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40 Topics in Organometallic Chemistry 40 Topics in Organometallic Chemistry Editorial Board: M. Beller l J. M. Brown l P. H. Dixneuf A. Fu¨rstner l L. Gooßen l L. S. Hegedus P. Hofmann l T. Ikariya l L. A. Oro l Q.-L. Zhou Topics in Organometallic Chemistry Recently Published Volumes Organometallics and Renewables Molecular Organometallic Materials Volume Editors: Michael A. R. Meier, for Optics Bert M. Weckhuysen, Pieter C. A. Bruijnincx Volume Editors: H. Le Bozec, V. Guerchais Vol. 39, 2012 Vol. 28, 2010 Transition Metal Catalyzed Enantioselective Conducting and Magnetic Organometallic Allylic Substitution in Organic Synthesis Molecular Materials Volume Editor: Uli Kazmaier Volume Editors: M. Fourmigue´, L. Ouahab Vol. 38, 2011 Vol. 27, 2009 Bifunctional Molecular Catalysis Volume Editors: T. Ikariya, M. Shibasaki Metal Catalysts in Olefin Polymerization Vol. 37, 2011 Volume Editor: Z. Guan Vol. 26, 2009 Asymmetric Catalysis from a Chinese Perspective Bio-inspired Catalysts Volume Editor: Shengming Ma Volume Editor: T. R. Ward Vol. 36, 2011 Vol. 25, 2009 Higher Oxidation State Organopalladium Directed Metallation and Platinum Chemistry Volume Editor: N. Chatani Volume Editor: A. J. Canty Vol. 24, 2007 Vol. 35, 2011 Iridium Catalysis Regulated Systems for Multiphase Catalysis Volume Editor: P. G. Andersson Volume Editors: W. Leitner, M. Ho¨lscher Vol. 34, 2011 Vol. 23, 2008 Iron Catalysis – Fundamentals and Organometallic Oxidation Catalysis Applications Volume Editors: F. Meyer, C. Limberg Volume Editor: B. Plietker Vol. 22, 2007 Vol. 33, 2011 N-Heterocyclic Carbenes in Transition Medicinal Organometallic Chemistry Metal Catalysis Volume Editors: G. Jaouen, N. Metzler-Nolte Volume Editor: F. Glorius Vol. 32, 2010 Vol. 21, 2006 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 h1-Carbon Ligands Metal Catalyzed Cascade Reactions Volume Editors: R. Chauvin, Y. Canac Volume Editor: T. J. J. Mu¨ller Vol. 30, 2010 Vol. 19, 2006 Photophysics of Organometallics Catalytic Carbonylation Reactions Volume Editor: A. J. Lees Volume Editor: M. Beller Vol. 29, 2010 Vol. 18, 2006 Organometallic Pincer Chemistry Volume Editors: Gerard van Koten Á David Milstein With Contributions by A. Castonguay Á S.L. Craig Á L. Dosta´l Á G.R. Freeman Á J.A. Gareth Williams Á D. Gelman Á K.I. Goldberg Á J.L. Hawk Á D.M. Heinekey Á J.-i. Ito Á R. Jambor Á D. Milstein Á H. Nishiyama Á E. Poverenov Á D.M. Roddick Á R. Romm Á D.M. Spasyuk Á A. St. John Á K.J. Szabo´ Á G. van Koten Á D. Zargarian Editors Gerard van Koten David Milstein Organic Chemistry & Catalysis The Weizmann Institute of Science Debye Institute for Nanomaterials Science The Kimmel Center for Molecular Design Faculty of Science Department of Organic Chemistry Utrecht University Rehovot Utrecht Israel Netherlands ISBN 978-3-642-31080-5 ISBN 978-3-642-31081-2 (eBook) DOI 10.1007/978-3-642-31081-2 Springer Heidelberg New York Dordrecht London Library of Congress Control Number: 2012948954 # Springer-Verlag Berlin Heidelberg 2013 This work is subject to copyright. All rights are reserved by the Publisher, whether the whole or part of the material is concerned, specifically the rights of translation, reprinting, reuse of illustrations, recitation, broadcasting, reproduction on microfilms or in any other physical way, and transmission or information storage and retrieval, electronic adaptation, computer software, or by similar or dissimilar methodology now known or hereafter developed. Exempted from this legal reservation are brief excerpts in connection with reviews or scholarly analysis or material supplied specifically for the purpose of being entered and executed on a computer system, for exclusive use by the purchaser of the work. Duplication of this publication or parts thereof is permitted only under the provisions of the Copyright Law of the Publisher’s location, in its current version, and permission for use must always be obtained from Springer. Permissions for use may be obtained through RightsLink at the Copyright Clearance Center. Violations are liable to prosecution