44 Topics in Organometallic Chemistry Editorial Board: M. Beller J. M. Brown P. H. Dixneuf l l A. Fu¨rstner L. Gooßen L. S. Hegedus l l P. Hofmann T. Ikariya L. A. Oro Q.-L. Zhou l l l Topics in Organometallic Chemistry Recently Published Volumes Hydrofunctionalization IronCatalysis–Fundamentalsand VolumeEditors:ValentineP.Ananikov, Applications MasatoTanaka VolumeEditor:B.Plietker Vol.43,2013 Vol.33,2011 OrganometallicsasCatalysts MedicinalOrganometallicChemistry intheFineChemicalIndustry VolumeEditors:G.Jaouen,N.Metzler-Nolte VolumeEditors:MatthiasBeller, Vol.32,2010 Hans-UlrichBlaser C-XBondFormation Vol.42,2012 VolumeEditor:A.Vigalok Vol.31,2010 ModernOrganoaluminumReagents: Preparation,Structure,ReactivityandUse TransitionMetalComplexesofNeutral VolumeEditors:SimonWoodward, h1-CarbonLigands SamuelDagorne VolumeEditors:R.Chauvin,Y.Canac Vol.41,2012 Vol.30,2010 OrganometallicPincerChemistry PhotophysicsofOrganometallics VolumeEditors:GerardvanKoten, VolumeEditor:A.J.Lees DavidMilstein Vol.29,2010 Vol.40,2012 MolecularOrganometallicMaterials OrganometallicsandRenewables forOptics VolumeEditors:MichaelA.R.Meier, VolumeEditors:H.LeBozec,V.Guerchais BertM.Weckhuysen,PieterC.A.Bruijnincx Vol.28,2010 Vol.39,2012 ConductingandMagneticOrganometallic TransitionMetalCatalyzedEnantioselective MolecularMaterials AllylicSubstitutioninOrganicSynthesis VolumeEditors:M.Fourmigue´,L.Ouahab VolumeEditor:UliKazmaier Vol.27,2009 Vol.38,2011 MetalCatalystsinOlefinPolymerization BifunctionalMolecularCatalysis VolumeEditor:Z.Guan VolumeEditors:T.Ikariya,M.Shibasaki Vol.26,2009 Vol.37,2011 Bio-inspiredCatalysts AsymmetricCatalysisfromaChinese VolumeEditor:T.R.Ward Perspective Vol.25,2009 VolumeEditor:ShengmingMa DirectedMetallation Vol.36,2011 VolumeEditor:N.Chatani Vol.24,2007 HigherOxidationStateOrganopalladium andPlatinumChemistry RegulatedSystemsforMultiphaseCatalysis VolumeEditor:A.J.Canty VolumeEditors:W.Leitner,M.Ho¨lscher Vol.35,2011 Vol.23,2008 IridiumCatalysis OrganometallicOxidationCatalysis VolumeEditor:P.G.Andersson VolumeEditors:F.Meyer,C.Limberg Vol.34,2011 Vol.22,2007 Inventing Reactions Volume Editor: Lukas J. Gooßen With Contributions by (cid:1) (cid:1) (cid:1) (cid:1) D.C. Behenna G.L. Beutner S.M. Bischof J.W. Bode B. Cardinal-David (cid:1) N. Chatani (cid:1) X. Cheng (cid:1) I. Cˇoric´ (cid:1) (cid:1) (cid:1) (cid:1) (cid:1) S.E. Denmark K. Fagnou K. Gooßen L.J. Gooßen (cid:1) (cid:1) (cid:1) B.G. Hashiguchi A.S.K. Hashmi T. Kawasaki M.M. Konnick (cid:1) B. List (cid:1) S. Mu¨ller (cid:1) R.A. Periana (cid:1) (cid:1) (cid:1) (cid:1) (cid:1) K.A. Scheidt K. Soai B.M. Stoltz D.R. Stuart (cid:1) (cid:1) (cid:1) M. Tobisu B.M. Trost S. Vellalath H. Yamamoto Editor LukasJ.Gooßen TUKaiserslautern FBChemie-OrganischeChemie Erwin-Schro¨dinger-Str.54 67663Kaiserslautern Germany ISSN1436-6002 ISSN1616-8534(electronic) ISBN978-3-642-34285-1 ISBN978-3-642-34286-8(eBook) DOI10.1007/978-3-642-34286-8 SpringerHeidelbergNewYorkDordrechtLondon LibraryofCongressControlNumber:2012950322 #Springer-VerlagBerlinHeidelberg2013 Thisworkissubjecttocopyright.AllrightsarereservedbythePublisher,whetherthewholeorpartof the material is concerned, specifically the rights of translation, reprinting, reuse of illustrations, recitation,broadcasting,reproductiononmicrofilmsorinanyotherphysicalway,andtransmissionor informationstorageandretrieval,electronicadaptation,computersoftware,orbysimilarordissimilar methodologynowknownorhereafterdeveloped.Exemptedfromthislegalreservationarebriefexcerpts inconnectionwithreviewsorscholarlyanalysisormaterialsuppliedspecificallyforthepurposeofbeing enteredandexecutedonacomputersystem,forexclusiveusebythepurchaserofthework.Duplication ofthispublicationorpartsthereofispermittedonlyundertheprovisionsoftheCopyrightLawofthe Publisher’s location, in its current version, and permission for use must always be obtained from Springer.PermissionsforusemaybeobtainedthroughRightsLinkattheCopyrightClearanceCenter. ViolationsareliabletoprosecutionundertherespectiveCopyrightLaw. Theuseofgeneraldescriptivenames,registerednames,trademarks,servicemarks,etc.inthispublication