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L-G-0003840151-0002367386.Pdf Handbook of Reagents for Organic Synthesis Catalyst Components for Coupling Reactions OTHER TITLES IN THIS COLLECTION Fluorine-Containing Reagents Edited by Leo A. Paquette ISBN 978 0 470 02177 4 Reagents for Direct Functionalization for C–H Bonds Edited by Philip L. Fuchs ISBN 0 470 01022 3 Reagents for Glycoside, Nucleotide, and Peptide Synthesis Edited by David Crich ISBN 0 470 02304 X Reagents for High-Throughput Solid-Phase and Solution-Phase Organic Synthesis Edited by Peter Wipf ISBN 0 470 86298 X Chiral Reagents for Asymmetric Synthesis Edited by Leo A. Paquette ISBN 0 470 85625 4 Activating Agents and Protecting Groups Edited by Anthony J. Pearson and William R. Roush ISBN 0 471 97927 9 Acidic and Basic Reagents Edited by Hans J. Reich and James H. Rigby ISBN 0 471 97925 2 Oxidizing and Reducing Agents Edited by Steven D. Burke and Rick L. Danheiser ISBN 0 471 97926 0 Reagents, Auxiliaries and Catalysts for C–C Bond Formation Edited by Robert M. Coates and Scott E. Denmark ISBN 0 471 97924 4 e-EROS For access to information on all the reagents covered in the Handbooks of Reagents for Organic Synthesis, and many more, subscribe to e-EROS on the Wiley Interscience website. A database is available with over 200 new entries and updates every year. It is fully searchable by structure, substructure and reaction type and allows sophisticated full text searches. http://www.mrw.interscience.wiley.com/eros/ Handbook of Reagents for Organic Synthesis Catalyst Components for Coupling Reactions Edited by Gary A. Molander University of Pennsylvania, Philadelphia, PA, USA Copyright # 2008 John Wiley & Sons Ltd, The Atrium, S outhern Gate, Chicheste r, West Sussex PO19 8SQ , Englan d Telephone (þ 44) 1243 779777 E-mail (for orders and customer servic e enquiries): cs-books @wiley.co.uk Visit our Home Page on www.wileyeurope.com or www.wiley.com 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, scanning or otherwise, except under the terms of the Copyright, Designs and Patents Act 1988 or under the terms of a licence issued by the Copyright Licensing Agency Ltd, 90 Tottenham Court Road, London W1T 4LP, UK, without the permission in writing of the Publisher. Requests to the Publisher should be addressed to the Permissions Department, John Wiley & Sons Ltd, The Atrium, Southern Gate, Chichester, West Sussex PO19 8SQ, England, or emailed to [email protected], or faxed to (+44) 1243 770620. This publication is designed to provide accurate and authoritative information in regard to the subject matter covered. It is sold on the understanding that the Publisher is not engaged in rendering professional services. If professional advice or other expert assistance is required, the services of a competent professional should be sought. Other Wiley Editorial Offices John Wiley & Sons Inc., 111 River Street, Hoboken, NJ 07030, USA Jossey-Bass, 989 Market Street, San Francisco, CA 94103-1741, USA Wiley-VCH Verlag GmbH, Boschstr. 