Synthesis and Application of Organoboron Compounds PDF
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Topics in Organometallic Chemistry 49 Elena Fernández Andrew Whiting Editors Synthesis and Application of Organoboron Compounds 49 Topics in Organometallic Chemistry Editorial Board M. Beller, Rostock, Germany J.M. Brown, Oxford, United Kingdom P.H. Dixneuf, Rennes, France J. Dupont, Porto Alegre, Brazil A. Fu¨rstner, Mu¨lheim, Germany Frank Glorius, Mu¨nster, Germany L.J. Gooßen, Kaiserslautern, Germany T. Ikariya, Tokyo, Japan S. Nolan, St Andrews, United Kingdom Jun Okuda, Aachen, Germany L.A. Oro, Zaragoza, Spain Q.-L. Zhou, Tianjin, China Aims and Scope TheseriesTopicsinOrganometallicChemistrypresentscriticaloverviewsofresearch resultsinorganometallicchemistry.Asourunderstandingoforganometallicstructure, properties and mechanisms increases, new ways are opened for the design of organometalliccompoundsandreactionstailoredtotheneedsofsuchdiverseareasas organicsynthesis,medicalresearch,biologyandmaterialsscience.Thusthescopeof coverage includes a broad range of topics of pure and applied organometallic chemistry,wherenewbreakthroughsarebeingachievedthatareofsignificancetoa largerscientificaudience. TheindividualvolumesofTopicsinOrganometallicChemistryarethematic.Review articles are generally invited by the volume editors. All chapters from Topics in Organometallic Chemistry are published OnlineFirst with an individual DOI. Inreferences,TopicsinOrganometallicChemistryisabbreviatedasTopOrganomet Chemandcitedasajournal. Moreinformationaboutthisseriesat http://www.springer.com/series/3418 (cid:129) Elena Fernández Andrew Whiting Editors Synthesis and Application of Organoboron Compounds With contributions by (cid:1) (cid:1) (cid:1) (cid:1) V.K. Aggarwal D.G. Hall T.N. Hooper M.J. Ingleson N. Ishid (cid:1) K. Ishihara (cid:1) F. Ja¨kle (cid:1) H.C. Johnson (cid:1) S. Lee (cid:1) (cid:1) (cid:1) (cid:1) (cid:1) D. Leonori G.A. Molander M. Murakami K. Nozaki (cid:1) (cid:1) (cid:1) (cid:1) H-Y. Sun K.M. Traister A.S. Weller M. Yamashita J. Yun Editors ElenaFerna´ndez AndrewWhiting UniversitatRoviraiVirgiliDirectora DepartmentofChemistry TECAT CentreforSustainableChemicalProcesses Tarragona Durham Spain UnitedKingdom ISSN1436-6002 ISSN1616-8534(electronic) ISBN978-3-319-13053-8 ISBN978-3-319-13054-5(eBook) DOI10.1007/978-3-319-13054-5 SpringerChamHeidelbergNewYorkDordrechtLondon LibraryofCongressControlNumber:2015933846 ©SpringerInternationalPublishingSwitzerland2015 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. The use of general descriptive names, registered names, trademarks, service marks, etc. in this publicationdoesnotimply,evenintheabsenceofaspecificstatement,thatsuchnamesareexempt fromtherelevantprotectivelawsandregulationsandthereforefreeforgeneraluse. While the advice and information in this book are believed to be true and accurate at the date of publication,neithertheauthorsnortheeditorsnorthepublishercanacceptanylegalresponsibilityfor anyerrorsoromissionsthatmaybemade.Thepublishermakesnowarranty,expressorimplied,with respecttothematerialcontainedherein. Printedonacid-freepaper SpringerispartofSpringerScience+BusinessMedia(www.springer.com) Preface Fromtheearlyexplorativedaysoforganoboronchemistrytothepresentday,this area has never ceased to be a vital and exciting area of chemical research. Major themes have emerged, one after another, keeping organoboron chemistry at the forefrontofourscience,perhapsstartingwithmajorandlong-termcontributionsof H. C. Brown. His work gave us the possibility to hydroborate and off-the-shelf hydride reducing agents thatwenowtakeforgranted, andofcourse, thiscontrib- utedtohisNobelPrizein1979.Organoboronchemistrymovedfromstoichiometric to a catalytic manifold, and this fact opened up unexpected applications and unlimited possibilities. In addition to these fundamental studies elucidating the basicsoforganoboronchemistry,thereweremajorstridesintoasymmetricsynthe- sisandthiscontributedtoourscienceininnumerousways,allowingustoroutinely