Typesetting and Production: LE-TEX Jelonek, Schmidt & Vöckler GbR, Leipzig Printed on acid-free paper 02/3141 YL – Volume Editor Gérard Simonneaux DR CNRS (UMR 6226) Bât 10C pièce 126 Campus de Beaulieu 35042 Rennes Cedex, France gerard.simonneaux@univ-rennes1.fr Editorial Board Dr John M Brown Prof Pierre H Dixneuf Dyson Perrins Laboratory South Parks Road Oxford OX13QY john.brown@chem.ox.ac.uk Campus de Beaulieu Université de Rennes Av du Gl Leclerc 35042 Rennes Cedex, France Pierre.Dixneuf@univ-rennesl.fr Prof Alois Fürstner Max-Planck-Institut für Kohlenforschung Kaiser-Wilhelm-Platz 45470 Mülheim an der Ruhr, Germany fuerstner@mpi-muelheim.mpg.de Prof Peter Hofmann Organisch-Chemisches Institut Universität Heidelberg Im Neuenheimer Feld 270 69120 Heidelberg, Germany ph@phindigo.oci.uni-heidelberg.de Prof Gerard van Koten Department of Metal-Mediated Synthesis Debye Research Institute Utrecht University Padualaan 3584 CA Utrecht, The Netherlands vankoten@xray.chem.ruu.nl Prof Manfred Reetz Max-Planck-Institut für Kohlenforschung Kaiser-Wilhelm-Platz 45470 Mülheim an der Ruhr, Germany reetz@mpi.muelheim.mpg.de Prof Louis S Hegedus Department of Chemistry Colorado State University Fort Collins, Colorado 80523-1872 USA hegedus@lamar.colostate.edu Prof Paul Knochel Fachbereich Chemie Ludwig-Maximilians-Universität Butenandstr 5–13 Gebäude F 81377 München, Germany knoch@cup.uni-muenchen.de Prof Shinji Murai Faculty of Engineering Department of Applied Chemistry Osaka University Yamadaoka 2-1, Suita-shi Osaka 565 Japan murai@chem.eng.osaka-u.ac.jp Topics in Organometallic Chemistry Also Available Electronically For all customers who have a standing order to Topics in Organometallic Chemistry, we offer the electronic version via SpringerLink free of charge Please contact your librarian who can receive a password or free access to the full articles by registering at: springerlink.com If you not have a subscription, you can still view the tables of contents of the volumes and the abstract of each article by going to the SpringerLink Homepage, clicking on “Browse by Online Libraries”, then “Chemical Sciences”, and finally choose Topics in Organometallic Chemistry You will find information about the – – – – Editorial Board Aims and Scope Instructions for Authors Sample Contribution at springer.com using the search function Preface One of the more recently developing areas of organometallic chemistry, indeed in all of chemistry, is that of its applications to living systems The name bioorganometallics applied to compounds with metal–carbon bonds and organometallic reactions have found a place in living systems In this book, you will find general overviews of selected in vivo processes presented from the viewpoint of the biochemist, and the study of organometallic complexes of biological and medical interest Naturally occurring bioorganometallic complexes, such as vitamin B12, are first considered The B12 -coenzymes are the organometallic cofactors in various important enzymatic reactions and are particularly relevant in the metabolism of archaea and (other) anaerobic microorganisms Surprising characteristics of recently discovered iron and nickel hydrogenases, including a possible role in the geochemical theory of the origin of life, are highlighted The possible formation of carbene complexes of cytochrome P450 enzymes in various metabolisms of xenobiotics is also discussed Bioorganometallic chemistry is envisioned to provide not only organometallic receptors such as polynuclear organometallic macrocycles for biologically interesting molecules but also ferrocene–peptide bioconjugates giving a peptidomimetic basis for protein folding These chapters illustrate the usefulness of organometallic complexes in water as a molecular scaffold, a sensitive probe, a chromophore, an NMR shift reagent, a redox-active site and a chemosensor One of the other major areas of bioorganometallic compounds originated in a possible use of these complexes as therapeutic drugs Thus the medicinal properties of organometallic compounds are reviewed, with notable