Organometallics as Catalysts in the Fine Chemical Industry PDF
Preview Organometallics as Catalysts in the Fine Chemical Industry
42 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 ModernOrganoaluminumReagents: C-XBondFormation Preparation,Structure,ReactivityandUse VolumeEditor:A.Vigalok VolumeEditors:SimonWoodward, Vol.31,2010 SamuelDagorne TransitionMetalComplexesofNeutral Vol.41,2012 h1-CarbonLigands OrganometallicPincerChemistry VolumeEditors:R.Chauvin,Y.Canac VolumeEditors:GerardvanKoten, Vol.30,2010 DavidMilstein PhotophysicsofOrganometallics Vol.40,2012 VolumeEditor:A.J.Lees Vol.29,2010 OrganometallicsandRenewables VolumeEditors:MichaelA.R.Meier, MolecularOrganometallicMaterials BertM.Weckhuysen,PieterC.A.Bruijnincx forOptics Vol.39,2012 VolumeEditors:H.LeBozec,V.Guerchais Vol.28,2010 TransitionMetalCatalyzedEnantioselective ConductingandMagneticOrganometallic AllylicSubstitutioninOrganicSynthesis MolecularMaterials VolumeEditor:UliKazmaier VolumeEditors:M.Fourmigue´,L.Ouahab Vol.38,2011 Vol.27,2009 BifunctionalMolecularCatalysis MetalCatalystsinOlefinPolymerization VolumeEditors:T.Ikariya,M.Shibasaki VolumeEditor:Z.Guan Vol.37,2011 Vol.26,2009 AsymmetricCatalysisfromaChinese Bio-inspiredCatalysts Perspective VolumeEditor:T.R.Ward VolumeEditor:ShengmingMa Vol.25,2009 Vol.36,2011 DirectedMetallation VolumeEditor:N.Chatani HigherOxidationStateOrganopalladium Vol.24,2007 andPlatinumChemistry VolumeEditor:A.J.Canty RegulatedSystemsforMultiphaseCatalysis Vol.35,2011 VolumeEditors:W.Leitner,M.Ho¨lscher Vol.23,2008 IridiumCatalysis VolumeEditor:P.G.Andersson OrganometallicOxidationCatalysis Vol.34,2011 VolumeEditors:F.Meyer,C.Limberg Vol.22,2007 IronCatalysis–Fundamentalsand N-HeterocyclicCarbenesinTransition Applications MetalCatalysis VolumeEditor:B.Plietker VolumeEditor:F.Glorius Vol.33,2011 Vol.21,2006 MedicinalOrganometallicChemistry DendrimerCatalysis VolumeEditors:G.Jaouen,N.Metzler-Nolte VolumeEditor:L.H.Gade Vol.32,2010 Vol.20,2006 Organometallics as Catalysts in the Fine Chemical Industry (cid:1) Volume Editors: Matthias Beller Hans-Ulrich Blaser With Contributions by (cid:1) (cid:1) (cid:1) (cid:1) H.-U. Blaser C.-y. Chen C.J. Cobley J.G. de Vries (cid:1) (cid:1) (cid:1) (cid:1) P. Dupau I.N. Houpis A.F. Indolese B. Pugin (cid:1) (cid:1) P. Ryberg F. Spindler G.T. Whiteker Editors MatthiasBeller Hans-UlrichBlaser Universita¨tRostock ScientificAdvisor Leibniz-Institutfu¨rOrganischeKatalyse SolviasAG Rostock Basel Germany Switzerland ISBN978-3-642-32832-9 ISBN978-3-642-32833-6(eBook) DOI10.1007/978-3-642-32833-6 SpringerHeidelbergNewYorkDordrechtLondon LibraryofCongressControlNumber:2012945424 #Springer-VerlagBerlinHeidelberg2012 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 Editors Prof.Dr.MatthiasBeller Dr.Hans-UlrichBlaser Universita¨tRostock ScientificAdvisor Leibniz-Institutfu¨rOrganischeKatalyse SolviasAG Rostock Basel Germany Switzerland [email protected] [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 is listedwith ISI/WebofKnowledgeandincomingyearsitwillacquireanimpactfactor. vii . Preface Although organometallic catalysts have been used on a large scale for the manu- facture of bulk chemicals for many years, their application in the fine chemicals industry is more recent. Despite the high impact of homogeneous catalysts on organic chemistry, highlighted by three Nobel Prizes in the last decade, their application for the industrial synthesis of more complex molecules is growing rather slowly. The main purpose of this volume is to illustrate the potential of organometalliccatalysisforthemanufactureofintermediatesandproductsasthey areencounteredinthefinechemicals,agrochemicals,orpharmaceuticalsindustry. The focus is on realized industrial applications described exclusively by authors experienced with concrete, “real-world” synthetic challenges. Discussed are pro- blems thatcan arisewhenmorecomplex,multifunctionalsubstratesare involved, aswellassuccessfulapproachestotackletheseproblems. Thevariouschaptersdemonstratetoorganicchemistsworkinginprocessdesign and development that organometallic catalysis is not just an academic toy, but is really a suitable tool for the large-scale production of complex intermediates. Thebookwillhopefullyalsoserveasasourceofinformationandprovideinspira- tionforacademicresearchers. Thebookconsistsoftwotypesofcontributions,overviewchaptersonselected technologiesandcasestudies.Consideringthatpublishingisnotatoppriorityfor industrialscientists,weareveryhappythatwecouldfindcompetentauthorsinboth categories. The technology chapters cover the most important reaction types used in the industry:JohannesG.deVries(DSM)givesanoverviewon“Palladium-Catalysed Coupling Reactions”; Gregory T. Whiteker (Dow AgroSciences) and Christopher J. Cobley (Chirotech Technology) review “Applications of Rhodium-Catalyzed HydroformylationinthePharmaceutical,AgrochemicalandFragranceIndustries”; PhilippeDupau(Firmenich)describesthe“Ruthenium-CatalyzedSelectiveHydro- genation for Flavor and Fragrance Applications”; and Hans-Ulrich Blaser, Benoˆıt Pugin, and Felix Spindler (Solvias) have authored the chapter on “Asymmetric Hydrogenation.” ix x Preface Case studies have been written by Ioannis Houpis (Janssen Pharmaceutica) on “Sequential Pd-catalyzed Cross Coupling Reactions; Challenges on Scale-up,” byAdrianoF.Indolese(RohnerChem)on“PilotPlantScaleSynthesisofanAryl- indole – Scale up of a Suzuki Coupling,” by Per Ryberg (AstraZeneca) on the “Development of a Mild and Robust Method for Palladium Catalysed Cyanation on Large Scale,” and by Cheng-yi Chen (Merck Research Laboratories) on the “Application of Ring Closing Metathesis Strategy to the Synthesis of Vaniprevir (MK-7009),a20-MemberedMacrocyclicHCVProteaseInhibitor.” Wethankalltheauthorsfortheireffortsandwehopethatourreadersfindtheir contributionsenlightening. Rostock,Germany MatthiasBeller Basel,Switzerland Hans-UlrichBlaser
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