doesnotimply,evenintheabsenceofaspecificstatement,thatsuchnamesareexemptfromtherelevant protectivelawsandregulationsandthereforefreeforgeneraluse. Whiletheadviceandinformationinthisbookarebelievedtobetrueandaccurateatthedateofpublication, neithertheauthorsnortheeditorsnorthepublishercanacceptanylegalresponsibilityforanyerrorsor omissionsthatmaybemade.Thepublishermakesnowarranty,expressorimplied,withrespecttothe materialcontainedherein. Printedonacid-freepaper SpringerispartofSpringerScience+BusinessMedia(www.springer.com) Volume Editor LukasJ.Gooßen TUKaiserslautern FBChemie-OrganischeChemie Erwin-Schro¨dinger-Str.54 67663Kaiserslautern Germany [email protected] Editorial Board Prof.MatthiasBeller Prof.LouisS.Hegedus Leibniz-Institutfu¨rKatalysee.V. DepartmentofChemistry anderUniversita¨tRostock ColoradoStateUniversity Albert-Einstein-Str.29a FortCollins,Colorado80523-1872,USA 18059Rostock,Germany [email protected] [email protected] Prof.PeterHofmann Prof.JohnM.Brown Organisch-ChemischesInstitut ChemistryResearchLaboratory Universita¨tHeidelberg OxfordUniversity ImNeuenheimerFeld270 MansfieldRd., 69120Heidelberg,Germany OxfordOX13TA,UK [email protected] [email protected] Prof.TakaoIkariya Prof.PierreH.Dixneuf DepartmentofAppliedChemistry GraduateSchoolofScienceandEngineering CampusdeBeaulieu TokyoInstituteofTechnology Universite´deRennes1 2-12-1Ookayama,Meguro-ku, Av.duGlLeclerc Tokyo152-8552,Japan 35042RennesCedex,France [email protected] [email protected] Prof.LuisA.Oro Prof.AloisFu¨rstner InstitutoUniversitariodeCata´lisisHomoge´nea Max-Planck-Institutfu¨rKohlenforschung DepartmentofInorganicChemistry I.C.M.A.-FacultyofScience Kaiser-Wilhelm-Platz1 45470Mu¨lheimanderRuhr,Germany UniversityofZaragoza-CSIC Zaragoza-50009,Spain [email protected] [email protected] Prof.LukasJ.Gooßen Prof.Qi-LinZhou FBChemie-OrganischeChemie StateKeyLaboratoryofElemento-organic TUKaiserslautern Chemistry Erwin-Schro¨dinger-Str.Geb.54 NankaiUniversity 67663Kaiserslautern,German WeijinRd.94,Tianjin300071PRChina [email protected] [email protected] . Topics in Organometallic Chemistry Also Available Electronically Topics in Organometallic Chemistry is included in Springer’s eBook package ChemistryandMaterialsScience.Ifalibrarydoesnotoptforthewholepackagethe book series may be bought on a subscription basis. Also, all back volumes are availableelectronically. For all customers who have a standing order to the print version of Topics in Organometallic Chemistry, we offer free access to the electronic volumes of the SeriespublishedinthecurrentyearviaSpringerLink. Ifyoudonothaveaccess,youcanstillviewthetableofcontentsofeachvolume andtheabstractofeacharticlebygoingtotheSpringerLinkhomepage,clickingon “ChemistryandMaterialsScience,”underSubjectCollection,then“BookSeries,” underContentTypeandfinallybyselectingTopicsinOrganometallicChemistry. Youwillfindinformationaboutthe – EditorialBoard – AimsandScope – InstructionsforAuthors – SampleContribution at springer.com using the search function by typing in Topics in Organometallic Chemistry. ColorfiguresarepublishedinfullcolorintheelectronicversiononSpringerLink. Aims and Scope The series Topics in Organometallic Chemistry presents critical overviews of researchresultsinorganometallicchemistry.Asourunderstandingoforganometallic structures,propertiesandmechanismsgrows,newpathsareopenedforthedesign of organometallic compounds and reactions tailored to the needs of such diverse areas as organic synthesis, medical research, biology and materials science. Thus the scope of coverage includes a broad range of topics of pure and applied organometallic chemistry, where new breakthroughs are being made that are of significance to a larger scientific audience. The individual volumes of Topics in Organometallic Chemistry are thematic. Reviewarticlesaregenerallyinvitedbythevolumeeditors. In references Topics in Organometallic Chemistry is abbreviated Top Organomet Chem and iscited asajournal.From volume 29 onwards this series islistedwith ISI/WebofKnowledgeandincomingyearsitwillacquireanimpactfactor. vii . In memory of Professor Keith Fagnou, inventor of great chemical reactions .