applications in the treatment and diagnosis of cancer and in the treatment of viral, fungal, bacterial and parasitic infections This monograph is not intended to provide a comprehensive view of all explored fields of research activity in bioorganometallic chemistry However, the reader will get a balanced view of this rapidly developing and promising area I hope this book will stimulate its readers to enter the exciting field of bioorganometallic chemistry Rennes, France, April 2006 Gérard Simonneaux Contents Biological Organometallic Chemistry of B12 P A Butler · B Kräutler Catalytic Nickel–Iron–Sulfur Clusters: From Minerals to Enzymes A Volbeda · J C Fontecilla-Camps 57 Carbene Complexes of Heme Proteins and Iron Porphyrin Models G Simonneaux · P Le Maux 83 Organometallic Receptors for Biologically Interesting Molecules K Severin 123 Ferrocene–Peptide Bioconjugates T Moriuchi · T Hirao 143 Medicinal Properties of Organometallic Compounds C S Allardyce · P J Dyson 177 Author Index Volumes 1–17 211 Subject Index 219 208 C.S Allardyce · P.J Dyson 163 Hubel R, Polborn K, Knizek J, Noth H, Beck W (2000) Zeitschrift für anorganische und allgemeine Chemie 626:1701 164 Popova LV, Babin VN, Belousov YA, Nekrasov YS, Snegireva AE, Borodina NP, Shaposhnikova GM, Bychenko OB, Raevskii PM (1993) Appl Organomet Chem 7:85 165 Koepf-Maier P, Koepf H, Neuse EW (1984) J Cancer Res Clin 108:336 166 Henderson W, Alley SR (2001) Inorg Chim Acta 322:106 167 Top S, Vessières A, Cabestaing C, Laios I, 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Cancer Chemoth Pharm 24:302 229 Giraldi T, Sava G, Bertoli G, Mestroni G, Zassinovich G (1977) Cancer Res 37:2662 230 Buckley RG, Elsome AM, Fricker SP, Henderson GR, Theobald BR, Parish RV, Howe BP, Kelland LR (1996) J Med Chem 39:5208 231 Parish RV, Howe BP, Wright JP, Mack J, Pritchard RG, Buckley RG, Elsome AM, Fricker SP (1996) Inorg Chem 35:1659 232 Navarro M, Pérez H, Sánchez-Delgado RA (1997) J Med Chem 40:1937 233 Shapiro DL, Masci JR (1996) J Rheumatology 23:1818 234 Tepperman K, Shinju Y, Roy PW, Floyd R, Zhao Z, Dorsey J, Elder RC (1994) Met Based Drugs 1:433 235 Bernstein LR, Reed DE (1998) Pub Int Appl PCT/US97/11220 210 C.S Allardyce · P.J Dyson 236 Dimartino MJ, Lee JC, Badger AM, Murhead KA, Mirabelli CK, Hanna N (1986) J Pharma Exp Thera 236:103 237 Slavik M, Elias L, Mrema J, Saiers JH (1982) Drug Exp Clin Res 8:379 238 Atteke C, Ndong JMM, Aubouy A, Naciejewski L, Brocard J, Lebibi J, Deloron P (2003) J Antimicrobial Chemotherapy 51:1021 239 Mariet F, Brosser P (1991) Pharmaceutica Acta Helvetiae 66:60 240 Sweiry JH, Mann GE (1991) Am J Physiol 261:G685 241 Oreshkin AE, Myasishcheva NV (1990) B Exp Biol Med 109:957 242 Schenk BE, Festen HPM, Kuipers EJ, Klinkenberg-Knol EC, Meuwissen SGM (1996) Aliment Pharm Therap 10:541 243 Deutsch E, Bushong W, Glavan KA, Elder RC, Sodd VJ, Scholz KL, Fortman DL, Lukes SJ (1981) Science 214:85 Author Index Volumes 1–17 The volume numbers are printed in italics Abdel-Magid AF, see Mehrmann SJ (2004) 6: 153–180 Akiyama K, see Mikami M (2005) 14: 279–322 Allardyce CS, Dyson PJ (2006) Medicinal Properties of Organometallic Compounds 17: 177–210 Alper H, see Grushin VV (1999) 3: 193–225 Anwander R (1999) Principles in Organolanthanide Chemistry 2: 1–62 Arends IWCE, Kodama T, Sheldon RA (2004) Oxidations Using Ruthenium Catalysts 11: 277–320 Armentrout PB (1999) Gas-Phase Organometallic Chemistry 4: 1–45 Barluenga J, Rodríguez F, Fanás FJ, Flórez J (2004) Cycloaddition Reaction of Group Fischer Carbene Complexes 13: 59–121 Basset J-M, see Candy J-P (2005) 16: 151–210 Beak P, Johnson TA, Kim DD, Lim SH (2003) Enantioselective Synthesis by Lithiation Adjacent to Nitrogen and Electrophile Incorporation 5: 139–176 Bertus P, see Szymoniak J (2005) 10: 107–132 Bien J, Lane GC, Oberholzer MR (2004) Removal of Metals from Process Streams: Methodologies and Applications 6: 263–284 Blechert S, Connon SJ (2004) Recent Advances in Alkene Metathesis 11: 93–124 Bonino F, see Bordiga S (2005) 16: 37–68 Bordiga S, Damin A, Bonino F, Lamberti C (2005) Single Site Catalyst