achieve non-chiral pool synthesis of chiral molecules. Further remarkable contri- butions carried out by D. S. Matteson have laid the foundations for considerable amounts of the research reported in this book. Along the way, A. Suzuki and N. Miyaura found new uses for organoboron compounds in cross-coupling reac- tions, creating major impacts upon the way in which we assemble molecules, especiallyusingautomatedsystemsforbiologicalevaluation.Inturn,andfollowing fundamentalstudiesbyE.Vedejs,newtypesoforganoboroncompoundswerespun outwhichpushedforwardtheboundariesofstabilityandcreatedanever-widening range of applications for further synthetic transformations. Interestingly, we still neednewways,notonlytomakeorganoboroncompounds,buttoexploitthehuge and untapped potential for these compounds. In this book, we can see how new methods for the introduction of boron into carbon frameworks are creating their own revolutions of what is possible to make, and this science is moving on from simple boron-based Lewis acid catalysis to new types of activation pathways and whoknowsexactlywherethiswillleadus.Onethingiscertainofcourse,forthose ofuswhoareaddictedtoorganoboronchemistry,itwillcontinuetostimulateand evenbetter,surprise.Wehopethissnapshotofwhereorganoboronistodaywillnot onlybeavitalreferencebookbutwehopeitwillprovideyouwithaninsightinto wherethingsmightgointhefuture,andmaybeitwillsparkthatideathatopensthe wayforyetanothermajoradvanceinourscience. v vi Preface Finally, as editors, we would like to thank all the contributors for their partic- ipation in this project, both authors of chapters and reviewers (Holger Braun- schweig, Warren E. Piers, Webster Santos, Kalman J. Szabo´, Bertrand Carboni, R. Tom Baker, Jo¨rg Pietruszka, Tom Sheppard, and Emmanuel Lacoˆte). We appreciate their efforts to complete the chapters and revisions on time and for all the constructive and positive comments we have received from them along this periodofgestationoftheentirebook. Tarragona,Spain ElenaFerna´ndez Durham,UK AndrewWhiting Contents BorylAnions. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1 MakotoYamashitaandKyokoNozaki FundamentalandAppliedPropertiesofBorocations. . . . . . . . . . . . . 39 MichaelJ.Ingleson AsymmetricCatalyticBorylationofα,β-UnsaturatedAcceptors. . . . . 73 SuminLeeandJaesookYun ReactionsofAlkynylboronCompounds. . . . . . . . . . . . . . . . . . . . . . . . 93 NaokiIshidaandMasahiroMurakami ImprovingTransformationsThroughOrganotrifluoroborates. . . . . . 117 KaitlinM.TraisterandGaryA.Molander TheCatalyticDehydrocouplingofAmine–Boranesand Phosphine–Boranes. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 153 HeatherC.Johnson,ThomasN.Hooper,andAndrewS.Weller AttheForefrontoftheSuzuki–MiyauraReaction:Advancesin StereoselectiveCross-Couplings. . . .. . . . . . . .. . . . . . . .. . . . . . . .. . 221 Ho-YanSunandDennisG.Hall BoronicAcid-CatalyzedReactionsofCarboxylicAcids. . . . . . . . . . . . 243 KazuakiIshihara Reagent-ControlledLithiation–Borylation. . . . . .. . . . . . . . . . . . . .. . 271 DanieleLeonoriandVarinderK.Aggarwal RecentAdvancesintheSynthesisandApplicationsofOrganoborane Polymers. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 297 FriederJa¨kle Index. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 327 vii Boryl Anions MakotoYamashitaandKyokoNozaki Contents 1 Introduction:HistoryofBorylAnionsBefore2006........................................ 2 2 ChemistryofBorylAnions.................................................................. 3 2.1 Base-StabilizedBorylAnions.......................................................... 4 2.2 N-HeterocyclicBorylAnions.......................................................... 7 2.3 BorylAnionDerivativesasaCounterpartofCarboanions........................... 12 2.4 Base-CoordinatedDiborane(4)asBorylAnionEquivalents......................... 18 3 ChemistryofBoryl–TransitionMetalComplexesDerivedfromBorylAnion............ 