under the respective Copyright Law. The use of general descriptive names, registered names, trademarks, service marks, 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. While the advice and information in this book are believed to be true and accurate at the date of publication, neither the authors nor the editors nor the publisher can accept any legal responsibility for any errors or omissions that may be made. The publisher makes no warranty, express or implied, with respect to the material contained herein. Printed on acid-free paper Springer is part of Springer Science+Business Media (www.springer.com) Volume Editors Gerard van Koten David Milstein Organic Chemistry & Catalysis The Weizmann Institute of Science Debye Institute for Nanomaterials Science The Kimmel Center for Molecular Design Faculty of Science Department of Organic Chemistry Utrecht University Rehovot Utrecht Israel Netherlands [email protected] [email protected] Editorial Board Prof. Matthias Beller Prof. Louis S. Hegedus Leibniz-Institut fu¨r Katalyse e.V. Department of Chemistry an der Universita¨t Rostock Colorado State University Albert-Einstein-Str. 29a Fort Collins, Colorado 80523-1872, USA 18059 Rostock, Germany [email protected] [email protected] Prof. Peter Hofmann Prof. John M. Brown Organisch-Chemisches Institut Chemistry Research Laboratory Universita¨t Heidelberg Oxford University Im Neuenheimer Feld 270 Mansfield Rd., 69120 Heidelberg, Germany Oxford OX1 3TA, UK [email protected] [email protected] Prof. Takao Ikariya Prof. Pierre H. Dixneuf Department of Applied Chemistry Graduate School of Science and Engineering Campus de Beaulieu Tokyo Institute of Technology Universite´ de Rennes 1 2-12-1 Ookayama, Meguro-ku, Av. du Gl Leclerc Tokyo 152-8552, Japan 35042 Rennes Cedex, France [email protected] [email protected] Prof. Luis A. Oro Prof. Alois Fu¨rstner Instituto Universitario de Cata´lisis Homoge´nea Max-Planck-Institut fu¨r Kohlenforschung Department of Inorganic Chemistry Kaiser-Wilhelm-Platz 1 I.C.M.A. - Faculty of Science 45470 Mu¨lheim an der Ruhr, Germany University of Zaragoza-CSIC [email protected] Zaragoza-50009, Spain [email protected] Prof. Lukas J. Gooßen Prof. Qi-Lin Zhou FB Chemie - Organische Chemie State Key Laboratory of Elemento-organic TU Kaiserslautern Chemistry Erwin-Schro¨dinger-Str. Geb. 54 Nankai University 67663 Kaiserslautern, German Weijin Rd. 94, Tianjin 300071 PR China [email protected] [email protected] . 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 free access to the electronic volumes of the Series published in the current year via SpringerLink. 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. From volume 29 onwards this series is listed with ISI/Web of Knowledge and in coming years it will acquire an impact factor. vii . Preface Privileged ligands play a key role in the development of organometallic chemistry, homogeneous catalysis and metal-mediated and -catalysed organic synthesis. Among the monoanionic, multidentate ligands, the Cyclopentadienyl (Cp) frag- ment is no doubt the most frequently used metal-binding platform. In fact, the hallmark isolation and structural elucidation of ferrocene represented a key bench- mark moment in the development of organometallic chemistry [1]. In recent times, monoanionic Pincer [2] ligands have also become one of the priviliged ligand platforms and are being used with increasing success; indeed sometimes astonishing results in all the three of the fields mentioned above can be realised with a single pincer framework. In a similar fashion to the Cp ligands, the Pincers bind to a metal centre as a multidentate ligand but, in addition, often engenders a number of unanticipated properties both in the way it interacts and also interplays with the metal fragment(s). In this book, we focus on pincer ligands of the type ECE0 (Fig. 1). Initially, Pincer ligands had been designed simply as platforms intended to enforce trans-spanning bisphosphine (PCP [3]) or bis-sulphide donors (SCS [4]) or to act as a rigid mer-tridentate (NCN [5, 6]) ligand.
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