Bifunctional Molecular Catalysis PDF
Preview Bifunctional Molecular Catalysis
37 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 AsymmetricCatalysisfromaChinese Bio-inspiredCatalysts Perspective VolumeEditor:T.R.Ward VolumeEditor:ShengmingMa Vol.25,2009 Vol.36,2011 DirectedMetallation HigherOxidationStateOrganopalladium VolumeEditor:N.Chatani andPlatinumChemistry Vol.24,2007 VolumeEditor:A.J.Canty Vol.35,2011 RegulatedSystemsforMultiphaseCatalysis VolumeEditors:W.Leitner,M.Ho¨lscher IridiumCatalysis Vol.23,2008 VolumeEditor:P.G.Andersson Vol.34,2011 OrganometallicOxidationCatalysis IronCatalysis–Fundamentalsand VolumeEditors:F.Meyer,C.Limberg Applications Vol.22,2007 VolumeEditor:B.Plietker Vol.33,2011 N-HeterocyclicCarbenesinTransition MetalCatalysis MedicinalOrganometallicChemistry VolumeEditor:F.Glorius VolumeEditors:G.Jaouen,N.Metzler-Nolte Vol.21,2006 Vol.32,2010 C-XBondFormation DendrimerCatalysis VolumeEditor:A.Vigalok VolumeEditor:L.H.Gade Vol.31,2010 Vol.20,2006 TransitionMetalComplexesofNeutral MetalCatalyzedCascadeReactions h1-CarbonLigands VolumeEditor:T.J.J.Mu¨ller VolumeEditors:R.Chauvin,Y.Canac Vol.19,2006 Vol.30,2010 CatalyticCarbonylationReactions PhotophysicsofOrganometallics VolumeEditor:M.Beller VolumeEditor:A.J.Lees Vol.18,2006 Vol.29,2010 BioorganometallicChemistry MolecularOrganometallicMaterials VolumeEditor:G.Simonneaux forOptics Vol.17,2006 VolumeEditors:H.LeBozec,V.Guerchais Vol.28,2010 SurfaceandInterfacialOrganometallic ConductingandMagneticOrganometallic ChemistryandCatalysis MolecularMaterials VolumeEditors:C.Cope´ret,B.Chaudret VolumeEditors:M.Fourmigue´,L.Ouahab Vol.16,2005 Vol.27,2009 ChiralDiazaligandsforAsymmetric MetalCatalystsinOlefinPolymerization Synthesis VolumeEditor:Z.Guan VolumeEditors:M.Lemaire,P.Mangeney Vol.26,2009 Vol.15,2005 Bifunctional Molecular Catalysis (cid:1) Volume Editors: Takao Ikariya Masakatsu Shibasaki With Contributions by J.-E. Ba¨ckvall (cid:1) C.P. Casey (cid:1) C. Gunanathan (cid:1) T. Ikariya (cid:1) (cid:1) (cid:1) (cid:1) (cid:1) (cid:1) J.-i. Ito K. Kamata M. Kanai N. Kumagai P. Li (cid:1) (cid:1) (cid:1) (cid:1) S. Matsunaga D. Milstein N. Mizuno H. Nishiyama (cid:1) (cid:1) (cid:1) M. Shibasaki M.C. Warner K. Yamaguchi H. Yamamoto Editors Prof.Dr.TakaoIkariya Prof.Dr.MasakatsuShibasaki DepartmentofAppliedChemistry InstituteofMicrobialChemistry GraduateSchoolofScience 3-14-23Kamiosaki andEngineering Shinagawa-ku TokyoInstituteofTechnology Tokyo141-0021 2-12-1Ookayama,Meguro-ku Japan Tokyo152-8552 [email protected] Japan [email protected] ISBN978-3-642-20730-3 e-ISBN978-3-642-20731-0 DOI10.1007/978-3-642-20731-0 SpringerHeidelbergDordrechtLondonNewYork LibraryofCongressControlNumber:2011929692 #Springer-VerlagBerlinHeidelberg2011 Thisworkissubjecttocopyright.Allrightsarereserved,whetherthewholeorpartofthematerialis concerned,specificallytherightsoftranslation,reprinting,reuseofillustrations,recitation,broadcasting, reproductiononmicrofilmorinanyotherway,andstorageindatabanks.Duplicationofthispublication orpartsthereofispermittedonlyundertheprovisionsoftheGermanCopyrightLawofSeptember9, 1965,initscurrentversion,andpermissionforusemustalwaysbeobtainedfromSpringer.Violations areliabletoprosecutionundertheGermanCopyrightLaw. Theuseofgeneraldescriptivenames,registerednames,trademarks,etc.inthispublicationdoesnot imply, even in the absence of a specific statement, that such names are exempt from the relevant protectivelawsandregulationsandthereforefreeforgeneraluse. Coverdesign:eStudioCalamar,Spain Printedonacid-freepaper SpringerispartofSpringerScience+BusinessMedia(www.springer.com) Volume Editors Prof.Dr.TakaoIkariya