for Partial Oxidation Reaction: TS-1 Case Study 16: 37–68 Böttcher A, see Schmalz HG (2004) 7: 157–180 Braga D (1999) Static and Dynamic Structures of Organometallic Molecules and Crystals 4: 47–68 Breuzard JAJ, Christ-Tommasino ML, Lemaire M (2005) Chiral Ureas and Thiroureas in Asymmetric Catalysis 15: 231–270 Brüggemann M, see Hoppe D (2003) 5: 61–138 Bruneau C (2004) Ruthenium Vinylidenes and Allenylidenes in Catalysis 11: 125–153 Brutchey RL, see Fujdala KL (2005) 16: 69–115 Butler PA, Kräutler B (2006) Biological Organometallic Chemistry of B12 17: 1–55 Candy J-P, Copéret C, Basset J-M (2005) Analogy between Surface and Molecular Organometallic Chemistry 16: 151–210 Catellani M (2005) Novel Methods of Aromatic Functionalization Using Palladium and Norbornene as a Unique Catalytic System 14: 21–54 Chatani N (2004) Selective Carbonylations with Ruthenium Catalysts 11: 173–195 Chatani N, see Kakiuchi F (2004) 11: 45–79 212 Author Index Volumes 1–17 Chaudret B (2005) Synthesis and Surface Reactivity of Organometallic Nanoparticles 16: 233–259 Chlenov A, see Semmelhack MF (2004) 7: 21–42 Chlenov A, see Semmelhack MF (2004) 7: 43–70 Chinkov M, Marek I (2005) Stereoselective Synthesis of Dienyl Zirconocene Complexes 10: 133–166 Christ-Tommasino ML, see Breuzard JAJ (2005) 15: 231–270 Chuzel O, Riant O (2005) Sparteine as a Chiral Ligand for Asymmetric Catalysis 15: 59–92 Clayden J (2003) Enantioselective Synthesis by Lithiation to Generate Planar or Axial Chirality 5: 251–286 Connon SJ, see Blechert S (2004) 11: 93–124 Copéret C, see Candy J-P (2005) 16: 151–210 Cummings SA, Tunge JA, Norton JR (2005) Synthesis and Reactivity of Zirconaaziridines 10: 1–39 Damin A, see Bordiga S (2005) 16: 37–68 Damin A, see Zecchina A (2005) 16: 1–35 Delaude L, see Noels A (2004) 11: 155–171 Dedieu A (1999) Theoretical Treatment of Organometallic Reaction Mechanisms and Catalysis 4: 69–107 Delmonte AJ, Dowdy ED, Watson DJ (2004) Development of Transition Metal-Mediated Cyclopropanation Reaction 6: 97–122 Demonceau A, see Noels A (2004) 11: 155–171 Derien S, see Dixneuf PH (2004) 11: 1–44 Deubel D, Loschen C, Frenking G (2005) Organometallacycles as Intermediates in OxygenTransfer Reactions Reality or Fiction? 12: 109–144 Dixneuf PH, Derien S, Monnier F (2004) Ruthenium-Catalyzed C–C Bond Formation 11: 1–44 Dötz KH, Minatti A (2004) Chromium-Templated Benzannulation Reactions 13: 123–156 Dowdy EC, see Molander G (1999) 2: 119–154 Dowdy ED, see Delmonte AJ (2004) 6: 97–122 Doyle MP (2004) Metal Carbene Reactions from Dirhodium(II) Catalysts 13: 203–222 Drudis-Solé G, Ujaque G, Maseras F, Lledós A (2005) Enantioselectivity in the Dihydroxylation of Alkenes by Osmium Complexes 12: 79–107 Dyson PJ, see Allardyce CS (2006) 17: 177–210 Eisen MS, see Lisovskii A (2005) 10: 63–105 Fañanás FJ, see Barluenga (2004) 13: 59–121 Flórez J, see Barluenga (2004) 13: 59–121 Fontecave M, Hamelin O, Ménage S (2005) Chiral-at-Metal Complexes as Asymmetric Catalysts 15: 271–288 Fontecilla-Camps JC, see Volbeda A (2006) 17: 57–82 Fraile JM, García JI, Mayoral JA (2005) Non-covalent Immobilization of Catalysts Based on Chiral Diazaligands 15: 149–190 Frenking G, see Deubel D (2005) 12: 109–144 Freund H-J, see Risse T (2005) 16: 117–149 Fu GC, see Netherton M (2005) 14: 85–108 Author Index Volumes 1–17 213 Fujdala KL, Brutchey RL, Tilley TD (2005) Tailored Oxide Materials via Thermolytic Molecular Precursor (TMP) Methods 16: 69–115 Fürstner A (1998) Ruthenium-Catalyzed Metathesis Reactions in Organic Synthesis 1: 37–72 García JI, see Fraile JM (2005) 15: 149–190 Gates BC (2005) Oxide- and Zeolite-supported “Molecular” Metal Clusters: Synthesis, Structure, Bonding, and Catalytic Properties 16: 211–231 Gibson SE (née Thomas), Keen SP (1998) Cross-Metathesis 1: 155–181 Gisdakis P, see Rösch N (1999) 4: 109–163 Görling A, see Rösch N (1999) 4: 109–163 Goldfuss B (2003) Enantioselective Addition of Organolithiums to C=O Groups and Ethers 5: 12–36 Gossage RA, van Koten G (1999) A General Survey and Recent Advances in the Activation of Unreactive Bonds by Metal Complexes 3: 