Compendium of Organic Synthetic Methods -Volume 12 PDF
Preview Compendium of Organic Synthetic Methods -Volume 12
Compendium of Organic Synthetic Methods Volume 12 MICHAEL B. SMITH Department of Chemistry The University of Connecticut Storrs, Connecticut @3 WILEY A JOHN WILEY & SONS, INC., PUBLICATION Copyright 02 009 by John Wiley & Sons, Inc. All rights reserved Published by John Wiley & Sons, Inc., Hoboken, New Jersey. Published simultaneously in Canada. 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 as permitted under Section 107 or 108 of the 1976 United States Copyright Act, without either the prior written permission of the Publisher, or authorization through payment of the appropriate per-copy fee to the Copyright Clearance Center, Inc., 222 Rosewood Drive, Danvers, MA 01923, (978) 750-8400, fax (978) 646-8600, or on the web at www.copyright.com. Requests to the Publisher for permission should be addressed to the Permissions Department, John Wiley & Sons, Inc., 11 1 River Street, Hoboken, NJ 07030, (201) 748-601 1, fax (201) 748-6008 or online at http://www.wiley,com/go/permission. Limit of LiabilityDisclaimer of Warranty: While the publisher and author have used their best efforts in preparing this book, they make no representations or warranties with respect to the accuracy or completeness of the contents of this book and specifically disclaim any implied warranties of merchantability or fitness for a particular purpose. No warranty may be created or extended by sales representatives or written sales materials. The advice and strategies contained herein may not be suitable for your situation. You should consult with a professional where appropriate. Neither the publisher nor author shall be liable for any loss of profit or any other commercial damages, including but not limited to special, incidental, consequential, or other damages. For general information on our other products and services or for technical support, please contact our Customer Care Department within the U.S. at (800) 762-2974, outside the U.S. at (317) 572-3993 or fax (317) 572-4002. Wiley also publishes its books in a variety of electronic formats. Some content that appears in print may not be available in electronic format. For information about Wiley products, visit our web site at www.wiley.com. Library of Congress Cataloging Card Number: 71-162800 ISBN 978-0-471-44530-2 Printed in the United States of America. 1 0 9 8 7 6 5 4 3 2 1 CONTENTS vii Preface ix Abbreviations ... Index, Monofunctional Compounds Xlll xiv Index, Difunctional Compounds Introduction XV 1 1 Preparation of Alkynes 9 2 Preparation of Acid Derivatives 17 3 Preparation of Alcohols 51 4 Preparation of Aldehydes 5 Preparation of Alkyls, Methylenes, and Aryls 67 151 6 Preparation of Amides 177 7 Preparation of Amines 209 8 Preparation of Esters 9 Preparation of Ethers, Epoxides, and Thioethers 227 10 Preparation of Halides and Sulfonates 245 11 Preparation of Hydrides 253 259 12 Preparation of Ketones 283 13 Preparation of Nitriles 14 Preparation of Alkenes 289 15 Preparation of Oxides 307 317 16 Preparation of Difunctional Compounds Author Index 507 V PREFACE Since the original volume in this series by Ian and Shuyen Harrison, the goal of the Compendi- um of Organic Synthetic Methods has been to facilitate the search for functional group transfor- mations in the original literature of Organic chemistry. In Volume 2, difunctional compounds were added, and this compilation was continued by Louis Hegedus and Leroy Wade for Volume 3 of the series. Professor Wade became the author for Volume and continued with Volume 5. I 4 began editing the series with