Prof.Dr.MasakatsuShibasaki DepartmentofAppliedChemistry InstituteofMicrobialChemistry GraduateSchoolofScience 3-14-23Kamiosaki andEngineering Shinagawa-ku TokyoInstituteofTechnology Tokyo141-0021 2-12-1Ookayama,Meguro-ku Japan Tokyo152-8552 [email protected] Japan [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 Catalysts are crucial, not only for the production of many thousands of materials andproducts,includingfuelsrequiredbymodernsociety,butalsoforthereduction ofwaterandairpollution,aswellastominimizethewasteofnaturalresourcesand energy.Recentadvancesingreenandsustainablescienceandtechnologydemand more powerful and sophisticated catalysts, which have a tunable function. Much efforts have been paid to the development of well-defined bifunctional molecular catalystsbasedonthecombinationofLewisacidandbasicsitesworkinginconcert to attain highly efficient molecular transformation for organic synthesis. Bifunc- tional catalysts contain two or more sites for the activation of electrophiles and nucleophiles,andconsequentlythesecatalystscanefficientlypromoteawiderange of molecular transformation by effective accumulation and cooperative activation of reacting substrates on the neighboring active centers in the same molecules. Carefulandprecisetuningofthestructuresofthemolecularcatalysts,aswellasthe spatial organization of the functionality, is required to achieve the best catalysis performance. Metal–ligand cooperating bifunctional molecular catalysts are also recognized as an alternative and indispensable strategy to realize highly effective molecular transformation.Thenon-innocentligandthereindirectlyparticipatesinthesubstrate activationandsubsequentreactionsthroughvarioussecondaryinteractionsinclud- ing hydrogen bonding. Therefore, the catalyst deactivation due to the acid–base neutralization or destructive aggregation can be minimized. Indeed, a number of biological catalyses in nature have been performed in a sophisticated manner on such bifunctional and even multifunctional systems with ligated peptide residues andprostheticgroups. Thisuniqueconceptoftherecentlydevelopedbifunctionalmetal-basedmolec- ular catalysts leads to high reaction rates and excellent stereochemical outcome becausethereactionsproceedthroughaclosedassemblyofreactantsandcatalysts, providing awide substrate scope andapplicabilityin organic synthetic chemistry. This volume is intended to highlight the recent exciting advances in bifunctional catalysis with well-designed multimetallic systems, dinuclear, mononuclear ix x Preface transition metal-based molecular catalysts, and Lewis acid catalysts. All chapters have been written with a brief introduction on the definition and concept of bifunctionality by leading chemists in the corresponding research area. We wish to express our sincere thanks to them for their contributions and fruitful and exciting collaboration in publishing a book dealing with the most recent achieve- mentinthisfield:MotomuKanai,ShigekiMatsunaga,NaoyaKumagai,Madeleine C. Warner, Charles P. Casey, Jan-E. Ba¨ckvall, Chidambaram Gunanathan, David Milstein, Noritaka Mizuno, Keigo Kamata, Kazuya Yamaguchi, Pingfan Li, Hisashi Yamamoto, Jun-ichi Ito, Hisao Nishiyama. We are also grateful for all help and supports from Springer, in particular, from Drs. Elizabeth Hawkins and JuttaLindenborn. We hope not only that this book will be useful to researchers and students already involved in organic synthesisand molecular catalysis,but also thatit will attractscientistsworkinginvariousfieldofchemistry. Tokyo,Japan TakaoIkariya MasakatsuShibasaki
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