Microwave Assisted Organic Synthesis

Edited by

Jason P. Tierney GlaxoSmithKline Harlow, UK Pelle Lidstr om Biotage AB Uppsala Sweden

c 2005 by Blackwell Publishing Ltd Editorial ofces: Blackwell Publishing Ltd, 9600 Garsington Road, Oxford OX4 2DQ, UK Tel: +44 (0)1865 776868 Blackwell Publishing Asia Pty Ltd, 550 Swanston Street, Carlton, Victoria 3053, Australia Tel: +61 (0)3 8359 1011 ISBN 1-4051-1560-2 Published in the USA and Canada (only) by CRC Press LLC, 2000 Corporate Blvd., N.W., Boca Raton, FL 33431, USA Orders from the USA and Canada (only) to CRC Press LLC USA and Canada only: ISBN 0-8493-2371-1 The right of the Author to be identied as the Author of this Work has been asserted in accordance with the Copyright, Designs and Patents Act 1988. All rights reserved. No part of this publication may be reproduced, stored in a retrieval system, or transmitted, in any form or by any means, electronic, mechanical, photocopying, recording or otherwise, except as permitted by the UK Copyright, Designs and Patents Act 1988, without the prior permission of the publisher. This book contains information obtained from authentic and highly regarded sources. Reprinted material is quoted with permission, and sources are indicated. Reasonable efforts have been made to publish reliable data and information, but the author and the publisher cannot assume responsibility for the validity of all materials or for the consequences of their use. Trademark notice: Product or corporate names may be trademarks or registered trademarks, and are used only for identication and explanation, without intent to infringe. First published 2005 Library of Congress Cataloging-in-Publication Data: A catalog record for this title is available from the Library of Congress British Library Cataloguing-in-Publication Data: A catalogue record for this title is available from the British Library Set in 10.5/12 pt Minion by TechBooks Printed and bound in India by Replika Press Pvt. Ltd, Kundli The publishers policy is to use permanent paper from mills that operate a sustainable forestry policy, and which has been manufactured from pulp processed using acid-free and elementary chlorine-free practices. Furthermore, the publisher ensures that the text paper and cover board used have met acceptable environmental accreditation standards. For further information on Blackwell Publishing, visit our website: www.blackwellpublishing.com

Contributors

D. Michael P. Mingos

Chemistry Department and St Edmund Hall, University of Oxford, Queens Lane, Oxford OX1 4AR, UK. michael.mingos@seh.ox.ac.uk Biolipox, Box 6280, SE-10234, Stockholm, Sweden. kristofer.olofsson@biolipox.com Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry, BMC, Uppsala University, Box 574, SE-75123 Uppsala, Sweden. mats@orgfarm.uu.se Laboratoire de Biotechnologie et Chimie Bioorganique associ e au CNRS, UFR Sciences Fondamentales et Sciences pour lIng enieur, B atiment Marie Curie, Universit e de La Rochelle, 17042 La Rochelle cedex, France. thierry. besson@univ-lr.fr Novartis Institute for Medical Sciences, 5 Gower Place, London WC1E 6BS, UK. christopher.brain@pharma. novartis.com The Oratory School, Woodcote, Reading, Berkshire RG8 0PJ, UK. T.Danks@oratory.co.uk Department of Chemistry, University of Surrey, Guildford, Surrey GU2 7XH, UK. G.Wagner@surrey.ac.uk Associate Professor, MedChemCon, Alands-V asterby, SE-74020 V ange, Sweden. jacob.westman@medchemcon.com RSC Wolfson Senior Research Scientist, Department of Chemistry, University of Cambridge, Lenseld Road, Cambridge CB2 1EW, UK. irb21@cam.ac.uk Department of Chemistry, University of Cambridge, Lenseld Road, Cambridge CB2 1EW, UK. leevz@bc.edu B01702 Prof. of Organic Chemistry, Department of Chemistry, University of Cambridge, Lenseld Road, Cambridge CB2 1EW, UK. svl1000@com.ac.uk Karl-Franzens-University Graz, Institute of Chemistry, Heinrichstrasse 28, A-8010 Graz, Austria. Alexander stadler@gmx.at

Kristofer Olofsson Mats Larhed

Thierry Besson

Christopher T. Brain

Timothy N. Danks Gabriele Wagner Jacob Westman Ian R. Baxendale

Dr. Ai-Lan Lee Prof. Steven V. Ley

Alexander Stadler

CONTRIBUTORS

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C. Oliver Kappe

Karl-Franzens-University Graz; Institute of Chemistry, Heinrichstrasse 28, A-8010 Graz, Austria. oliver.kappe@uni-graz.at Department of Medicinal Chemistry, Boehringer Ingelheim Pharmaceuticals, Inc., Research Development Center, 900 Ridgebury Rd, 06877-0368, Ridgeeld, CT, USA. csarko@rdg.boehringer-ingelheim.com Centre for Green Chemistry, Monash University, Clayton, Victoria, 3800, Australia. chris.strauss@sci.monash.edu.au CSIRO Molecular Science, Private Bag 10, Clayton South 3169, Victoria, Australia. Brett.Roberts@csiro.au

Christopher R. Sarko

Christopher R. Strauss Brett A. Roberts

Preface

Microwave-assisted organic chemistry has during the last years moved from being an obscurity in the laboratory environment to be an invaluable tool within chemistry research. Although the rst reports on microwave-assisted organic synthesis dates back as far as 1986, the breakthrough of the technique as a routine tool in synthesis has been slow. The main reason has been difculties in conquering the forces of the ame, i.e. there has been a lack of dedicated equipment available to perform chemistry using microwave irradiation. This lack of dedicated equipment led to the use of domestic appliances, leading to very unpredictable and sometimes devastating results. It also gave the technique an aura of black art. However, with the introduction of dedicated equipment, novel, interesting, reproducible chemistry has been and is continuously performed. In this book we have tried to assemble a selection of authors to shine light on the underlying principles of microwave dielectric heating, how this dielectric heating has been used in chemistry to give us microwave-assisted organic synthesis applied on a wide variety of reaction types as well as on how microwave-assisted organic synthesis has impacted the chemistry research within industry. These chapters have been written by some of the most prominent researchers of modern microwave-assisted organic synthesis and we hope that you will nd it both interesting and enlightening. Jason P. Tierney Pelle Lidstr om

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