32 Topics in Organometallic Chemistry Editorial Board: M. Beller l J. M. Brown l P. H. Dixneuf A. Fu¨rstner l L. S. Hegedus l P. Hofmann T. Ikariya l L. A. Oro l M. Reetz l Q.-L. Zhou Topics in Organometallic Chemistry Recently Published Volumes C-X Bond Formation Dendrimer Catalysis Volume Editor: A. Vigalok Volume Editor: L. H. Gade Vol. 31, 2010 Vol. 20, 2006 Transition Metal Complexes of Neutral Metal Catalyzed Cascade Reactions h1-Carbon Ligands Volume Editor: T. J. J. Mu¨ller Volume Editors: R. Chauvin, Y. Canac Vol. 19, 2006 Vol. 30, 2010 Photophysics of Organometallics Catalytic Carbonylation Reactions Volume Editor: A. J. Lees Volume Editor: M. Beller Vol. 29, 2010 Vol. 18, 2006 Molecular Organometallic Materials Bioorganometallic Chemistry for Optics Volume Editor: G. Simonneaux Volume Editors: H. Le Bozec, V. Guerchais Vol. 17, 2006 Vol. 28, 2010 Conducting and Magnetic Organometallic Surface and Interfacial Organometallic Molecular Materials Chemistry and Catalysis Volume Editors: M. Fourmigue´, L. Ouahab Volume Editors: C. Cope´ret, B. Chaudret Vol. 27, 2009 Vol. 16, 2005 Metal Catalysts in Olefin Polymerization Chiral Diazaligands for Asymmetric Volume Editor: Z. Guan Synthesis Vol. 26, 2009 Volume Editors: M. Lemaire, P. Mangeney Bio-inspired Catalysts Vol. 15, 2005 Volume Editor: T. R. Ward Vol. 25, 2009 Palladium in Organic Synthesis Volume Editor: J. Tsuji Directed Metallation Vol. 14, 2005 Volume Editor: N. Chatani Vol. 24, 2007 Metal Carbenes in Organic Synthesis Regulated Systems for Multiphase Catalysis Volume Editor: K. H. Do¨tz Volume Editors: W. Leitner, M. Ho¨lscher Vol. 13, 2004 Vol. 23, 2008 Theoretical Aspects of Transition Metal Organometallic Oxidation Catalysis Catalysis Volume Editors: F. Meyer, C. Limberg Volume Editor: G. Frenking Vol. 22, 2007 Vol. 12, 2005 N-Heterocyclic Carbenes in Transition Metal Catalysis Ruthenium Catalysts and Fine Chemistry Volume Editor: F. Glorius Volume Editors: C. Bruneau, P. H. Dixneuf Vol. 21, 2006 Vol. 11, 2004 Medicinal Organometallic Chemistry Volume Editors: Ge´rard Jaouen and Nils Metzler-Nolte With Contributions by Roger Alberto Á Christophe Biot Á Angela Casini Á Daniel Dive Á Paul J. Dyson Á Ste´phane Gibaud Á Abraha Habtemariam Á Christian G. Hartinger Á Elizabeth A. Hillard Á Megan Hogan Á Ge´rard Jaouen Á Brian E. Mann Á Eric Meggers Á Seann P. Mulcahy Á Alexey A. Nazarov Á Nils Metzler-Nolte Á Ana M. Pizarro Á Peter J. Sadler Á Matthias Tacke Á Anne Vessie`res Editors Prof. Ge´rard Jaouen CNRS Laboratoire de Chimie et Biochimie des complexes moleculaires Ecole Nationale Superieure de Chimie de Paris 11 rue Pierre et Marie Curie 75231 Paris France [email protected] Prof. Dr. Nils Metzler-Nolte Lehrstuhl fu¨r Anorganische Chemie 1 Bioanorganische Chemie Ruhr-Universita¨t Bochum Universita¨tsstr. 150 44801 Bochum Germany [email protected] ISSN 1436-6002 e-ISSN 1616-8534 ISBN 978-3-642-13184-4 e-ISBN 978-3-642-13185-1 DOI 10.1007/978-3-642-13185-1 Springer Heidelberg Dordrecht London New York Library of Congress Control Number: 2010936349 # Springer-Verlag Berlin Heidelberg 2010 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. 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Cover design: Ku¨nkelLopka GmbH Printed on acid-free paper Springer is part of Springer Science+Business Media (www.springer.com) Volume Editors Prof. Ge´rard Jaouen Prof. Nils Metzler-Nolte CNRS Lehrstuhl fu¨r Anorganische Chemie 1 Laboratoire de Chimie et Biochimie Bioanorganische Chemie des complexes moleculaires Ruhr-Universita¨t Bochum Ecole Nationale Superieure de Chimie Universita¨tsstr. 150 de Paris 44801 Bochum 11 rue Pierre et Marie Curie Germany 75231 Paris [email protected] France [email protected] Editorial Board Prof. Matthias Beller Prof. Peter Hofmann Leibniz-Institut fu¨r Katalyse e.V. Organisch-Chemisches Institut an der Universita¨t Rostock Universita¨t Heidelberg Albert-Einstein-Str. 29a Im Neuenheimer Feld 270 18059 Rostock, Germany 69120 Heidelberg, Germany [email protected] [email protected] Prof. John M. Brown Prof. Takao Ikariya Chemistry Research Laboratory Department of Applied Chemistry Oxford University Graduate School of Science and Engineering Mansfield Rd., Tokyo Institute of Technology Oxford OX1 3TA, UK 2-12-1 Ookayama, Meguro-ku, [email protected] Tokyo 152-8550, Japan [email protected] Prof. Pierre H. Dixneuf Prof. Luis A. Oro Campus