346 Topics in Current Chemistry
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1 346 Topics in Current Chemistry Editorial Board: H. Bayley, Oxford, UK K.N. Houk, Los Angeles, CA, USA G. Hughes, CA, USA C.A. Hunter, Sheffield, UK K. Ishihara, Chikusa, Japan M.J. Krische, Austin, TX, USA J.-M. Lehn, Strasbourg Cedex, France R. Luque, Córdoba, Spain M. Olivucci, Siena, Italy J.S. Siegel, Nankai District, China J. Thiem, Hamburg, Germany M. Venturi, Bologna, Italy C.-H. Wong, Taipei, Taiwan H.N.C. Wong, Shatin, Hong Kong
2 Aims and Scope The series Topics in Current Chemistry presents critical reviews of the present and future trends in modern chemical research. The scope of coverage includes all areas of chemical science including the interfaces with related disciplines such as biology, medicine and materials science. The goal of each thematic volume is to give the non-specialist reader, whether at the university or in industry, a comprehensive overview of an area where new insights are emerging that are of interest to larger scientific audience. Thus each review within the volume critically surveys one aspect of that topic and places it within the context of the volume as a whole. The most significant developments of the last 5 to 10 years should be presented. A description of the laboratory procedures involved is often useful to the reader. The coverage should not be exhaustive in data, but should rather be conceptual, concentrating on the methodological thinking that will allow the non-specialist reader to understand the information presented. Discussion of possible future research directions in the area is welcome. Review articles for the individual volumes are invited by the volume editors. Readership: research chemists at universities or in industry, graduate students. More information about this series at
3 Guangbin Dong Editor C-C Bond Activation With contributions by N. Cramer A. Dermenci G. Dong C.J. Douglas A.M. Dreis X.-F. Fu Y. Gao W.D. Jones C.-H. Jun J.S. Kingsbury D.C. Moebius Y. Nakao J.-W. Park E. Parker V.L. Rendina L. Souillart T. Xu Z.-X. Yu
4 Editor Guangbin Dong The University of Texas at Austin Department of Chemistry & Biochemistry Austin USA ISSN ISSN (electronic) ISBN ISBN (ebook) DOI / Springer Heidelberg New York Dordrecht London Library of Congress Control Number: Springer-Verlag Berlin Heidelberg 2014 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 (
5 Preface Stimulated by the need for green and more efficient approaches to functionalize hydrocarbon feedstocks, the vast development of carbon hydrogen (C H) bond activation has been evident in the past decade. In contrast, the related chemical processes involving activating carbon carbon (C C) bonds, another equally abundant chemical bond, have received much less attention until recently. The reason why C C bond activation has been overlooked is straightforward. It is widely accepted that C C bond formation is central to organic synthesis, such as cross-coupling, cycloaddition, alkylation, and aldol reactions; this is a constructive process. The question is why would people want to cleave C C bonds? Is it a destructive process? As the editor of this volume, I hope by reading these contributions you will realize the answer to this question is clearly no. From a historical viewpoint, C C bond cleavage reactions, such as sigmatropic rearrangements (e.g., Cope and Claisen rearrangements), retro-aldol, ozonolysis of alkenes, Beckman rearrangement, etc., have found broad applications in complex molecule synthesis. With the expansion of organotransition metal chemistry in the last 30 years, the unique reactivity of organometallic species adds new possibilities to this field. The goal of modern C C bond activation is far from just splitting one molecule into two; instead, it converts relatively simple compounds into more complex, often value-added, products. More frequently, breaking one C C bond allows two or more new C C (or C X) bonds to form, as shown in many chapters of this volume. Overall, C C bond activation can not just be highly constructive; it can also provide opportunities to develop novel transformations through employing such distinct modes of reactivity. This volume contains eight chapters from leading experts in the field, and is expected to provide an overview of the latest developments in C C bond activation. It begins with mechanistic studies of transition metal-mediated C C bond action by Prof. W.D. Jones, which laid the foundation for further discovery of catalytic reactions. The following chapters from Profs. Y. Nakao, C.-H. Jun, and C. J. Douglas focus on different strategies to activate unstrained C C bonds, namely, C CN bond activation, metal-organic cooperative catalysis, and activation of 8-acylquinolines. v
6 vi Preface The volume then slightly shifts direction to a Lewis acid-catalyzed diazoalkane carbonyl homologation reaction by Prof. J.S. Kingsbury, followed by a thorough discussion of asymmetric transformations via C C bond cleavage contributed by Prof. N. Cramer. The volume closes with two chapters covering activation of strained-ring systems: cycloaddition of cyclopropanes from Prof. Z. Yu and activation of four-membered cyclic ketones from my own research group. As the editor, I am grateful to all the contributors for providing such high quality and in-depth review chapters. I am also indebted to Prof. M.J. Krische s recommendation for taking on this task. Given limited space and time, unfortunately, not all the important contributions in the field could be included, e.g., oxidative C C bond cleavage and decarboxylation reactions. I apologize for omitting these efforts in this short volume. Austin, USA February 2014 Guangbin Dong
7 Contents Mechanistic Studies of Transition Metal-Mediated C C Bond Activation... 1 William D. Jones Catalytic C CN Bond Activation Yoshiaki Nakao Metal Organic Cooperative Catalysis in C C Bond Activation Chul-Ho Jun and Jung-Woo Park Carbon Carbon Bond Activation with 8-Acylquinolines Ashley M. Dreis and Christopher J. Douglas Catalysis of Diazoalkane Carbonyl Homologation. How New Developments in Hydrazone Oxidation Enable the Carbon Insertion Strategy for Synthesis David C. Moebius, Victor L. Rendina, and Jason S. Kingsbury Asymmetric Transformations via C C Bond Cleavage Laetitia Souillart, Evelyne Parker, and Nicolai Cramer Transition Metal-Catalyzed Cycloadditions of Cyclopropanes for the Synthesis of Carbocycles: C C Activation in Cyclopropanes Yang Gao, Xu-Fei Fu, and Zhi-Xiang Yu Transition Metal-Catalyzed C C Bond Activation of Four-Membered Cyclic Ketones Tao Xu, Alpay Dermenci, and Guangbin Dong Index vii
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