Radicals in Synthesis I PDF
Preview Radicals in Synthesis I
263 Topics in Current Chemistry EditorialBoard: V.Balzani·A.deMeijere·K.N.Houk·H.Kessler·J.-M.Lehn S.V.Ley·S.L.Schreiber·J.Thiem·B.M.Trost·F.Vögtle H.Yamamoto TopicsinCurrentChemistry RecentlyPublishedandForthcoming Volumes SupramolecularChirality LowMolecularMassGelators VolumeEditors:Crego-Calama,M., Design,Self-Assembly,Function Reinhoudt,D.N. VolumeEditor:Fages,F. Vol.265,2006 Vol.256,2005 RadicalsinSynthesisII AnionSensing ComplexMolecules VolumeEditor:Stibor,I. VolumeEditor:Gansäuer,A. Vol.255,2005 Vol.264,2006 OrganicSolidStateReactions RadicalsinSynthesisI VolumeEditor:Toda,F. MethodsandMechanisms Vol.254,2005 VolumeEditor:Gansäuer,A. Vol.263,2006 DNABindersandRelatedSubjects VolumeEditors:Waring,M.J.,Chaires,J.B. MolecularMachines Vol.253,2005 VolumeEditor:Kelly,T.R. Vol.262,2006 ContrastAgentsIII VolumeEditor:Krause,W. ImmobilisationofDNAonChipsII Vol.252,2005 VolumeEditor:Wittmann,C. Vol.261,2005 ChalcogenocarboxylicAcidDerivatives VolumeEditor:Kato,S. 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Vol.247,2005 Radicals in Synthesis I MethodsandMechanisms Volume Editor: AndreasGansäuer Withcontributionsby A.Barchuk·F.Brebion·D.Crich·K.Daasbjerg·V.Darmency A.Gansäuer·M.Gerenkamp·S.Grimme·C.Mück-Lichtenfeld P.Renaud·M.P.Sibi·D.-H.Suk·H.Svith·J.Zimmerman·H.Zipse 123 TheseriesTopicsinCurrentChemistrypresentscriticalreviewsofthepresentandfuturetrendsin modernchemicalresearch.Thescopeofcoverageincludesallareasofchemicalscienceincluding theinterfaceswithrelateddisciplinessuchasbiology,medicineandmaterialsscience.Thegoalof eachthematic volumeistogivethenonspecialistreader,whether attheuniversityorin industry, acomprehensiveoverviewofanareawherenewinsightsareemergingthatareofinteresttoalarger scientificaudience. Asarule,contributionsarespeciallycommissioned.Theeditorsandpublisherswill,however,always bepleasedtoreceivesuggestionsandsupplementaryinformation.PapersareacceptedforTopicsin CurrentChemistryinEnglish. InreferencesTopicsinCurrentChemistryisabbreviatedTopCurrChemandiscitedasajournal. VisittheTCCcontentatspringerlink.com ISSN0340-1022 ISBN-103-540-31329-XSpringerBerlinHeidelbergNewYork ISBN-13978-3-540-31329-8SpringerBerlinHeidelbergNewYork DOI10.1007/11420187 Thisworkissubjecttocopyright.Allrightsarereserved,whetherthewholeorpartofthematerial isconcerned,specificallytherightsoftranslation,reprinting,reuseofillustrations,recitation,broad- casting,reproductiononmicrofilmorinanyotherway,andstorageindatabanks.Duplicationof thispublicationorpartsthereofispermittedonlyundertheprovisionsoftheGermanCopyrightLaw ofSeptember9,1965,initscurrentversion,andpermissionforusemustalwaysbeobtainedfrom Springer.ViolationsareliableforprosecutionundertheGermanCopyrightLaw. 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Coverdesign:Design&ProductionGmbH,Heidelberg TypesettingandProduction:LE-TEXJelonek,Schmidt&VöcklerGbR,Leipzig Printedonacid-freepaper 02/3100YL–543210 VolumeEditor Prof.Dr.AndreasGansäuer Kekulé-InstitutfürOrganische ChemieundBiochemie Gerhard-Domagk-Straße1 53121Bonn,Germany [email protected] EditorialBoard Prof.VincenzoBalzani Prof.Jean-MarieLehn DipartimentodiChimica„G.Ciamician“ ISIS UniversityofBologna 8,alléeGaspardMonge viaSelmi2 BP70028 40126Bologna,Italy 67083StrasbourgCedex,France [email protected] [email protected] Prof.Dr.ArmindeMeijere Prof.StevenV.Ley InstitutfürOrganischeChemie UniversityChemicalLaboratory derGeorg-August-Universität LensfieldRoad Tammanstr.2 CambridgeCB21EW 37077Göttingen,Germany GreatBritain [email protected] [email protected] Prof.Dr.KendallN.Houk Prof.StuartL.Schreiber UniversityofCalifornia ChemicalLaboratories DepartmentofChemistryand HarvardUniversity Biochemistry 12OxfordStreet 405HilgardAvenue Cambridge,MA02138-2902 LosAngeles,CA90024-1589 USA USA [email protected] [email protected] Prof.Dr.JoachimThiem Prof.Dr.HorstKessler InstitutfürOrganischeChemie InstitutfürOrganischeChemie UniversitätHamburg TUMünchen Martin-Luther-King-Platz6 Lichtenbergstraße4 20146Hamburg,Germany 86747Garching,Germany [email protected] [email protected] VI EditorialBoard Prof.BarryM.Trost Prof.Dr.HisashiYamamoto