Hypervalent Iodine Chemistry: Modern Developments in Organic Synthesis PDF
Preview Hypervalent Iodine Chemistry: Modern Developments in Organic Synthesis
224 scipoT ni 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 regnirpS nilreB grebledieH New kroY Kong Hong nodnoL Milan siraP oykoT tnelavrepyH Iodine yrtsimehC Modern stnempoleveD ni Organic sisehtnyS Volume Editor: Thomas Wirth With contributions by .¥ Kita, .G E Koser, .M Ochiai, H. Tohma, .A Varvoglis, .T Wirth, .V .V Zhdankin r e g n~ i r p S The series in Topics 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 comprehensivoev erview ofa n 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 in Current Topics Chemistry in English. In references Topics in Current Chemistry is abbreviated Top. Curr. Chem. and is cited as a journal. Springer WWW home page: http://www.springer.de Visit the TCC home page at http:llink.springer.delseriesltccl or http:lllink.springer-ny.comlseriesltccl 2201-0430 NSSI ISBN 7-70144-045-3 Springer-Verlag Berlin Heidelberg New kroY Library of Congress Catalog Card Number 74-644622 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 thipsu blication or parts thereof is only permitted under the provisions of the German Copyright Law of September 9, ,5691 in its current version, andp ermission 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 http://www.springer.de © 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, 97084 Wfirzburg SPIN: 10863345 02/3020 ra - 4 5 3 2 0 - 1 Printed on acid-free paper Volume Editor Prof. Dr. Thomas Wirth Department of Chemistry Cardiff University CF 10 3TB Cardiff, United Kingdom E-maih [email protected] Editorial Board Prof. Dr. Armin de Meijere Prof. K.N. Houk Institut Organische ffir Chemie Department of Chemistry and Biochemistry der Georg-August-Universit/it University of California Tammannstrat]e 2 504 Avenue Hflgard 77073 G6ttingen, Germany soL Angeles, AC ,9851-42009 ASU l ameijer E-maih tteog-inu@ ed.negni :liam-E ude.alcu.mehc@kuoh Prof. Dr. Horst Kessler Prof. Jean-Marie Lehn Institut Organische Chemie ffir Institut de Chimie Mfinchen TU Universit~ de Strasbourg e~tartsgrebnethciL 4 1 rue Pascal, Blaise .P.B Z 8R/692 74758 Garching, Germany 80076 France Strasbourg Cedex, :liam-E ed.mut.hc@relssek E-maih rf.gbsarts-u.eimihc@nhel Prof. Steven .V Ley Prof. Stuart L. Schreiber Chemical University Laboratory Laboratories Chemical Road Lensfield Harvard University Cambridge 2BC ,WE1 Britain Great 21 Street Oxford E-maih ku.ca.mac.suc@OOOllvs Cambridge, AM ,2092-83120 ASU E-maih ude.dravrah.sirisls@sls Prof. Dr. Joachim Thiem Institut fiir Organische Chemie Prof. Barry M. Trost Universit/it Hamburg Department of Chemistry Martin-Luther-King-Platz 6 Stanford University 64102 Hamburg, Germany Stanford, AC ,0805-50349 ASU E-mail: ed.grubmah-inu.eimehc@meiht E-maih ude.drofnats.dnalel@tsortmb Prof. Dr. Fritz V6gtle Prof. Hisashi Yamamoto Kekul&Institut Organische Chemie ffir School of Engineering und Biochemie der ti~tisrevinU Bonn University Nagoya Gerhard-Domagk-Strat~e 1 Nagoya Chikusa, ,10-464 Japan 12135 Bonn, Germany E-maih pj.ca.u-ayogan.cc.ccun@a88954j .'liam-E ed.nnob-inu@eltgeov scipoT in Current Chemistry Also Available Electronically For all customers with a standing order for Topics in Current Chemistry we offer the electronic form via LINK free of charge. Please contact your librarian who can receive a password for free access to the full articles by registration at: http:l llink.springer.delorderslindex.htm If you do not have a standing order you can nevertheless browse through the table of contents of the volumes and the abstracts of each article at: http:l llink.springer.delseriesltcc http:/llink.springer-ny.comlseriesltcc There you will also find information about the Editorial Board - - Aims and Scope - Instructions for Authors ecaferP 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 condi- tions 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 morteh an five years ago. We felt that there a is need for an update. I am grateful to the distinguished scientists, who contributed, with their skill and expertise, thvea rious chapters of this volume. By emphasizing the developments in hyper- valent 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 stnetnoC Introduction and Aspects General T. Wirth . