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Innovations in Organic Synthesis gems 1 LEY crepes Palladium Reagents and Catalysts Innovations in Organic Synthesis JIRO TSUJI Okayama University of Science, Okayama, Japan JOHN WILEY & SONS Chichester» New York - Brisbane - Toronto » Singapore Copyright © 1995 by John Wiley & Sons Lud, Baffins Lane, Chichester, ‘West Sussex POI9 IUD, England Telephone: National Chichester (01243) 779777 Intemational +44 1243 779777 All tights reserved, Reprinted with comrections, December 1996 Reprinted August 1997 and March 1998 ‘No part of this book may be reproduced by any means, or transmitted, or translated into a machine language without the written permission of the publisher Other Wiley Editorial Offices John Wiley & Sons, Inc., 605 Third Avenue, New York, NY 10158-0012, USA Jacaranda Wiley Lid, 33 Park Road. Milton, Queensland 4064, Australia John Wiley & Sons (Canada) Ltd, 22 Worcester Road, Rexdale, Ontario MW ILI, Canada John Wiley & Sons (Asia) Pte Ltd, 37 Jalan Pemimpin #05-04, Block B, Union Industrial Building, Singapore 2057 British Library Cataloguing in Publication Data A catalogue record for this book is available from the British Library ISBN 0 471 95483 7; 0.471 97202 9 (pbk) ‘Typeset in 10/12pt Times by Alden Multimedia Printed and bound in Great Britain by Biddles Ltd, Guildford and King’s Lynn This book is printed on acid-free paper responsibly manufactured froin sustainsibleforestation, For which at least wo trees are planted for each one used for paper production. Contents Preface Abbreviations 1 The Basic Chemistry of Organopalladium Compounds 1 Characteristic Features of Pd-Promoted or -Catalyzed Reactions 2 Palladium Compounds, Complexes, and Ligands Widely Used in Organic Synthesis 3 Fundamental Reactions of Pd Compounds 3.1 ‘Oxidative’ Addition Reaction 3.2 Insertion Reaction 3.3 Transmetallation Reaction 3.4 The Final Step of Pd-Promoted or -Catalyzed Reactions 3.4.1 Reductive Elimination Reaction 3.4.2 Elimination of -Hydrogen 3.5 How are Catalytic Reactions Possible? 4. References 2. Classification of the Reactions Involving Pd(11) Compounds and P4(0) Complexes in This Book 1 Stoichiometric and Catalytic Reactions 2 Stoichiometric Oxidative Reactions with Pd(I) Compounds in which Pd(II) is Reduced to Pd(0) Catalytic Reactions Mainly with Pd(0) Complexes The Characteristic Features of Ph—C Bonds References wee Oxidative Reactions with Pd(I1) Compounds Introduction. Reactions of Alkenes | Introduction Reaction with Water Re 3 xi xiii 19 ibs 21 21 2