DepartmentofChemistry DepartmentofChemistry StanfordUniversity TheUniversityofChicago Stanford,CA94305-5080 5735SouthEllisAvenue USA Chicago,IL60637 [email protected] USA [email protected] Prof.Dr.F.Vögtle Kekulé-InstitutfürOrganischeChemie undBiochemie derUniversitätBonn Gerhard-Domagk-Str.1 53121Bonn,Germany [email protected] TopicsinCurrentChemistry AlsoAvailableElectronically ForallcustomerswhohaveastandingordertoTopicsinCurrentChemistry, weoffertheelectronicversionviaSpringerLinkfreeofcharge.Pleasecontact yourlibrarianwhocanreceiveapasswordorfreeaccesstothefullarticlesby registeringat: springerlink.com Ifyoudonothaveasubscription,youcanstillviewthetablesofcontentsofthe volumesandtheabstractofeacharticlebygoingtotheSpringerLinkHome- page,clickingon“BrowsebyOnlineLibraries”,then“ChemicalSciences”,and finallychooseTopicsinCurrentChemistry. Youwillfindinformationaboutthe – EditorialBoard – AimsandScope – InstructionsforAuthors – SampleContribution atspringer.comusingthesearchfunction. Preface “I didn’t think that radical chemistry could be so mild and selective,” is the nicer version of comments one often hears after seminars. What is the un- derlyingreasonforthemisconception?Probablythatradicaltransformations oftenseemcounterintuitive tothosebroughtupwithclassicalretrosynthetic schemes. As a result, the use of radicals is considered by many synthetic chemists as a last resort only to be used when other more traditionalmeth- odshave failed. Additionally, radicalreactions are usually regarded asbeing unselectiveandinvolvingtoxicreagents. This is, of course, false; such a conservative approach neglects the mild, selective,andoriginalsolutionsavailablethroughusingradicalchemistryfor demandingsyntheticproblems.Moreover,asolidphysicalorganicunderstand- ingofthemechanismbehindmostradicalreactionshasnowbeenestablished. This basis serves us well in predicting many results as well as in developing novelreactions.Inshort,radicalchemistryhasdevelopedwithamazingspeed fromalaboratorycuriosityintoanintegral,predictable,andhighlyproductive partoforganicchemistry.Thisaccountismeant tofurtherspreadthispoint ofview. The first volume (Methods and Mechanisms) concentrates on the mecha- nistic aspects of radical chemistry and the development of novel methods, while thesecond volume (Complex Molecules) focuses onthe use ofradicals in synthetic applications. While such traditional separation (novel methods are increasingly aimed at preparing complex molecules and the synthesis of complex molecules requires careful planning) may seem a little outdated at thebeginning ofthe21st century, itisnevertheless employed forthesake of convenience. The chapters, written by leading experts, provide state-of-the-art reviews ofexcitingandpertinenttopicsofcurrentresearchinradicalchemistry.These includeadiscussionofcomputeddataconcerningradicalstabilitiesandtheir evaluation,thesurprisingchemistryofradicalcations,modernconceptsand reagents for enantioselective radical chemistry, the mechanistic aspects of epoxideopeningviaelectrontransfer,theevolutionofecologicallybenignand efficient tin-free radical reactions, the attractive novel reagents and radical traps for unusual cyclizations, the exciting possibilities of xanthate derived radical processes, the emerging field of radical chemistry on solid supports, X Preface therecentdevelopmentofhighlyversatileradicaltandemreactions,themild and selective derivatization of amino acids and sugars through the use of radicals, and the increasing use of Cp TiCl-catalyzed and -mediated radical 2 reactionsinnaturalproductsynthesis. Of coursenotalloftheexciting recent developments inradicalchemistry canbecovered indepth in just twobooks.It isthereforeplanned toexpand thisseriesinthenearfuture. Ioffermyapologiestotheauthorsleftoutthis timeandaskthemtocontributenexttime! Hopefullythisbookwillmeetthechallengeofconvincingalargenumberof scientistsofthebenefitsofradicalchemistryandsparknoveldevelopmentsin thefieldsofnewradicalmethodologyandtheapplicationofradicalreactions inthesynthesisofcomplexmolecules. Bonn,February2006 AndreasGansäuer
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