12, D-69469 Weinheim, Germany John Wiley & Sons Australia Ltd, 33 Park Road, Milton, Queensland 4064, Australia John Wiley & Sons (Asia) Pte Ltd, 2 Clementi Loop #02-01, Jin Xing Distripark, Singapore 129809 John Wiley & Sons Canada Ltd, 6045 Freemont Boulevard, Mississauga, Ontario, Canada L5R 4J3 Wiley also publishes its books in a variety of electronic formats. Some content that appears in print may not be available in electronic books. Library of Congress Cataloging-in-Publication Data Handbook of reagents for organic synthesis. p. cm. Includes bibliographical references. Contents: [1] Reagents, auxiliaries, and catalysts for C–C bond formation/edited by Robert M. Coates and Scott E. Denmark [2] Oxidising and reducing agents/edited by Steven D. Burke and Riek L. Danheiser [3] Acidic and basic reagents/edited by Hans J. Reich and James H. Rigby [4] Activating agents and protecting groups/edited by Anthony J. Pearson and William R. Roush [5] Chiral Reagents for Asymmetric Synthesis/edited by Leo A. Paquette [6] Reagents for high- throughput solid-phase and solution-phase organic synthesis / edited by Peter Wipf [7] Reagents for glycoside, nucleotide and peptide synthesis / edited by David Crich [8] Reagents for direct functionalization of C–H bonds/edited by Philip L. Fuchs [9] Fluorine-Containing Reagents/edited by Leo A. Paquette [10] Catalyst Components for Coupling Reactions / edited by Gary A. Molander ISBN 0-471-97924-4 (v. 1) ISBN 0-471-97926-0 (v. 2) ISBN 0-471-97925-2 (v. 3) ISBN 0-471-97927-9 (v. 4) ISBN 0-470-85625-4 (v. 5) ISBN 0-470-86298-X (v. 6) ISBN 0-470-02304-X (v. 7) ISBN 0-470-01022-3 (v. 8) ISBN 978-0-470-02177-4 (v. 9) ISBN 978-0-470-51811-3 (v.10) 1. Chemical tests and reagents. 2. Organic compounds–Synthesis. QD77.H37 1999 98-53088 5470.2 dc 21 CIP British Library Cataloguing in Publication Data A catalogue record for this book is available from the British Library ISBN 13: 978-0-470-51811-3 (Hb) Typeset in 9½/11½ pt Times Roman by Thomson Press (India) Ltd., New Delhi. Printed and bound in Great Britain by Antony Rowe, Chippenham, Wiltshire This book is printed on acid-free paper responsibly manufactured from sustainable forestry in which at least two trees are planted for each one used for paper production. e-EROS Editorial Board Editor-in-Chief Leo A. Paquette The Ohio State University, Columbus, OH, USA Executive Editors David Crich Wayne State University, Detroit, MI, USA Philip L. Fuchs Purdue University, West Lafayette, IN, USA Gary Molander University of Pennsylvania, Philadelphia, PA, USA Contents Preface ix 1-Butyl-3-methylimidazolium Hexafluorophosphate ([Bmim]PF6) 182 Introduction xi (R,S)-CAMPHOS 189 Carbonyl(chloro)bis(triphenylphosphine)rhodium(I) 190 Recent Review Articles and Monographs 1 Chloro(1,5-cyclooctadiene)rhodium(I) Dimer 199 1-Adamantyl-di-tert-butylphosphine 5 Chlorotris(triphenylphosphine)rhodium(I) 206 Benzylchlorobis(triphenylphosphine)palladium(II) 7 Cobalt(II) Chloride 218 [1,10-Biphenyl]-2-yldicyclohexylphosphine 8 Copper 222 Bis(acetonitrile)[(1,2,5,6-)-1,5-cyclooctadiene]- Copper(II) Acetate 226 rhodium(1þ),tetrafluoroborate(1-) 12 Copper(II) Acetylacetonate 232 Bis(acetonitrile)dichloropalladium(II) 15 Copper(I) Bromide 235 Bis(allyl)di--chlorodipalladium 31 Copper Bronze 242 (R,R)-1,2-Bis(aminocarbonylphenyl-20- Copper(II) Chloride 243 