Volume 6, where I introduced an author index for the first time and added a new chapter (Chapter 15, Oxides). Volume 7 introduced Sections 378 (Oxides-Alkynes) through Section 390 (Oxides-Oxides). The Compendium is a handy desktop reference that re- mains a valuable tool to the working organic chemist, allowing a quick check of the literature. Even in the era of powerful computer searching, the Compendium allows one to "browse" for new reactions and transformations that may be of interest in a rapid and logical manner. The body of Organic chemistry literature is very large and the Compendium is a focused and highly representative survey of the literature, and is offered in that context. Compendium of Organic Synthetic Methods, Volume 12 contains both functional group trans- formations and carbon-carbon bond-forming reactions from the literature appearing in the years 2002,2003, and 2004. The classification schemes used for Volumes 6-1 1 have been continued. Difunctional compounds appear in Chapter 16. The experienced user of the Compendium will require no special instructions for the use of Volume 12. Author citations and the Author Index have been continued as in Volumes 6-1 1. Every effort has been made to keep the manuscript error-free. Where there are errors, I take full responsibility. If there are questions or comments, the reader is encouraged to contact me directly at the address, phone, fax, or email given below. As I have throughout my writing career, I thank my wife, Sarah, and my son, Steven, for their encouragement and support during this work. I also thank Dr. Darla Henderson, Michael Forster, Jonathan Rose, Lauren Hilger, Rebekah Amos, and Angioline Loredo of Wiley for their help in the publication of this volume, MICHAEBL. SMITH Department of Chemistry, University of Connecticut 55 N. Eagleville Road Storrs. Connecticut 06269-3060 Voice phone: (860)-486-2881 Fax: (860)-486-2981 Email: [email protected] Storrs, Connecticut December 2008 vii ABBREVIATIONS Ac Acetyl acac Acety lacetonate AIBN azobis-isobutyronitde Aqueous 9-Borabicyclo[3.3.l]nonylboryl 9-BBN 9-Borabicyclo[3.3. llnonane BER Borohydride exchange resin BINAP 2R, 3S-2,2'-bis-( dipheny1phosphino)- 1,1' -binaphthyl Bmim 1- butyl-3-methylimidazolium Bn benzyl BOC tert-Butoxycarbonyl bPY (BiPY) 2,T-Bipyridyl Bu n-Butyl Bz Benzoyl "C Temperature in degrees Celsius CAM Carboxamidomethyl CAN Ceric ammonium nitrate (NH)2Ce(N03)6 C- Cyclo- cat. Catalytic \I b OCyPh Cbz Carbobenzyloxy Chirald 2S,3R-(+)-4-Dimethylamin1o,-2 -diphenyl-3-methylbutan-2-01 COD 1,5-Cyclooctadienyl COT 1,3,5-Cyclooctatrienyl CP Cyclopentadienyl CSA Camphorsulfonic acid CTAB Cetyltrimethylammonium bromide C 16H33NMe3+ Br- 0 4 CY (c-C6H11) Cyclohexyl DABCO 1,4-Diazabicylco[ 2 .2.21o ctane dba Dibenzylidene acetone DBE 1,2-Dibromoethane BrCH2CH2Br DBN 1,5-Diazabicyclo[4.3.O]non-5-ene DBU 1,8-Diazabicyclo[5.4.O]undec-7-ene DCC 1,3- Dicy clohexylcarbodiimide C-C&11-N=C=N-C-C6H11 ix Abbreviations X DCE 1,2-Dichloroethane DCM Dichloromethane DDQ 2,3-Dichloro-5,6-dicyano1-, 4-benzoquinone % de % Diastereomeric excess DEA Diethy lamine DEAD Diethylazodicarboxylate Dibal-H Diisobutylaluminum hydride Diphos (dppe) 1,2-bis-(Diphenylphosphino)ethane Diphos-4 (dppb) 1,4-bis-(Diphenylphosphino)butane DMA Dimethylacetamide DMAP 4-Dimethylaminopyridine DME Dimethoxy ethane MeOCH2CH20Me 13 DMF N,N’-Dimethylformamide HA N(CH3)2 dmP bis- [ 1,3-Di(p-methoxyphenyl)1-, 3-propanedionato] dPm Dipivaloylmethanato dPPb 1,4-bis-(Diphenylphosphino)butane Ph2P(CH2) 4PPh2 Ph2PCH2CH2PPh2 dPPe 1,2-bis-(Diphenylphosphino)ethane dPPf bis-(Dipheny1phosphino)ferrocene Ph2P(CH2) 3PPh2 dPPP 