Radicals in Synthesis III PDF
Preview Radicals in Synthesis III
320 Topics in Current Chemistry Editorial Board: K.N. Houk C.A. Hunter M.J. Krische J.-M. Lehn l l l S.V. Ley M. Olivucci J. Thiem M. Venturi P. Vogel l l l l C.-H. Wong H. Wong H. Yamamoto l l Topics in Current Chemistry Recently Published and Forthcoming Volumes RadicalsinSynthesisIII Bismuth-MediatedOrganicReactions VolumeEditors:MarkusR.Heinrich, VolumeEditor:ThierryOllevier AndreasGansa¨uer Vol.311,2012 Vol.320,2012 Peptide-BasedMaterials ChemistryofNanocontainers VolumeEditor:TimothyDeming VolumeEditors:MarkusAlbrecht, Vol.310,2012 F.EkkehardtHahn Vol.319,2012 AlkaloidSynthesis VolumeEditor:Hans-JoachimKno¨lker LiquidCrystals:MaterialsDesignand Vol.309,2012 Self-Assembly VolumeEditor:CarstenTschierske FluorousChemistry Vol.318,2012 VolumeEditor:Istva´nT.Horva´th Fragment-BasedDrugDiscoveryandX-Ray Vol.308,2012 Crystallography VolumeEditors:ThomasG.Davies, MultiscaleMolecularMethodsinApplied MarkoHyvo¨nen Chemistry Vol.317,2012 VolumeEditors:BarbaraKirchner, JadranVrabec NovelSamplingApproachesinHigher Vol.307,2012 DimensionalNMR VolumeEditors:MartinBilleter, SolidStateNMR VladislavOrekhov VolumeEditor:JerryC.C.Chan Vol.316,2012 Vol.306,2012 AdvancedX-RayCrystallography PrionProteins VolumeEditor:KariRissanen VolumeEditor:Jo¨rgTatzelt Vol.315,2012 Vol.305,2011 Pyrethroids:FromChrysanthemumtoModern Microfluidics:Technologiesand IndustrialInsecticide Applications VolumeEditors:NoritadaMatsuo,TatsuyaMori VolumeEditor:BingchengLin Vol.314,2012 Vol.304,2011 UnimolecularandSupramolecular Photocatalysis ElectronicsII VolumeEditor:CarloAlbertoBignozzi VolumeEditor:RobertM.Metzger Vol.303,2011 Vol.313,2012 ComputationalMechanismsofAuandPt UnimolecularandSupramolecular CatalyzedReactions ElectronicsI VolumeEditors:ElenaSoriano, VolumeEditor:RobertM.Metzger Jose´Marco-Contelles Vol.312,2012 Vol.302,2011 Radicals in Synthesis III Volume Editors: Markus R. Heinrich (cid:1) Andreas Gansa¨uer With Contributions by G.K. Friestad (cid:1) A. Gansa¨uer (cid:1) M.R. Heinrich (cid:1) I. Huth (cid:1) U. Jahn (cid:1) A.Kirste(cid:1)S.Mentizi(cid:1)J.E.Oltra(cid:1)M.Otte(cid:1)N.M.Padial(cid:1)G.Pratsch(cid:1) A. Rosales (cid:1) I. Sancho-Sanz (cid:1) L. Shi (cid:1) S.R. Waldvogel Editors Prof.Dr.MarkusR.Heinrich Prof.Dr.AndreasGansa¨uer PharmazeutischeChemie Kekule´Institutfu¨rOrganischeChemieund Departmentfu¨rChemieundPharmazieder BiochemiederUniversita¨tBonn Friedrich-Alexander-Universita¨t Bonn Erlangen-Nu¨rnberg Germany Erlangen Germany ISSN0340-1022 e-ISSN1436-5049 ISBN978-3-642-28122-8 e-ISBN978-3-642-28123-5 DOI10.1007/978-3-642-28123-5 SpringerHeidelbergDordrechtLondonNewYork LibraryofCongressControlNumber:2012932054 #Springer-VerlagBerlinHeidelberg2012 Thisworkissubjecttocopyright.Allrightsarereserved,whetherthewholeorpartofthematerialis concerned,specificallytherightsoftranslation,reprinting,reuseofillustrations,recitation,broadcasting, reproductiononmicrofilmorinanyotherway,andstorageindatabanks.Duplicationofthispublication orpartsthereofispermittedonlyundertheprovisionsoftheGermanCopyrightLawofSeptember9, 1965,initscurrentversion,andpermissionforusemustalwaysbeobtainedfromSpringer.Violations areliabletoprosecutionundertheGermanCopyrightLaw. 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Printedonacid-freepaper SpringerispartofSpringerScience+BusinessMedia(www.springer.com) Volume Editors Prof.Dr.MarkusR.Heinrich Prof.Dr.AndreasGansa¨uer PharmazeutischeChemie Kekule´ Institutfu¨rOrganischeChemieund Departmentfu¨rChemieundPharmazieder BiochemiederUniversita¨tBonn Friedrich-Alexander-Universita¨t Bonn Erlangen-Nu¨rnberg Germany Erlangen Germany Editorial Board Prof.Dr.KendallN.Houk Prof.Dr.StevenV.Ley UniversityofCalifornia UniversityChemicalLaboratory DepartmentofChemistryandBiochemistry LensfieldRoad 405HilgardAvenue CambridgeCB21EW LosAngeles,CA90024-1589,USA GreatBritain [email protected] [email protected] Prof.Dr.ChristopherA.Hunter Prof.Dr.MassimoOlivucci DepartmentofChemistry Universita`diSiena UniversityofSheffield DipartimentodiChimica SheffieldS37HF,UnitedKingdom ViaADeGasperi2 c.hunter@sheffield.ac.uk 53100Siena,Italy [email protected] Prof.MichaelJ.Krische Prof.Dr.JoachimThiem UniversityofTexasatAustin Institutfu¨rOrganischeChemie Chemistry&Biochemistry Department Universita¨tHamburg 1UniversityStationA5300 Martin-Luther-King-Platz6 AustinTX,78712-0165,USA 20146Hamburg,Germany [email protected] [email protected] Prof.Dr.Jean-MarieLehn Prof.Dr.MargheritaVenturi ISIS DipartimentodiChimica 8,alle´eGaspardMonge Universita`diBologna BP70028 viaSelmi2 67083StrasbourgCedex,France 40126Bologna,Italy [email protected] [email protected] vi EditorialBoard Prof.Dr.PierreVogel Prof.Dr.HenryWong LaboratoryofGlycochemistry