1–8 Gotov B, see Schmalz HG (2004) 7: 157–180 Gras E, see Hodgson DM (2003) 5: 217–250 Grepioni F, see Braga D (1999) 4: 47–68 Gröger H, see Shibasaki M (1999) 2: 199–232 Groppo E, see Zecchina A (2005) 16: 1–35 Grushin VV, Alper H (1999) Activation of Otherwise Unreactive C–Cl Bonds 3: 193–225 Guitian E, Perez D, Pena D (2005) Palladium-Catalyzed Cycloaddition Reactions of Arynes 14: 109–146 Hamelin O, see Fontecave M (2005) 15: 271–288 Harman D (2004) Dearomatization of Arenes by Dihapto-Coordination 7: 95–128 Hatano M, see Mikami M (2005) 14: 279–322 He Y, see Nicolaou KC (1998) 1: 73–104 Hegedus LS (2004) Photo-Induced Reactions of Metal Carbenes in organic Synthesis 13: 157–201 Hermanns J, see Schmidt B (2004) 13: 223–267 Hidai M, Mizobe Y (1999) Activation of the N–N Triple Bond in Molecular Nitrogen: Toward its Chemical Transformation into Organo-Nitrogen Compounds 3: 227–241 Hirao T, see Moriuchi T (2006) 17: 143–175 Hodgson DM, Stent MAH (2003) Overview of Organolithium-Ligand Combinations and Lithium Amides for Enantioselective Processes 5: 1–20 Hodgson DM, Tomooka K, Gras E (2003) Enantioselective Synthesis by Lithiation Adjacent to Oxygen and Subsequent Rearrangement 5: 217–250 Hoppe D, Marr F, Brüggemann M (2003) Enantioselective Synthesis by Lithiation Adjacent to Oxygen and Electrophile Incorporation 5: 61–138 Hou Z, Wakatsuki Y (1999) Reactions of Ketones with Low-Valent Lanthanides: Isolation and Reactivity of Lanthanide Ketyl and Ketone Dianion Complexes 2: 233–253 Hoveyda AH (1998) Catalytic Ring-Closing Metathesis and the Development of Enantioselective Processes 1: 105–132 Huang M, see Wu GG (2004) 6: 1–36 Hughes DL (2004) Applications of Organotitanium Reagents 6: 37–62 Iguchi M,Yamada K,Tomioka K (2003) Enantioselective Conjugate Addition and 1,2-Addition to C=N of Organolithium Reagents 5: 37–60 Ito Y, see Murakami M (1999) 3: 97–130 214 Author Index Volumes 1–17 Ito Y, see Suginome M (1999) 3: 131–159 Itoh K, Yamamoto Y (2004) Ruthenium Catalyzed Synthesis of Heterocyclic Compounds 11: 249–276 Jacobsen EN, see Larrow JF (2004) 6: 123–152 Johnson TA, see Break P (2003) 5: 139–176 Jones WD (1999) Activation of C–H Bonds: Stoichiometric Reactions 3: 9–46 Kagan H, Namy JL (1999) Influence of Solvents or Additives on the Organic Chemistry Mediated by Diiodosamarium 2: 155–198 Kakiuchi F, Murai S (1999) Activation of C–H Bonds: Catalytic Reactions 3: 47–79 Kakiuchi F, Chatani N (2004) Activation of C–H Inert Bonds 11: 45–79 Kanno K, see Takahashi T (2005) 8: 217–236 Keen SP, see Gibson SE (née Thomas) (1998) 1: 155–181 Kendall C, see Wipf P (2005) 8: 1–25 Kiessling LL, Strong LE (1998) Bioactive Polymers 1: 199–231 Kim DD, see Beak P (2003) 5: 139–176 King AO, Yasuda N (2004) Palladium-Catalyzed Cross-Coupling Reactions in the Synthesis of Pharmaceuticals 6: 205–246 King NP, see Nicolaou KC, He Y (1998) 1: 73–104 Kobayashi S (1999) Lanthanide Triflate-Catalyzed Carbon–Carbon Bond-Forming Reactions in Organic Synthesis 2: 63–118 Kobayashi S (1999) Polymer-Supported Rare Earth Catalysts Used in Organic Synthesis 2: 285–305 Kodama T, see Arends IWCE (2004) 11: 277–320 Kondratenkov M, see Rigby J (2004) 7: 181–204 Koten G van, see Gossage RA (1999) 3: 1–8 Kotora M (2005) Metallocene-Catalyzed Selective Reactions 8: 57–137 Kräutler B, see Butler PA (2006) 17: 1–55 Kumobayashi H, see Sumi K (2004) 6: 63–96 Kündig EP (2004) Introduction 7: 1–2 Kündig EP (2004) Synthesis of Transition Metal η6 -Arene Complexes 7: 3–20 Kündig EP, Pape A (2004) Dearomatization via η6 Complexes 7: 71–94 Lamberti C, see Bordiga S (2005) 16: 37–68 Lane GC, see Bien J (2004) 6: 263–284 Larock R (2005) Palladium-Catalyzed Annulation of Alkynes 14: 147–182 Larrow JF, Jacobsen EN (2004) Asymmetric Processes Catalyzed by Chiral (Salen)Metal Complexes 6: 123–152 Lemaire M, see Breuzard JAJ (2005) 15: 231–270 Li CJ,Wang M (2004) Ruthenium Catalyzed Organic Synthesis in Aqueous Media 11: 321–336 Li Z, see Xi Z (2005) 8: 27–56 Lim SH, see Beak P (2003) 5: 139–176 Lin Y-S, Yamamoto A (1999) Activation of C–O Bonds: Stoichiometric and Catalytic Reactions 