de Beaulieu Universite´ de Rennes 1 Instituto Universitario de Cata´lisis Homoge´nea Av. du Gl Leclerc Department of Inorganic Chemistry 35042 Rennes Cedex, France I.C.M.A. - Faculty of Science [email protected] University of Zaragoza-CSIC Zaragoza-50009, Spain Prof. Alois Fu¨rstner [email protected] Max-Planck-Institut fu¨r Kohlenforschung Prof. Manfred Reetz Kaiser-Wilhelm-Platz 1 45470 Mu¨lheim an der Ruhr, Germany Max-Planck-Institut fu¨r Kohlenforschung [email protected] Kaiser-Wilhelm-Platz 1 45470 Mu¨lheim an der Ruhr, Germany Prof. Louis S. Hegedus [email protected] Department of Chemistry Prof. Qi-Lin Zhou Colorado State University State Key Laboratory of Elemento-organic Fort Collins, Colorado 80523-1872, USA Chemistry [email protected] Nankai University Weijin Rd. 94, Tianjin 300071 PR China [email protected] v . Topics in Organometallic Chemistry Also Available Electronically Topics in Organometallic Chemistry is included in Springer’s eBook package Chemistry and Materials Science. If a library does not opt for the whole package the book series may be bought on a subscription basis. Also, all back volumes are available electronically. For all customers who have a standing order to the print version of Topics in Organometallic Chemistry, we offer the electronic version via SpringerLink free of charge. If you do not have access, you can still view the table of contents of each volume and the abstract of each article by going to the SpringerLink homepage, clicking on “Chemistry and Materials Science,” under Subject Collection, then “Book Series,” under Content Type and finally by selecting 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 by typing in Topics in Organometallic Chemistry. Color figures are published in full color in the electronic version on SpringerLink. Aims and Scope The series Topics in Organometallic Chemistry presents critical overviews of research results in organometallic chemistry. As our understanding of organometallic structures, properties and mechanisms grows, new paths 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 made 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. vii . Introduction Interdisciplinary research is increasing, and often actively encouraged, across many disciplines in the sciences. While this does not relieve individual researchers from the obligation to strive for originality and a deep understanding of their particular field of research, innovative concepts may emerge by combining seemingly incom- patible areas of research. One such area that seemed impossible to exist to many chemists only 20 years ago is Bioorganometallic Chemistry, i.e., the study of biological applications of organometallic compounds. An organometallic com- pound, by definition, contains at least one direct, covalent metal–carbon bond. As such, it was automatically felt to be sensitive to air and water and hence unsuitable for biological applications by the great majority of chemists. In 1985, an article appeared which used the term “bioorganometallic chemistry” in its introduction, and in 1986, the term was used in the title of a review article [1a, b], probably the first mentions of this term, probably the first mention of this term in a highly visible place. Admittedly, quite a few compounds and activities existed well before 1985, which we would, in hindsight, classify as bioorganome- tallic. Vitamin B12 (Fig. 1) and the whole family of cobalamins are arguably organometallic compounds with biological functions of highest importance, e.g., in amino acid and nucleotide biosynthesis. The body of a healthy human contains only a few mg of cobalamins, but even this small amount is absolutely necessary for the well-being and indeed survival of each of us. Dorothy Crowfoot Hodgkin, who solved the crystal structure of Vitamin B12, or cyanocobalamin, was awarded a Nobel Prize in Chemistry for this hallmark in structural chemistry in 1964. Even though the term did not even exist during her lifetime, Dorothy Hodgkin could thus be counted as a grandmother of bioorganometallic chemistry. While most scientists would likely find some ridicule in such a postmortem assignment of scientific achievements, it is also undoubtedly evident that the creation of a common intel- lectual roof – visible by a term or a prominent founding father – will promote and even induce research in a particular area.