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30 Topics in Organometallic Chemistry 30 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 and Forthcoming Volumes Photophysics of Organometallics Catalytic Carbonylation Reactions Volume Editor: Alistair 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 Surface and Interfacial Organometallic Conducting and Magnetic Organometallic Chemistry and Catalysis Molecular Materials Volume Editors: C. Cope´ret, B. Chaudret ´ Volume Editors: M. Fourmigue, L. Ouahab Vol. 16, 2005 Vol. 27, 2009 Chiral Diazaligands for Asymmetric Metal Catalysts in Olefin Polymerization Synthesis Volume Editor: Z. Guan Volume Editors: M. Lemaire, P. Mangeney Vol. 26, 2009 Vol. 15, 2005 Bio-inspired Catalysts Volume Editor: T. R. Ward Palladium in Organic Synthesis Vol. 25, 2009 Volume Editor: J. Tsuji Vol. 14, 2005 Directed Metallation Volume Editor: N. Chatani Metal Carbenes in Organic Synthesis Vol. 24, 2007 Volume Editor: K. H. Do¨tz Vol. 13, 2004 Regulated Systems for Multiphase Catalysis Volume Editors: W. Leitner, M. Ho¨lscher Theoretical Aspects of Transition Metal Vol. 23, 2008 Catalysis Volume Editor: G. Frenking Organometallic Oxidation Catalysis Vol. 12, 2005 Volume Editors: F. Meyer, C. Limberg Vol. 22, 2007 Ruthenium Catalysts and Fine Chemistry N-Heterocyclic Carbenes in Transition Volume Editors: C. Bruneau, P. H. Dixneuf Metal Catalysis Vol. 11, 2004 Volume Editor: F. Glorius New Aspects of Zirconium Containing Vol. 21, 2006 Organic Compounds Dendrimer Catalysis Volume Editor: I. Marek Volume Editor: L. H. Gade Vol. 10, 2004 Vol. 20, 2006 Precursor Chemistry of Advanced Materials Metal Catalyzed Cascade Reactions CVD, ALD and Nanoparticles Volume Editor: T. J. J. Mu¨ller Volume Editor: R. Fischer Vol. 19, 2006 Vol. 9, 2005 Transition Metal Complexes of Neutral Z1-Carbon Ligands Volume Editors: Remi Chauvin and Yves Canac With Contributions by Antoine Baceiredo Á Victorio Cadierno Á Yves Canac Á Remi Chauvin Á Gernot Frenking Á Sergio E. Garcı´a-Garrido Á F. Ekkehardt Hahn Á Mareike C. Jahnke Á Tsuyoshi Kato Á Christine Lepetit Á Eddy Maerten Á Wolfgang Petz Á Esteban P. Urriolabeitia Editors Professor Remi Chauvin Dr. Yves Canac Universite´ Paul Sabatier Universite´ Paul Sabatier Laboratoire de Chimie de Coordination Laboratoire de Chimie de Coordination du CNRS, UPR 8241 du CNRS, UPR 8241 205 route de Narbonne 205 route de Narbonne 31077 Toulouse cedex 4 31077 Toulouse cedex 4 France France [email protected] [email protected] ISSN 1436-6002 e-ISSN 1616-8534 ISBN 978-3-642-04721-3 e-ISBN 978-3-642-04722-0 DOI 10.1007/978-3-642-04722-0 Springer Heidelberg Dordrecht London New York Library of Congress Control Number: 2009941065 # 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. 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 to prosecution under the German Copyright Law. The use of general descriptive names, 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: Ku¨nkelLopka GmbH; volume cover: SPi Publisher Services Printed on acid-free paper Springer is part of Springer Science+Business Media (www.springer.com) Volume Editors Prof. Remi Chauvin Dr. Yves Canac Universite´ Paul Sabatier Universite´ Paul Sabatier Laboratoire de Chimie de Coordination Laboratoire de Chimie de Coordination du CNRS, UPR 8241 du CNRS, UPR 8241 205 route de Narbonne 205 route de Narbonne 31077 Toulouse cedex 4 31077 Toulouse cedex 4 France France [email protected] [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 Preface Metal–carbon bonds are gems of the organic chemistry toolbox, serving to activate octet-covalent carbon centers, and stabilize their resulting non-octet covalent elec- tronic structure in the jewel cases of diffuse transition metal orbitals. Whereas many criteria are used for general ligand classifications (coordinating function, donor/ acceptor character,...), a further simple analogy among carbon ligands allows quite different classical representatives such as NHCs, ylides, and cumulenylidenes to be placed in the category of neutral Z1-carbon ligands. Their internal typology is based on the three fundamental hybridization states of covalent carbon atoms (sp3, sp2, sp), and is refined according to the number of conjugated heteroatoms, such as nitrogen or phosphorus. The three types and six subtypes of ligands are thus put together for the first time under the unifying heading of this volume. The seven chapters are not primarily dedicated to provide extensive reviews, but to illustrate synergetically how the cognate ligands share common features that could inspire the design of novel or mixed representatives for targeted applications. After the reign of sp2 and sp3 N and P ligands in the realm of catalysis, spectator C-ligands recently entered through the sp2 gate with the tremendous achievements of the NHC family. While other sp2, sp3, and sp families still remain as infant pretenders, the present categorization might help their advent in the design of future catalysts. The Editors gratefully acknowledge Springer, in particular M. Hertel, and all the contributors for their interest and
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