3: 161–192 Lisovskii A, Eisen MS (2005) Octahedral Zirconium Complexes as Polymerization Catalysts 10: 63–105 Lledós A, see Drudis-Solé G (2005) 12: 79–107 Loschen C, see Deubel D (2005) 12: 109–144 Author Index Volumes 1–17 215 Ma S (2005) Pd-catalyzed Two or Three-component Cyclization of Functionalized Allenes 14: 183–210 Mangeney P, see Roland S (2005) 15: 191–229 Marciniec B, Pretraszuk C (2004) Synthesis of Silicon Derivatives with Ruthenium Catalysts 11: 197–248 Marek I, see Chinkov M (2005) 10: 133–166 Marr F, see Hoppe D (2003) 5: 61–138 Maryanoff CA, see Mehrmann SJ (2004) 6: 153–180 Maseras F (1999) Hybrid Quantum Mechanics/Molecular Mechanics Methods in Transition Metal Chemistry 4: 165–191 Maseras F, see Drudis-Solé G (2005) 12: 79–107 Le Maux P, see Simonneaux G (2006) 17: 83–122 Mayoral JA, see Fraile JM (2005) 15: 149–190 Medaer BP, see Mehrmann SJ (2004) 6: 153–180 Mehrmann SJ, Abdel-Magid AF, Maryanoff CA, Medaer BP (2004) Non-Salen Metal-Catalyzed Asymmetric Dihydroxylation and Asymmetric Aminohydroxylation of Alkenes Practical Applications and Recent Advances 6: 153–180 De Meijere, see Wu YT (2004) 13: 21–58 Ménage S, see Fontecave M (2005) 15: 271–288 Michalak A, Ziegler T (2005) Late Transition Metal as Homo- and Co-Polymerization Catalysts 12: 145–186 Mikami M, Hatano M, Akiyama K (2005) Active Pd(II) Complexes as Either Lewis Acid Catalysts or Transition Metal Catalysts 14: 279–322 Minatti A, Dötz KH (2004) Chromium-Templated Benzannulation Reactions 13: 123–156 Miura M, Satoh T (2005) Catalytic Processes Involving b-Carbon Elimination 14: 1–20 Miura M, Satoh T (2005) Arylation Reactions via C–H Bond Cleavage 14: 55–84 Mizobe Y, see Hidai M (1999) 3: 227–241 Molander G, Dowdy EC (1999) Lanthanide- and Group Metallocene Catalysis in Small Molecule Synthesis 2: 119–154 Monnier F, see Dixneuf (2004) 11: 1–44 Mori M (1998) Enyne Metathesis 1: 133–154 Mori M (2005) Synthesis and Reactivity of Zirconium-Silene Complexes 10: 41–62 Moriuchi T, Hirao T (2006) Ferrocene–Peptide Bioconjugates 17: 143–175 Morokuma K, see Musaev G (2005) 12: 1–30 Mulzer J, Öhler E (2004) Olefin Metathesis in Natural Product Syntheses 13: 269–366 Muñiz K (2004) Planar Chiral Arene Chromium (0) Complexes as Ligands for Asymetric Catalysis 7: 205–223 Murai S, see Kakiuchi F (1999) 3: 47–79 Murakami M, Ito Y (1999) Cleavage of Carbon–Carbon Single Bonds by Transition Metals 3: 97–130 Musaev G, Morokuma K (2005) Transition Metal Catalyzed s-Bond Activation and Formation Reactions 12: 1–30 Nakamura I, see Yamamoto Y (2005) 14: 211–240 Nakamura S, see Toru T (2003) 5: 177–216 Namy JL, see Kagan H (1999) 2: 155–198 Negishi E, Tan Z (2005) Diastereoselective, Enantioselective, and Regioselective Carboalumination Reactions Catalyzed by Zirconocene Derivatives 8: 139–176 Netherton M, Fu GC (2005) Palladium-catalyzed Cross-Coupling Reactions of Unactivated Alkyl Electrophiles with Organometallic Compounds 14: 85–108 216 Author Index Volumes 1–17 Nicolaou KC, King NP, He Y (1998) Ring-Closing Metathesis in the Synthesis of Epothilones and Polyether Natural Products 1: 73–104 Nishiyama H (2004) Cyclopropanation with Ruthenium Catalysts 11: 81–92 Noels A, Demonceau A, Delaude L (2004) Ruthenium Promoted Catalysed Radical Processes toward Fine Chemistry 11: 155–171 Nolan SP, Viciu MS (2005) The Use of N-Heterocyclic Carbenes as Ligands in Palladium Mediated Catalysis 14: 241–278 Normant JF (2003) Enantioselective Carbolithiations 5: 287–310 Norton JR, see Cummings SA (2005) 10: 1–39 Oberholzer MR, see Bien J (2004) 6: 263–284 Öhler E, see Mulzer J (2004) 13: 269–366 Pape A, see Kündig EP (2004) 7: 71–94 Pawlow JH, see Tindall D, Wagener KB (1998) 1: 183–198 Pena D, see Guitian E (2005) 14: 109–146 Perez D, see Guitian E (2005) 14: 109–146 Prashad M (2004) Palladium-Catalyzed Heck Arylations in the Synthesis of Active Pharmaceutical Ingredients 6: 181–204 Prestipino C, see Zecchina A (2005) 16: 1–35 Pretraszuk C, see Marciniec B (2004) 11: 197–248 Riant O, see Chuzel O (2005) 15: 59–92 Richmond TG (1999) Metal Reagents for Activation and Functionalization