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Solid-phase organik syntheses - Burdges K.

Solid-phase organik syntheses

Author: Burdges K.
Publishers: John Wiley & Sons
Year of publication: 2000
Number of pages: 283
ISBN 0-471-22824-9
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Download: phaseorganicsynthesis2000.pdf

Solid-Phase Organic Synthesis. Edited by Kevin Burgess Copyright 2000 John Wiley & Sons, Inc. ISBNs: 0-471-31825-6 (Hardback); 0-471-22824-9 (Electronic)
SOLID-PHASE ORGANIC SYNTHESIS
SOLID-PHASE ORGANIC SYNTHESIS
Edited by
KEVIN BURGESS
Texas A & M University College Station, Texas
WILEY-INTERSCIENCE
A John Wiley & Sons, Inc., Publication
New York / Chichester / Weinheim / Brisbane / Singapore / Toronto
Designations used by companies to distinguish their products are often claimed as trademarks. In all instances where John Wiley & Sons, Inc., is aware of a claim, the product names appear in initial capital or ALL CAPITAL LETTERS. Readers, however, should contact the appropriate companies for more complete information regarding trademarks and registration.
Copyright 2000 by John Wiley & Sons, Inc. 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 or mechanical, including uploading, downloading, printing, decompiling, recording or otherwise, except as permitted under Sections 107 or 108 of the 1976 United States Copyright Act, without the prior written permission of the Publisher. Requests to the Publisher for permission should be addressed to the Permissions Department, John Wiley & Sons, Inc., 605 Third Avenue, New York, NY 10158-0012, (212) 850-6011, fax (212) 850-6008,
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ISBN 0-471-22824-9
This title is also available in print as ISBN 0-471-31825-6.
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Vi CONTENTS
2.1. Introduction / 25
2.2. Heck Reaction / 27
2.3. Stille Reaction / 45
2.4. Suzuki Reaction / 48
2.5. Miscellaneous Reactions / 67
2.6. Concluding Remarks /71 References /71
3 BENZOFUSED HETEROCYCLES VIA SOLID-PHASE Sa/AR REACTIONS
Matthias K. Schwarz and Mark A. Gallop
(i) SwAr
aryl halide --------> ~ benzofused heterocycle
(ii) cyclize
3.1. Introduction /81
3.2. Formation of [6,7]- and [6,8]-Fused Systems / 84
3.3. Formation of [6,6]-Fused Systems / 97
3.4. Formation of [6,5]-Fused Systems / 105
3.5. Conclusions and Outlook / 108 References /111
SOLID-PHASE SYNTHESIS OF SEQUENCE-SPECIFIC PHENYLACETYLENE OLIGOMERS
Jeffrey S. Moore, David J. Hill, and Matthew J. Mio

n*_nr2
N
(i) Mel (ii) 1-alkyne/ couple
(iii) interconvert SP functionality (iv) repeat
4.1. Introduction / 119
4.2. Strategies /120
4.3. Synthetic Tactics / 122
4.4. Illustrative Applications /128
4.5. Scope and Limitations / 138
4.6. Conclusion / 140
CONTENTS Vii
4.7. Representative Procedures /140 References / 144
5 POLYMER-ASSISTED SOLUTION-PHASE METHODS
FOR CHEMICAL LIBRARY SYNTHESIS 149
Daniel L. Flynn, Rajesh V. Devraj, and John J. Parlow
intermediate product
+ -----------------> +
^capture group captured byproduct
oapiui e yi uup
5.1. Introduction / 149
5.2. Reactant Sequestration / 152
5.3. Byproduct Sequestration / 156
5.4. Solution-Phase Derivatization to Facilitate Polymer-Assisted Sequestration / 157
5.5. Soluble Bifunctional Reagents /160
5.6. Polymer-Supported Substrates /162
5.7. Polymer-Supported Reagents / 165
5.8. Polymer-Supported Catalysts / 168
5.9. Polymers for Reaction Quenching/Workup / 173
5.10. Combinations of Solid- and Solution-Phase Techniques in Organic Synthesis / 175
5.11. Multistep/One-Chamber Solution-Phase Synthesis /182
5.12. Polymer-Assisted Technologies in Multistep Solution-Phase Syntheses /183
5.13. Conclusion /187 References /188
6 SOLID-PHASE ORGANIC SYNTHESIS ON RADIATION-GRAFTED POLYMER SURFACES: APPLICATION OF SYNPHASE CROWNS TO MULTIPLE PARALLEL SYNTHESES 195
Ian W. James, Geoffrey Wickham, Nicholas J. Ede, and Andrew M. Bray
or intermediate - product pin pin
viii CONTENTS
6.1. Multiple Parallel Syntheses of Individual Compounds / 195
6.2. Synthetic Applications of Synphase Crowns / 200
6.3. Linker Development Using Synphase Crowns / 208
6.4. Tagging Methods for Identifying Individual Crowns /211
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