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . Reactivities, Properties and Structures M. Ochiai . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . Preparation of Hypervalent Iodine Compounds A. Varvoglis . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 69 C-C Bond Forming Reactions V.V. Zhdankin . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 99 C-Heteroatom-Bond Forming Reactions G. E Koser . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 137 Heteroatom-Heteroatom-Bond Forming Reactions G.E Koser . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 173 Oxidations and Rearrangements .T Wirth . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 185 Synthetic Applications Synthesis (Total and Natural Product Synthesis) H. Tohma, .Y Kita . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 209 Author Index Volumes 201-224 . . . . . . . . . . . . . . . . . . . . . . . 249 Subject Index . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 257 stnetnoC of Volume 208 muinelesonagrO yrtsimehC Modern stnempoleveD in cinagrO sisehtnyS Volume Editor: Thomas Wirth ISBN 3-540-66516-1 Introduction and GeneralA spects .T Wirth Electrophilic SeleniuSme,l enocyclizations 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 Introduction and General Aspects Thomas Wirth Department ofChemistry,CardiffUniversity,PO Box 912,CardiffCF10 3TB,UK E-mail:[email protected] Recent progress on hypervalent iodine chemistry is summarized in this book. Keywords. Hypervalent iodine chemistry Hypervalent iodine reagents were discovered a long time ago and (dichloro- iodo)benzene as the first member of this class was prepared by Willgerodt in 1886 [1].He was also the author ofthe first comprehensive book in this field in 1914 [2]. A growing interest in the chemistry with these compounds was observed about 60 years later, although some reviews on hypervalent iodine compounds were published as early as in the 1960s [3, 4]. Several reviews appeared between then and 1990 [5–17] and these are summarized in Table1. Recently many more reviews have been published on various parts of hyper- valent iodine chemistry [18–29] and several books [30–32] on this topic have appeared covering many aspects ofthese reagents. The purpose ofthis book is to address and summarize recent developments and synthetic applications in the field of hypervalent iodine chemistry.There- fore,emphasis is placed on the post 1990s literature with reference to earlier work where necessary and appropriate. The concept ofhypervalent molecules was established in 1969 [33].Molecules containing elements ofGroups 15–18 bearing more electrons than the octet in the valence shell are described as hypervalent molecules.Descriptions of such systems using molecular orbital theory led to the proposal of 3-center-4-elec- tron (3c–4e) bonds (hypervalent bonds) [34,35].Supported by computational work this concept is now generally accepted [36,37].Its application to iodanes is detailed at the beginning ofthe chapter Structures,Properties and Reactivities by M.Ochiai.The most common hypervalent iodine compounds are aryl-l3- iodanes (ArIL ) with a decet structure and pseudotrigonal bipyramidal geome- 2 tries and aryl-l5-iodanes (ArIL ) with a dodecet structure and square pyrami- 4 dal geometries.The nomenclature for these molecules is not satisfactory and several names for the same compound are often in use.Therefore,throughout this book various names and abbreviations for the hypervalent iodine reagents have been used by the authors as we have not applied the sometimes lengthy IUPAC names.As we have tried to outline general principles and synthetic con- cepts in this book, the chapter by M. Ochiai describes the theoretical back- ground ofhypervalent iodine reagents as well as giving examples oftheir reac- Topics in Current Chemistry,Vol.224 © Springer-Verlag Berlin Heidelberg 2003
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