of Carbon– Fluorine Bonds 3: 243–269 Rigby J, Kondratenkov M (2004) Arene Complexes as Catalysts 7: 181–204 Risse T, Freund H-J (2005) Spectroscopic Characterization of Organometallic Centers on Insulator Single Crystal Surfaces: From Metal Carbonyls to Ziegler–Natta Catalysts 16: 117–149 Rodríguez F, see Barluenga (2004) 13: 59–121 Roland S, Mangeney P (2005) Chiral Diaminocarbene Complexes, Synthesis and Application in Asymmetric Catalysis 15: 191–229 Rösch N (1999) A Critical Assessment of Density Functional Theory with Regard to Applications in Organometallic Chemistry 4: 109–163 Roucoux A (2005) Stabilized Noble Metal Nanoparticles: An Unavoidable Family of Catalysts for Arene Derivative Hydrogenation 16: 261–279 Sakaki S (2005) Theoretical Studies of C–H s-Bond Activation and Related by TransitionMetal Complexes 12: 31–78 Satoh T, see Miura M (2005) 14: 1–20 Satoh T, see Miura M (2005) 14: 55–84 Savoia D (2005) Progress in the Asymmetric Synthesis of 1,2-Diamines from Azomethine Compounds 15: 1–58 Schmalz HG, Gotov B, Böttcher A (2004) Natural Product Synthesis 7: 157–180 Schmidt B, Hermanns J (2004) Olefin Metathesis Directed to Organic Synthesis: Principles and Applications 13: 223–267 Schrock RR (1998) Olefin Metathesis by Well-Defined Complexes of Molybdenum and Tungsten 1: 1–36 Author Index Volumes 1–17 217 Schulz E (2005) Use of N,N-Coordinating Ligands in Catalytic Asymmetric C–C Bond Formations: Example of Cyclopropanation, Diels–Alder Reaction, Nucleophilic Allylic Substitution 15: 93–148 Semmelhack MF, Chlenov A (2004) (Arene)Cr(Co)3 Complexes: Arene Lithiation/Reaction with Electrophiles 7: 21–42 Semmelhack MF, Chlenov A (2004) (Arene)Cr(Co)3 Complexes: Aromatic Nucleophilic Substitution 7: 43–70 Sen A (1999) Catalytic Activation of Methane and Ethane by Metal Compounds 3: 81–95 Severin K (2006) Organometallic Receptors for Biologically Interesting Molecules 17: 123– 142 Sheldon RA, see Arends IWCE (2004) 11: 277–320 Shibasaki M, Gröger H (1999) Chiral Heterobimetallic Lanthanoid Complexes: Highly Efficient Multifunctional Catalysts for the Asymmetric Formation of C–C, C–O and C–P Bonds 2: 199–232 Simonneaux G, Le Maux P (2006) Carbene Complexes of Heme Proteins and Iron Porphyrin Models 17: 83–122 Staemmler V (2005) The Cluster Approach for the Adsorption of Small Molecules on Oxide Surfaces 12: 219–256 Stent MAH, see Hodgson DM (2003) 5: 1–20 Strassner T (2004) Electronic Structure and Reactivity of Metal Carbenes 13: 1–20 Strong LE, see Kiessling LL (1998) 1: 199–231 Suginome M, Ito Y (1999) Activation of Si–Si Bonds by Transition-Metal Complexes 3: 131–159 Sumi K, Kumobayashi H (2004) Rhodium/Ruthenium Applications 6: 63–96 Suzuki N (2005) Stereospecific Olefin Polymerization Catalyzed by Metallocene Complexes 8: 177–215 Szymoniak J, Bertus P (2005) Zirconocene Complexes as New Reagents for the Synthesis of Cyclopropanes 10: 107–132 Takahashi T, Kanno K (2005) Carbon–Carbon Bond Cleavage Reaction Using Metallocenes 8: 217–236 Tan Z, see Negishi E (2005) 8: 139–176 Tilley TD, see Fujdala KL (2005) 16: 69–115 Tindall D, Pawlow JH, Wagener KB (1998) Recent Advances in ADMET Chemistry 1: 183–198 Tobisch S (2005) Co-Oligomerization of 1,3-Butadiene and Ethylene Promoted by Zerovalent ‘Bare’ Nickel Complexes 12: 187–218 Tomioka K, see Iguchi M (2003) 5: 37–60 Tomooka K, see Hodgson DM (2003) 5: 217–250 Toru T, Nakamura S (2003) Enantioselective Synthesis by Lithiation Adjacent to Sulfur, Selenium or Phosphorus, or without an Adjacent Activating Heteroatom 5: 177–216 Tunge JA, see Cummings SA (2005) 10: 1–39 Uemura M (2004) (Arene)Cr(Co)3 Complexes: Cyclization, Cycloaddition and Cross Coupling Reactions 7: 129–156 Ujaque G, see Drudis-Solé G (2005) 12: 79–107 Viciu MS, see Nolan SP (2005) 14: 241–278 Volbeda A, Fontecilla-Camps JC (2006) Catalytic Nickel–Iron–Sulfur Clusters: From Minerals to Enzymes 17: 57–82 218 Author Index Volumes 1–17 Wagener KB, see Tindall D, Pawlow JH (1998) 1: 183–198 Wakatsuki Y, see Hou Z (1999) 2: 233–253 Wang M, see Li CJ (2004) 11: 321–336 Watson DJ, see Delmonte AJ (2004) 6: 