1,3-bis-(Diphenylphosphino)propane dvb Diviny lbenzene e- Electrolysis % ee % Enantiomeric excess EDA Ethy lenediamine H~NCH~CH~NHZ EDTA Ethylenediaminetetraacetic acid EE 1- Ethoxyethoxy EtO(Me)CHO- Et Ethyl -CH2CH3 FMN Flavin mononucleotide fod tris-(6,6,7,7,8,8,8)-Heptafluoro-2,2-dimethyl-3,5-octanedionate FP Cyclopentadienyl-bis-carbonylir on FVP Flash Vacuum Pyrolysis h Hour (hours) hv Irradiation with light 1,5-HD 15Hexadienyl HMPA Hexamethy lphosphoramide (Me2N)3P=O HMPT Hexamethylphosphorus triamide (Me2N)3P iPr Isopropyl -CH(CH3)2 LICA (LIPCA) Lithium cyclohexylisopropylamide LDA Lithium diisopropylamide LiN(iPr)2 LHMDS Lithium hexamethyldisilazide LiN(SiMe2)z LTMP Lithium 2,2,6,6-tetramethylpiperidide MABR Methylaluminum bis-(4-bromo-2,6-di-tert-butylphenoxide) MAD bis-( 2,6-di- te rt-b uty l-4-methy1phenoxy)methyl aluminum mCPBA meta-Chloroperoxybenzoic acid Me Methyl -CH3 MEM P-Methoxyethoxymethyl MeOCH2CH20CH2- Abbreviations xi Mes Mesityl 2,4,6-tri-Me-CgH2 MOM Methoxymethyl MeOCH2- Ms Methanesulfonyl CH3S02- MS Molecular Sieves (3 or ,4 A) MTM Methylthiomethyl CH3SCH2- NAD Nicotinamide adenine dinucleotide NADP Sodium triphosphopyridine nucleotide Napth Naphthyl (C10Hd NBD Norbornadiene NBS N-Bromosuccinimide NCS N-Chlorosuccinimide Ni(R) Raney nickel NIS N-Iodosuccinimide NMP N-Methyl-2-p yrrolidinone Oxone 2 KHSOS*KHSO~*K~SO~ Polymeric backbone PCC Pyridinium chlorochromate PDC Pyridinium dichromate PEG Polyethylene glycol Ph Phenyl PhH Benzene PhMe To1 u en e Phth Phthaloyl pic 2-Pyridinecarboxylate Pip Piperidino PMP 4-Methoxyphenyl Pr n-Propyl PY Pyridine quant. Quantitative yield Red-A1 [ (MeOCH2CH20)2AlHz]Na S-BU sec-Butyl CH3CH2CH(CH3) s-BuLi sec-Butyllithium CH&H2CH(Li)CH3 Siamyl Diisoamyl (CH3) 2CHCH(CH3)- TADDOL 1,3-dioxolane a,a,a’,a’-tetraaryl-4,5-dimethoxy- TASF difluorotrimethyl silicate tris-(Diethy1amino)sulfonium TBAF Tetrabutylammonium fluoride n-Bu4N+ F TBDMS tert-Butyldimethy lsilyl t-BuMe2Si TBDPS tert-Butyldiphenylsilyl t-BuPh2Si TBHP (t-BuOOH) tert-Butylhydroperoxide Me3 C 00 H t-Bu tert-Butyl -C(CH3)3 TEBA Triethylbenzy lammonium Bn(Et)3N+ TEMPO Tetramethylpiperdinyloxy free radical xii Abbreviations TFA Trifluoroacetic acid TFAA Trifluoroacetic anhydride Tf (OTf) Triflate THF Tetrahydrofuran THP Tetrahy dropyran TMEDA Tetramethylethylenediamine TMG 1,1,3,3-Tetramethylguanidine TMP 2,2,6,6-Tetramethylpiperidine TMS Triniethy lsilyl -Si(CH3)3 TPAP tetra-n-Propylammonium perruthenate To1 Tolyl Tr Trityl TRIS Triisopropylphenylsulfonyl Ts(Tos) Tosyl = p-Toluenesulfonyl XC Chiral auxiliary INDEX, MONOFUNCTIONAL COMPOUNDS Sections-heavy type Pages-light type ' 1 ' 16 31 46 61 76 Alkynes -_ 9 ~ 17 ~~ 51 ~, 67- t15-1 Carboxylic acid derivatives Alcohols, phenols - ' 1 Alakryyllss, mAeltdheyhleyndeess, .45 1 ........ 21110091 +~1, . 33314518 i~!~1 -4596 -~1 ..-.6767..1245 +~!, 78110955 53 9147 9 11112211016709 I11 112223325014 ~~ 212144346709 iI1I 221155554445 ~1 221166675690 1'Ij 218834 1229008 11 231085 Amides 181 ~ 211171 ~ ~ 216771 218846 ~ ~ 231068 Amines 182 I211172 1 1 1 216772 ' 1! 230187 Esters Ethers, epxoides 1 1 i 1 Halides, sulfonates 16 0 1 2153 4306 1~ 5558 i~ 7709 1 8156 6 110902 I! 212115 II 1233034 I - 2144_75- 215650 1 217705 II 218950 ~ 230050 1 232101 Hydrides (RH) Ketones Nitriles i3 4453 ~1 5598 I1 7993 ' ;;o ..... ~ ...... 4 1. .... Alkenes Miscellaneous 1 PROTECTION 1 Blanks in the table correspond to sections for which no additional Sect. Pg. examples were found in the literature Carboxylic acids 30A 15 Alcohols, thiols 45A 46 Aldehydes 60A 61 hides 90A 176 Amines 105A 206 Ketones 180A 279 ... Xlll
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