Practical synthetic organic chemistry : reactions, principles, and techniques PDF
Preview Practical synthetic organic chemistry : reactions, principles, and techniques
PRACTICAL SYNTHETIC ORGANIC CHEMISTRY PRACTICAL SYNTHETIC ORGANIC CHEMISTRY Reactions, Principles, and Techniques Edited by STE´PHANE CARON Copyright 2011byJohnWiley&Sons,Inc.Allrightsreserved PublishedbyJohnWiley&Sons,Inc.,Hoboken,NewJersey PublishedsimultaneouslyinCanada Nopartofthispublicationmaybereproduced,storedinaretrievalsystem,ortransmittedinanyformorbyany means,electronic,mechanical,photocopying,recording,scanning,orotherwise,exceptaspermittedunder Sections107or108ofthe1976UnitedStatesCopyrightAct,withouteitherthepriorwrittenpermissionof thePublisher,orauthorizationthroughpaymentoftheappropriateper-copyfeetotheCopyrightClearance Center,Inc.,222RosewoodDrive,Danvers,MA01923,(978)750-8400,fax(978)750-4470,oronthewebat www.copyright.com. Requests to the Publisher for permission should be addressed to the Permissions Department,JohnWiley&Sons,Inc.,111RiverStreet,Hoboken,NJ07030,(201)748-6011,fax(201)748-6008, or online at http://www.wiley.com/go/permission. LimitofLiability/DisclaimerofWarranty:Whilethepublisherandauthorhaveusedtheirbesteffortsinpreparing thisbook,theymakenorepresentationsorwarrantieswithrespecttotheaccuracyorcompletenessofthecontents ofthisbookandspecificallydisclaimanyimpliedwarrantiesofmerchantabilityorfitnessforaparticularpurpose. Nowarrantymaybecreatedorextendedbysalesrepresentativesorwrittensalesmaterials.Theadviceand strategiescontainedhereinmaynotbesuitableforyoursituation.Youshouldconsultwithaprofessionalwhere appropriate.Neitherthepublishernorauthorshallbeliableforanylossofprofitoranyothercommercial damages,includingbutnotlimitedtospecial,incidental,consequential,orotherdamages. Forgeneralinformationonourotherproductsandservicesorfortechnicalsupport,pleasecontact ourCustomerCareDepartmentwithintheUn itedStatesat(800)762-2974,outsidetheUnitedStates at(317)572-3993orfax(317)572-4002. Wileyalsopublishesitsbooksinavarietyofelectronicformats.Somecontentthatappearsinprintmay notbeavailableinelectronicformats.FormoreinformationaboutWileyproducts,visitourwebsite at www.wiley.com. LibraryofCongressCataloging-in-PublicationData: Practicalsyntheticorganicchemistry:reactions,principles,andtechniques/editedbySt(cid:1)ephaneCaron. p.cm. Includesindex. ISBN978-0-470-03733-1(pbk.) 1.Organiccompounds–Synthesis. I.Caron,St(cid:1)ephane. QD262.P6882011 547’.2–dc22 2011008293 PrintedintheUnitedStatesofAmerica oBooKISBN:978-1-118-09355-9 ePDFISBN: 978-1-118-09357-3 ePubISBN: 978-1-118-09356-6 10 9 8 7 6 5 4 3 2 1 CONTENTS Foreword vii Preface ix Contributors xi 1 AliphaticNucleophilicSubstitution 1 JadeD.Nelson 2 AdditiontoCarbon–Heteroatom MultipleBonds 73 RajappaVaidyanathanandCarrieBrockwayWager 3 AdditiontoCarbon–CarbonMultipleBonds 167 JohnA.Ragan 4 NucleophilicAromaticSubstitution 237 Ste´phaneCaronandArunGhosh 5 ElectrophilicAromaticSubstitution 255 Ste´phaneCaron 6 SelectedMetal-MediatedCross-CouplingReactions 279 Ste´phaneCaron,ArunGhosh,SallyGutRuggeri,NathanD.Ide,JadeD.Nelson, andJohnA.Ragan 7 Rearrangements 341 DavidH.B.Ripin 8 Eliminations 383 SallyGutRuggeri v vi CONTENTS 9 Reductions 419 SallyGutRuggeri,Ste´phaneCaron,PascalDube´,NathanD.Ide, KristinE.Price,JohnA.Ragan,andShuYu 10 Oxidations 493 DavidH.BrownRipin 11 SelectedFreeRadicalReactions 557 NathanD.Ide 12 Synthesisof“Nucleophilic”OrganometallicReagents 575 DavidH.BrownRipin 13 SynthesisofCommonAromaticHeterocycles 609 Ste´phaneCaron 14 AccesstoChirality 649 RobertW.Dugger 15 SyntheticRouteDevelopmentofSelectedContemporary PharmaceuticalDrugs 661 Ste´phaneCaron 16 GreenChemistry 683 JuanC.Colberg 17 NamingCarbocyclesandHeterocycles 703 HeatherN.FrostandDavidH.BrownRipin 18 pKa 771 DavidH.BrownRipin 19 GeneralSolventProperties 805 Ste´phaneCaron 20 PracticalChemistryConcepts:TipsforthePracticingChemistor ThingsTheyDon’tTeachYouinSchool 819 SallyGutRuggeri FunctionalGroupInterconversionIndex 837 Index 845 FOREWORD Whileallpractitionersintheartrecognizethatsyntheticorganicchemistryservessociety,it isnotalwaysappreciatedtheotherwayaround;namelythatsocietydoesnotassociatethe phenomenal rewards that are derived from our ability to assemble complex functional molecules. Indeed,theachievementsofthepharmaceutical industryareunderpinnedby moleculardesignandsynthesisofvirtuallyallthehealingdrugsubstancesthatarecurrently onthemarket,whichbenefitmankindandcurehumandiseases. Thereis,inmyview,nothingnoblerthanthisworthwhiletask. However,synthesisofthe complexfunctionalarchitecturesisnotatrivialorroutineprocess.Thisisalwaysmademore difficult on scaling up of the chemistries to comply with current standards of safety, robustness, costs, quality, and environmental impact. I, therefore, very much welcome this new textbook, Practical Synthetic Organic Chemistry: Reactions, Principles, and Techniques, which gives us an inspiring and pragmatic glimpse at the most commonly usedandeffectivesynthesisproceduresonscale. Thisuniquetextbookhasbeenwrittenby experts in the field and provides an insight and critique of the key effectivemethods for molecularassembly.Itwillbeagreatstartingpointforanyonedevelopingtheircareerinthis worthyindustry. The organization and chapter titles reflect a refreshing approach to explaining a complicated science covering all the major bond construction methods and functional controlelementsnecessaryformodernsyntheticplanningandexecution. Theauthorshaveincorporatedchaptersonimportanttopicssuchastheeffectivenessof rearrangementprocesses,radicalreactions,accesstochirality,andgreenchemistry,which are not captured as a group in more traditional texts. Furthermore, the educational component of this book highlighting nomenclature, pKa knowledge, solvent properties, andtipsofthetradefromthepracticingchemistagainaddsvalueinprovidingafeastof information that otherwise is dispersed over many sources or is simply locked up in the personaldatabaseofknowledgeofthoseexperiencedintheart. vii viii FOREWORD Thecreativespiritofthisareaofscienceinbringingnewfunctional molecules inour worldforthefirsttimeforthebettermentofusallisenduringandwillcontinuetoseednew discoveriesformanyyearstocome. STEVEN V. LEY Cambridge,UK 2011
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