diphenylphosphino)cyclohexane 54 Copper(I) Chloride-Oxygen 250 Bis(benzonitrile)dibromopalladium(II) 59 Copper(II) Hydroxide 264 Bis(benzonitrile)dichloropalladium(II) 60 Copper(I) Iodide 264 Bis(bicyclo[2.2.1]hepta-2,5-diene)dichlorodirhodium 84 Copper(I) Iodide–Potassium Naphthalenide 275 Bis[(1R)-[1,10-binaphthalene]-2,20-diylbis[diphenyl- Copper(I) Iodide–Triethyl Phosphite 275 phosphine-P]]di--hydroxydirhodium 88 Copper(I) Oxide 276 Bis[1,2-bis(diphenylphosphino)ethane]palladium(0) 90 Copper(I) Trifluoromethanesulfonate 281 [[2,6-Bis[[(bis(1-methylethyl)phosphino-P]methyl]-3,5 [(1R,2R,3S,4S)-1,2,3,4-Cyclopentanetetrakis(methylene)]- dimethylphenyl]methyl-C]trifluoroacetato-O)palladium 91 tetrakis[diphenyl]phosphine 303 Bis[(1,2,5,6-)-1,5-cyclooctadiene]di--hydroxydirhodium 92 Diacetatobis(tri-o-tolylphosphine)palladium(II) 307 Bis[(1,2,5,6-)-1,5-cyclooctadiene]di--methoxydirhodium 94 Dibromobis(triphenylphosphine)nickel(II) 307 Bis(1,5-cyclooctadiene)nickel(0) 95 Dibromobis(triphenylphosphine)palladium(II) 309 Bis[(1,2,5,6-)-1,5-cyclooctadiene] rhodium(1þ), 2-(Di-tert-butylphosphino)biphenyl 310 Hexafluoroantimonate(1À) 114 Dicarbonyl(acetylacetonato) rhodium(I) 314 Bis(dibenzylideneacetone)palladium(0) 118 Dichloro[1,4-bis(diphenylphosphino)butane]nickel(II) 316 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydroimidazol- Dichloro[1,4-bis(diphenylphosphino)butane]palladium(II) 318 2-ylidene 124 Dichloro[1,2-bis(diphenylphosphino)ethane]palladium(II) 320 1,3-Bis(2,6-diisopropylphenyl)-imidazol-2-ylidene 126 Dichloro[1,10-bis(diphenylphosphino)ferrocene]- Bis(1,1-dimethylethyl)[20,40,60-tris(1-methylethyl)[1,10- palladium(II) 321 biphenyl]-2-yl]phosphine and Dicyclohexyl[20,40,60-tris Dichlorobis(tricyclohexylphosphine)palladium 322 (1-methylethyl)[1,10-biphenyl]-2-yl]phosphine 127 Dichlorobis(triphenylphosphine)nickel(II) 326 (R)- & (S)-2,20-Bis(diphenylphosphino)-1,10-binaphthyl 130 Dichlorobis(triphenylphosphine)palladium(II) 332 1,4-Bis(diphenylphosphino)butane 141 Dichlorobis(tri-o-tolylphosphine)palladium(II) 343 (2R,3R)-2,3-Bis(diphenylphosphino)butane 142 Dichloro[2,3-O-isopropylidene-2,3-dihydroxy-1,4-bis- 1,2-Bis(diphenylphosphino)ethane 144 (diphenylphosphino)butane]palladium(II) 345 1,10-Bis(diphenylphosphino)ferrocene 146 Dicyclohexyl(20,60-dimethoxy[1,10-biphenyl]-2-yl)- Bis[2-(diphenylphosphino)phenyl]ether (DPE-phos) 155 phosphine (S-Phos) 346 1,3-Bis(diphenylphosphino)propane 161 2-Dicyclohexylphosphino-20-(N,N-dimethylamino)- Bis(2-ethene)(2,4-pentanedionato-O,O0) rhodium 163 biphenyl 348 Bis(triphenylphosphine)[1,2-bis(diphenylphosphino)- (R)-1-[(1R)-1-(Dicyclohexylphosphino)ethyl]-2- ethane]palladium(0) 165 (diphenylphosphino)-ferrocene, (2S)-1-[(1R)-1- Bis(triphenylphosphine)nickel(0) 167 (Dicyclohexylphosphino)ethyl]-2-(diphenylphosphino)- Bis(triphenylphosphine)palladium(II) acetate 168 ferrocene, (Josiphos) 353 Bis[tri(o-tolyl)phosphine]palladium 173 2-(20-Dicyclohexylphosphinophenyl)-2-methyl- Bromo(o-tolyl)bis(triethylphosphine)nickel(II) 182 1,3-dioxolane 364 viii CONTENTS 1-(4,5-Dihydro-4-phenyl-2-oxazolyl)-2-(diphenyl- Palladium–Graphite 502 phosphino) ferrocene 365
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