22 3.1 BorylComplexesofLateTransitionMetals(Groups11–12)........................ 23 3.2 BorylComplexesofEarlyTransitionMetals(Groups3–5).......................... 25 4 ChemistryofBoryl-SubstitutedMainGroupElementCompoundsDerivedfromBoryl Anions......................................................................................... 27 4.1 Boryl-SubstitutedGroup13ElementCompounds.................................... 28 4.2 Boryl-SubstitutedGroup14ElementCompounds.................................... 31 4.3 Boryl-SubstitutedGroup15ElementCompounds.................................... 33 5 SummaryandOutlook....................................................................... 33 References........................................................................................ 34 M.Yamashita(*) DepartmentofAppliedChemistry,ChuoUniversity,1-13-27Kasuga,Bunkyo-ku,Tokyo112- 8551,Japan e-mail:[email protected] K.Nozaki(*) DepartmentofChemistryandBiotechnology,TheUniversityofTokyo,7-3-1Hongo, Bunkyo-ku,Tokyo113-8656,Japan e-mail:[email protected] ©SpringerInternationalPublishingSwitzerland2015 1 E.Ferna´ndez,A.Whiting(eds.),SynthesisandApplicationofOrganoboron Compounds,TopicsinOrganometallicChemistry49, DOI10.1007/978-3-319-13054-5_1 2 M.YamashitaandK.Nozaki Abstract Thischapterfocusesonthechemistryofborylanions.Thefirstsection givesabriefhistoryofborylanionbeforethefirstisolatedborylanionequivalent, boryllithium, emerged. Synthesis and properties of all existing boryl anions are summarizedinthesecondsection.Inthethirdsection,examplesofboryl–transition metalcomplexessynthesizedfromborylanionreagentsarepresented.Thefollow- ing fourth section describes chemistry of boryl-substituted main group element compoundsmadefromborylanions.Attheendofthischapter,theauthorsprovide asummaryandtheirperspectiveforrelatedfields. Keywords Boryl anions (cid:129) Boryl–transition metal complexes (cid:129) Boryllithium (cid:129) Boryl-substitutedmaingroupelements 1 Introduction: History of Boryl Anions Before 2006 Boronisagroup13elementinthesecondperiod,locatedontheleft-handsideof carbonintheperiodictable.Sinceatomicboronhasthreevalenceelectrons,neutral boronmoleculesgenerallyhavesixvalenceelectronsandavacantp-orbitalonthe boron center. This nature characterizes the chemistry of boron compounds as electron-deficient species in organic and inorganic chemistry fields. For example, the Lewis acidity of boron-containing compounds has been widely utilized for organic chemistry, such as hydroboration chemistry [1–3], Lewis-acidic boron- mediated chemistry [4], boron-enolate chemistry [5], and Suzuki–Miyaura cross- coupling chemistry [6–8]. To synthesize these types of boron-containing com- pounds, a boron-containing chemical bond should be constructed. In general, the existence of a vacant p-orbital of the boron atom in boron-containing reagents allowsustoaddnucleophilestothemtoformaboron–nucleophilebond.However, therehavebeenlimitedexamplesof“borylanions,”whichhaveaformallonepair and nucleophilicity on the boron atom. In this chapter, the authors summarize the chemistryofborylanions. (cid:1) Aparentborylanion,:BH ,wascalculatedtohaveasingletgroundstate[9],in 2 contrast to the case of the isoelectronic parent carbene, :CH , which has a triplet 2 groundstate[10].Theparentborylanioncouldbethermodynamicallystabilizedby complexation with a lithium cation and by substitution of hydrogen atoms with electronegative nitrogen and oxygen atoms [9]. The latter stabilization could be explained bytwo factors:(1)σ-acceptingcharacter ofelectronegative nitrogenand oxygenatomsand(2)π-donationfromthelonepairsoftheseheteroatoms.Further stabilization could be expected by the introduction of a boron-containing five- memberedringsystem[11,12],ashasbeencommontosynthesizetheisoelectronic N-heterocycliccarbenes(NHCs)[13].Beforethefirstachievementoftheisolationof aborylanion,asdescribedinSect.2,thehistoryofborylanionsshouldbenotedhere.
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