97–122 Wipf P, Kendall C (2005) Hydrozirconation and Its Applications 8: 1–25 Wu GG, Huang M (2004) Organolithium in Asymmetric Process 6: 1–36 Wu YT, de Meijere A (2004) Versatile Chemistry Arising from Unsaturated Metal Carbenes 13: 21–58 Xi Z, Li Z (2005) Construction of Carbocycles via Zirconacycles and Titanacycles 8: 27–56 Yamada K, see Iguchi M (2003) 5: 37–60 Yamamoto A, see Lin Y-S (1999) 3: 161–192 Yamamoto Y, see Itoh K (2004) 11: 249–276 Yamamoto Y, Nakamura I (2005) Nucleophilic Attack by Palladium Species 14: 211–240 Yasuda H (1999) Organo Rare Earth Metal Catalysis for the Living Polymerizations of Polar and Nonpolar Monomers 2: 255–283 Yasuda N, see King AO (2004) 6: 205–246 Zecchina A, Groppo E, Damin A, Prestipino C (2005) Anatomy of Catalytic Centers in Phillips Ethylene Polymerization Catalyst 16: 1–35 Ziegler T, see Michalak A (2005) 12: 145–186 Subject Index Acetogens 57 Acetyl CoA synthase 57, 68 Adenosine -monophosphate 124 Albumin 179 Alkoxy-α-diazo-β-ketoesters 111 Alkylcobalt(III) 189, 192 Alkylthiolates 101 Alkyltin(IV) 189 Alzheimer’s disease 130 Amino acids 123 – –, molecular recognition 127 Amino mutases, B12 -dependent 41 2-Aminobenzoic acid 127 Aminosidine 184 Amphotericin B 184 Anti-HIV drugs, protease-targeting 186 Antimalarials 184 Antimonials 184 Antimony compounds, leishmaniasis 178 Antimony-N,N-piperazinedithiocarbamate 201 Antipernicious anemia factor Arsenic 182 Arsephenamaine, syphilis 178 Auranofin 201, 202 Aurocyanide 201 Azaspirane 202 B12 , electrochemistry 13 –, structure/reactivity –, toxicology 44 Benznidazole 200 1,3-Benzodioxole derivatives 88 Bis-1,1 -disubstituted-ferrocenyl carbohydrazone 195 Bis(oxazolinyl)pyridine (pybox) series 105 Brugia pahangi 185 N-t-Butyl-α-phenyl nitrone 91 CaMg6 FeSi12 O24 (diopside) 61 Carbene transfer 110 Carbenes ligands, heme proteins 85 – –, iron porphyrins 92 – –, ruthenium/osmium porphyrins 103 Carbethoxycarbenes 113 Carbon monoxide 197 – –, dehydrogenase 57, 62 Carbon tetrachloride 86 Carboplatin 178 Carboxydothermus hydrogenoformans 63 Carboxydotrophic bacteria 58 Cardiolite 203 Cephalosporine 183 CFCl3 88 CH3 SH 59 Chemosensors 123 Chlorocarbenes 94 Chloroguanide 184 Chloroquine 180 Cisplatin 178 Co-57-cyanocobalamin 202 Co(cyclam)(H2 O)(Me) 189, 199 Cobalt Cobalt–carbon bond 84 Cobalt-corrinoids Cobamides, kinetic redox properties 17 –, thermodynamic redox properties 14 CODH, catalytic cycle 74 – /ACS 58, 68 Coenzyme B12 1, 4, 84 –, -dependent enzymes 31 CoFeSP 62 Conocarpan 114 Corrinoids 26 Cyanocob(III)alamin Cyano-8-epicobalamin 220 Cycloaddition transformation, tandem 115 Cyclopentadienyl (Cp) 145 Cyclopropanation 110 Cysteine thiolates 64 Cytochrome P450 85 Daunorubicin 186 DDT (2,2-bis (p-chlorophenyl)-1,1,1-trichloroethane) 94 Dehalogenases, reductive, B12 -dependent 43 Dehalogenation, polyhalogenated compounds 86 -Deoxyadenosine 124 Desulfomicrobium baculatum 64 Desulfovibrio spp 63 Dialkyl ruthenium(IV) porphyrin 104 Dicobalthexacarbonylalkyne agent 199 Diethyl maleate/fumarate 110 Dihydroxypyridine ligands 129 Diisopropyl diazomethylphosphonate 114 Diol dehydratases 39 Diphenyl-dithiocarbamate 186 Dipyridine dichloroplatinum 178 Dithiocarbamate 186 DNA, platinated 179 Epindolidione 145 Ethanolamine ammonia lyase 39 Ethyl diazoacetate 114 9-Ethylhypoxanthin 124 Ferratricarbaboranes 193 Ferrocene-peptide bioconjugates 143 Ferrocenyl gold 190 Ferrocenyl oestrogen mimic 190 Ferrocenyl-cephalosporin 183 Ferrocenyl-chloroquine 183 Ferrocenyl-penicillin 183 Ferrocenylalanine 145 FeS 58 Fluoride ions, selective recognition/sensing 133 Folate synthesis 200 Glutamate mutase 36 Glutathione S-transferase 186 Glycine ethyl esters 114 Subject Index Gold [1,3-(dimesitylmethylimidazolinium)] chloride 194 Greigite 61 Halothane 87 Helminth parasites 185 Heme proteins, bioorganometallic catalysis 116 Hemoglobin 91 Histidine 135 HIV, protease 189 –, protease inhibitors 89 –, protease-targeting 186 –, reverse transcriptase inhibitor 112 Host-guest chemistry, trinuclear/metallamacrocyclic hosts 124 Hydrogen bonding 143 Hydrogenase 57 –, H2 -sensing 