Topics in Current Chemistry

Transcription

1 224 Topics in Current Chemistry Editorial Board: A. de Meijere K.N. Houk. H. Kessler ].-M. Lehn- S.V. Ley. S.L. Schreiber J. Thiem B. M. Trost E V6gtle H. Yamamoto

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3 Hypervalent Iodine Chemistry Modern Developments in Organic Synthesis Volume Editor: Thomas Wirth With contributions by. Kita, G. E Koser, M. Ochiai, H. Tohma, A. Varvoglis, T. Wirth, V. V. Zhdankin ~ Springer

4 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 nonspecialist reader, whether at the university or in industry, a comprehensive overview of an area where new insights are emerging that are of interest to a larger scientific audience. As a rule, contributions are specially commissioned. The editors and publishers will, however, always be pleased to receive suggestions and supplementary information. Papers are accepted for Topics in Current Chemistry in English. In references Topics in Current Chemistry is abbreviated Top. Curr. Chem. and is cited as a journal. Springer WWW home page: Visit the TCC home page at or ISSN ISBN Springer-Verlag Berlin Heidelberg New York Library of Congress Catalog Card Number 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 microfilms or in any other ways, and storage in data banks. Duplication of this publication or parts thereof is only permitted 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- Verlag.Violations are liable for prosecution under the German Copyright Law. Springer-Verlag Berlin Heidelberg New York a member of BertetsmannSpringer Science+Business Media GmbH Springer-Verlag Berlin Heidelberg 2003 Printed in Germany 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: Friedhelm Steinen-Broo, Barcelona; MEDIO, Berlin Typesetting: Fotosatz-Service K6hler GmbH, Wfirzburg SPIN: /3020 ra Printed on acid-free paper

5 Volume Editor Prof. Dr. Thomas Wirth Department of Chemistry Cardiff University CF 10 3TB Cardiff, United Kingdom E-maih Editorial Board Prof. Dr. Armin de Meijere Institut ffir Organische Chemie der Georg-August-Universit/it Tammannstrat]e G6ttingen, Germany E-maih ameijer ingen.de Prof. Dr. Horst Kessler Institut ffir Organische Chemie TU Mfinchen Lichtenbergstrat~e Garching, Germany kessler@ch.tum.de Prof. Steven V. Ley University Chemical Laboratory Lensfield Road Cambridge CB2 1EW, Great Britain E-maih svllooo@cus.cam.ac.uk Prof. Dr. Joachim Thiem Institut fiir Organische Chemie Universit/it Hamburg Martin-Luther-King-Platz Hamburg, Germany thiem@chemie.uni-hamburg.de Prof. Dr. Fritz V6gtle Kekul&Institut ffir Organische Chemie und Biochemie der Universit~it Bonn Gerhard-Domagk-Strat~e Bonn, Germany '. voegtle@uni-bonn.de Prof. K.N. Houk Department of Chemistry and Biochemistry University of California 405 Hflgard Avenue Los Angeles, CA , USA houk@chem.ucla.edu Prof. Jean-Marie Lehn Institut de Chimie Universit~ de Strasbourg 1 rue Blaise Pascal, B.P. Z 296/R Strasbourg Cedex, France E-maih lehn@chimie.u-strasbg.fr Prof. Stuart L. Schreiber Chemical Laboratories Harvard University 12 Oxford Street Cambridge, MA , USA E-maih sls@slsiris.harvard.edu Prof. Barry M. Trost Department of Chemistry Stanford University Stanford, CA , USA E-maih bmtrost@leland.stanford.edu Prof. Hisashi Yamamoto School of Engineering Nagoya University Chikusa, Nagoya , Japan E-maih j45988a@nucc.cc.nagoya-u.ac.jp

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7 Preface The pioneers of hypervalent iodine chemistry have already realized that the chemistry of iodine(u1) and iodine(v)-containing compounds offers multiple advantages over established methods. A wide range of reactions is possible, oxidations and C-C-coupling reactions under extremely mild reaction conditions and with a broad tolerance of other functional groups being the most prominent ones. The various findings in, and applications of, the chemistry with hypervalent iodine compounds has led, in recent years, to a tremendous growth which is reflected by the large number of publications in this field. However, the last comprehensive compilation of hyper valent iodine chemistry appeared more than five years ago. We felt that there is a need for an update. I am grateful to the distinguished scientists, who contributed, with their skill and expertise, the various chapters of this volume. By emphasizing the developments in hypervalent iodine chemistry over the last couple of years, this volume presents a comprehensive overview of the various facets, scope, and limitations of organic chemistry with hypervalent iodine compounds. Cardiff, July 2002 Thomas Wirth

8 Contents Introduction and General Aspects T. Wirth Reactivities, Properties and Structures M. Ochiai Preparation of Hypervalent Iodine Compounds A. Varvoglis C-C Bond Forming Reactions V.V. Zhdankin C-Heteroatom-Bond Forming Reactions G. E Koser Heteroatom-Heteroatom-Bond Forming Reactions G.E Koser Oxidations and Rearrangements T. Wirth Synthetic Applications (Total Synthesis and Natural Product Synthesis) H. Tohma, Y. Kita Author Index Volumes Subject Index

9 Contents of Volume 208 Organoselenium Chemistry Modern Developments in Organic Synthesis Volume Editor: Thomas Wirth ISBN Introduction and General Aspects T. Wirth Electrophilic Selenium, Selenocyclizations M. Tiecco Nucleophilic Selenium M. Iwaoka, S. Tomoda Radical Reactions Using Selenium Precursors P. Renaud Selenium-Stabilized Carbanions S. Ponthieux, C. Paulmier Selenium at Higher Oxidation States J. Drabowicz, M. Mikohjczyk Selenocarbonyls T. Mural, S. Kato Selenoxide Elimination and [2,3] Sigmatropic Rearrangements Y. Nishibayashi, S. Uemura Selenium Compounds as Ligands and Catalysts. Nishibayashi, S. Uemura