Practical synthetic organic chemistry : reactions, principles, and techniques

870 Pages·2011·38.72 MB·English

by  Stéphane Caron

PRACTICAL SYNTHETIC
ORGANIC CHEMISTRY

PRACTICAL SYNTHETIC
ORGANIC CHEMISTRY
Reactions, Principles, and Techniques
Edited by
STE´PHANE CARON
Copyright 2011byJohnWiley&Sons,Inc.Allrightsreserved
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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