64 Indicator displacement assays, organometallic complex 135 Indomethacin 202 Iridium 124, 185 Iridium-COD-pentamidine 183 Iron porphyrin 83 Iron(II) tetraarylporphyrins 96 Iron-sulfur 61 Isocyanides 101 Leishmaniasis 184 –, antimony compounds 178 Lipid peroxidation 86 Lithium 123 –, selective recognition/sensing 129 Malaria 180 Mefloquine 189 Metal carbonyl anticancer/diagnosis compounds 199 Metal cyanides 198 Metal sulfides 60 Metal tricarbonyl-cyclopentadienyl 199 Metallacrown complexes 129 Metallamacrocycles 123 Metalloporphyrins 84, 92 –, carbene transfer 110 Methanogens 63 Subject Index Methanosarcina thermophila 62, 69 Methionine 135 Methionine synthase 29 Methyl group transfer Methyl transferases, B12 -dependent 27 9-Methyladenine 124 Methylenedioxyphenyl HIV protease inhibitors 89 Methyl-group transfer, B12 -cofactors 30 Methylmalonyl-CoA mutase 34 MgFeSiO3 (orthopyroxene) 61 Mn2 (CO)10 197 Molinema dessetae 185 Monoxygenase systems 86 Moorella thermoacetica 62 Multidrug resistance 186 Mutases 34 Myoglobin 91, 116 NAMI-A 191 1-Naphthoic acid 128 Nedaplatin 178 Ni(III)-peroxide 69 Nickel superoxide dismutase 69 NiFe hydride 73 [NiFe]-hydrogenase, catalytic cycle 72 NiFeS enzymes 57 Nifurtimox 200 Niridazole 200 Norpseudovitamin B12 Nucleoside kinases 195 Organo-gold 201 Organo-gold(III) 189 Organometallic benzimidazole 185 Organometallic electrochemical synthesis 19 Organo-osmium 185 Organo-palladium 180 Origin of life, Geochemical theory 57 Osmium 108 Osmium meso-tetra-p-tolyl-porphyrin carbene 108 Osmium ylide 108 Oxaliplatin 178 Palladium 180 Penicillin 183, 187 Pentacarbonylrhenate 96 Pentamidine 184, 185 221 Peptides 123 –, histidine-/methionine-containing, chemosensor 135 –, molecular recognition 127 Peroxidases 116 Phenobarbital 202 Phenytoin 202 Pincer silver(I)-carbene 196 Plasmodium falciparum 180 Platin 178 Platinum(IV) complex 179 Polio, type 188 Polyhalogenated compounds, dehalogenation 86 Pseudovitamin B12 Pyrimethamine 184 Pyrite 61 Radical reactions – –, B12 coenzymes 42 Ralstonia eutropha 64 RAPTA 193, 201 Receptors 123 Redox-switching 143 Reverse transcriptase 189 Rhodium 124 Rhodium chloroquine 183 Rhodium-cycloocta-1,5-diene 200 Rhodium-2-hydroxybenzothiazole 201 Ribonucleotide reductase, B12 -dependent 41 Ru(arene)Cl2(pta) 192 [Ru(CO)3 Cl2 ]2 197 Ruthenium 103, 124 Ruthenium-aminobenzothiazole 185 Ruthenium(II)-arene 191 Ruthenium myoglobin/hemoglobin 116 Ruthenium tripodal phosphine 194 Satraplatin 178 Selenium 182 Selenocarbonyl 95 Serpentine 61 Sigmatropic rearrangements 114 Silver nitrate 196 Silylcarbene ferroporphyrin 96 Sodium nitroprusside 197 Spirobifluorenylporphyrins 112 Spirogermanium 189, 201 Sulfamethoxydiazine 186 222 Sulfonamides 184 Syphilis, arsephenamaine 178 Tandem carbonyl ylide formation 115 Technecium-isonitrile 202 Tetrafluorenylporphyrins 112 Tetrapyrroles Thimerosal (sodium ethylmercurithiosalicylate) 180 Thiocarbonyl complexes 95 Titanocene dichloride 190 (TPP)Fe(CCl2) 94 Transferrin 179, 190 Transplatin 179 Tricarbonyl η5 -cyclopentadienyl manganese 202 Trichloromethyl trimethylsilane 96 Trifluoro diazoethane 87 Subject Index Trinuclear, metallamacrocyclic hosts 124 Triphenylphosphinegold(I)-chloroquine 180 Trypanosoma cruzi 185 Tryptophan 127 Vanadocene 188 Vanadocene dithiocarbamate 195 Verapamil 186 11-Vertex ferratricarbaborane 193 Vinylidene carbene 94 N-Vinylprotoporphyrin 90 Vitamin B12 WHI-07 188 Ylides 108, 114 ... Beller Vol 18, 2006 Bioorganometallic Chemistry Volume Editor: G Simonneaux Vol 17, 2006 Surface and Interfacial Organometallic Chemistry and Catalysis Volume Editors: C Copéret, B Chaudret Vol. .. audience The individual volumes of Topics in Organometallic Chemistry are thematic Review articles are generally invited by the volume editors In references Topics in Organometallic Chemistry is abbreviated... K Severin G Simonneaux · A Volbeda 123 The series Topics in Organometallic Chemistry presents critical overviews of research results in organometallic chemistry As our understanding of organometallic
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