TheChineseUniversityofHongKong andAsymmetricSynthesis UniversityScienceCentre EPFL–Ecolepolytechniquefe´derale DepartmentofChemistry deLausanne Shatin,NewTerritories EPFLSBISICLGSA [email protected] BCH5307(Bat.BCH) 1015Lausanne,Switzerland Prof.Dr.HisashiYamamoto pierre.vogel@epfl.ch ArthurHollyComptonDistinguished Prof.Dr.Chi-HueyWong Professor DepartmentofChemistry Professor of Chemistry, Scripps Research TheUniversityofChicago Institute 5735SouthEllisAvenue PresidentofAcademiaSinica Chicago,IL60637 AcademiaSinica 773-702-5059 128AcademiaRoad USA Section2,Nankang [email protected] Taipei115 Taiwan [email protected] Topics in Current Chemistry Also Available Electronically Topics in Current Chemistry is included in Springer’s eBook package Chemistry andMaterialsScience.Ifalibrarydoesnotoptforthewholepackagethebookseries may be bought on a subscription basis. Also, all back volumes are available electronically. Forallcustomerswithaprintstandingorderweofferfreeaccesstotheelectronic volumesoftheseriespublishedinthecurrentyear. Ifyoudonothaveaccess,youcanstillviewthetableofcontentsofeachvolume and the abstract of each article by going to the SpringerLink homepage, clicking on “Chemistry and Materials Science,” under Subject Collection, then “Book Series,”underContentTypeandfinallybyselectingTopicsinCurrentChemistry. Youwillfindinformationaboutthe –EditorialBoard –AimsandScope –InstructionsforAuthors –SampleContribution atspringer.comusingthesearchfunctionbytypinginTopicsinCurrentChemistry. ColorfiguresarepublishedinfullcolorintheelectronicversiononSpringerLink. Aims and Scope TheseriesTopics inCurrentChemistry presents criticalreviews ofthe present and futuretrendsinmodernchemicalresearch.Thescopeincludesallareasofchemical science,including theinterfaceswithrelated disciplines suchasbiology,medicine, andmaterialsscience. Theobjectiveofeachthematicvolumeistogivethenon-specialistreader,whether at the university or in industry, a comprehensive overview of an area where new insightsofinteresttoalargerscientificaudienceareemerging. vii viii TopicsinCurrentChemistryAlsoAvailableElectronically Thus each review within the volume critically surveys one aspect of that topic and places it within the context of the volume as a whole. The most significant developmentsofthelast5–10yearsarepresented,usingselectedexamplestoillus- trate the principles discussed. A description of the laboratory procedures involved is often useful to the reader. The coverage is not exhaustive in data, but rather conceptual, concentrating on the methodological thinking that will allow the non- specialistreadertounderstandtheinformationpresented. Discussionofpossiblefutureresearchdirectionsintheareaiswelcome. Reviewarticlesfortheindividualvolumesareinvitedbythevolumeeditors. InreferencesTopicsinCurrentChemistryisabbreviatedTop CurrChemandis citedasajournal. ImpactFactor2010:2.067;Section“Chemistry,Multidisciplinary”:Rank44of144 Preface Radical chemistry, as any sub-discipline of synthetic chemistry, has to meet ever morecomplexdemands,suchassustainabilityandselectivity,inordertobeapplied to the multifaceted challenges of today. In this volume of Topics in Current Chemistry,recentexcitingdevelopmentsthataddressthesehighlypertinentissues havebeensummarizedbyleadingscientistsofthefield. One of the economically and ecologically most attractive ways to generate radicalsiselectrochemistry.Newmaterials,suchastheBDDelectrodesdescribed here,willexpandtherelevanceofthisalreadyimportantarea.Arylationreactions are extremely important in synthesis in academic and industrial laboratories. The chemistryofarylradicalshighlightedheresummarizesmoderndevelopmentsthat are highly attractive for carrying out such transformations. The control of stereo- selectivity is of prime significance for any type of reactions. Radical addition to chiral hydrazones provides a convenient means for achieving this goal as also summarizedhere.Thereductiveterminationofradicals byhydrogenatomdonors hasalwaysbeenacriticalaspectofradicalchemistrywithrespecttoenvironmental issues and novel exciting developments addressing this key issue are discussed. Finally,theuseofradicalsaskeyintermediatesincatalysishasblossomedinrecent years.Thishighlyimportantfieldhasbeenreviewedcomprehensivelyforthefirst timeinthisissue.Specialemphasishasbeenlaidonallaspectsofselectivity. We hope that the exciting topics presented in this volume, ranging from the generationofradicalstoapplicationsincatalysis,willbeabletoconvincescientists atalllevelstoconsiderusingradicalmethodsintheirdailyworkandwillprovide furtherimpetusforthedevelopmentofnovelmethodsofradicalchemistry. ErlangenandBonn MarkusR.Heinrich December2011 AndreasGansa¨uer ix .
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