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Advances in Organometallic Chemistry, Vol. 48 PDF

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Advances in ORGANOMETALLIC CHEMISTRY VOLUME 48 This Page Intentionally Left Blank Advances in Organometallic Chemistry EDITEDBY ROBERT WEST ANTHONY F. HILL DEPARTMENTOFCHEMISTRY DEPARTMENTOFCHEMISTRY UNIVERSITYOFWISCONSIN IMPERIALCOLLEGEOFSCIENCE MADISON,WISCONSIN TECHNOLOGY,ANDMEDICINE LONDON,ENGLAND FOUNDINGEDITOR F.GORDONA.STONE VOLUME 48 SanDiego SanFrancisco NewYork Boston London Sydney Tokyo Thisbookisprintedonacid-freepaper. (cid:3)∞ Copyright(cid:3)C 2001byACADEMICPRESS AllRightsReserved. Nopartofthispublicationmaybereproducedortransmittedinanyformorbyany means,electronicormechanical,includingphotocopy,recording,oranyinformation storageandretrievalsystem,withoutpermissioninwritingfromthePublisher. Theappearanceofthecodeatthebottomofthefirstpageofachapterinthisbook indicatesthePublisher’sconsentthatcopiesofthechaptermaybemadefor personalorinternaluseofspecificclients.Thisconsentisgivenonthecondition, however,thatthecopierpaythestatedpercopyfeethroughtheCopyrightClearance Center,Inc.(222RosewoodDrive,Danvers,Massachusetts01923),forcopying beyondthatpermittedbySections107or108oftheU.S.CopyrightLaw.Thisconsent doesnotextendtootherkindsofcopying,suchascopyingforgeneraldistribution,for advertisingorpromotionalpurposes,forcreatingnewcollectiveworks,orforresale. Copyfeesforpre-2001chaptersareasshownonthetitlepages.Ifnofeecode appearsonthetitlepage,thecopyfeeisthesameasforcurrentchapters. 0065-3055/2001$35.00 ExplicitpermissionfromAcademicPressisnotrequiredtoreproduceamaximumof twofiguresortablesfromanAcademicPresschapterinanotherscientificorresearch publicationprovidedthatthematerialhasnotbeencreditedtoanothersourceandthat fullcredittotheAcademicPresschapterisgiven. AcademicPress AdivisionofHarcourt,Inc. 525BStreet,Suite1900,SanDiego,California92101-4495,USA http://www.academicpress.com AcademicPress HarcourtPlace,32JamestownRoad,LondonNW17BY,UK http://www.academicpress.com InternationalStandardBookNumber:0-12-031148-8 PRINTEDINTHEUNITEDSTATESOFAMERICA 01 02 03 04 05 06 EB 9 8 7 6 5 4 3 2 1 Contents CONTRIBUTORS . . . . . . . . . . . . . . . . . . . . . . . . . . . vii MetalComplexesofStableCarbenes WOLFGANGHERMANN,THOMASWESKAMP, andVOLKERP.W.BO¨HM I. Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . 1 II. MetalComplexes . . . . . . . . . . . . . . . . . . . . . . . . 8 III. ApplicationsinHomogeneousCatalysis . . . . . . . . . . . . . . . 35 IV. OtherApplications . . . . . . . . . . . . . . . . . . . . . . . . 55 V. Summary. . . . . . . . . . . . . . . . . . . . . . . . . . . . 58 References . . . . . . . . . . . . . . . . . . . . . . . . . . . 59 TransitionMetalChemistryof1,3-Diynes,Poly-ynes, andRelatedCompounds PAULJ.LOWandMICHAELI.BRUCE I. Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . 72 II. DiynylComplexes,M{(C C) R} (n=1,2) . . . . . . . . . . . . . 74 2 n III. Di-andPoly-yneπComplexeswithOneorTwoMetalCenters . . . . . . 102 IV. MetalClusterComplexesDerivedfrom1,3-DiynesorPoly-ynes . . . . . . 130 V. σ,π-DiynylComplexes . . . . . . . . . . . . . . . . . . . . . . 164 VI. σ,π-DiyneComplexesofGroups3,4,and5 . . . . . . . . . . . . . . 177 VII. OtherReactionsofDiyneswithMetalComplexes. . . . . . . . . . . . 199 VIII. FormationofFreeDi-andPoly-ynesbyReactionsatMetalCenters. . . . . 224 IX. LigandsContainingDiyneGroups. . . . . . . . . . . . . . . . . . 226 X. SpectroscopicProperties,ElectronicStructure,andRedoxBehavior. . . . . 241 XI. MetalladiynesandRelatedComplexes . . . . . . . . . . . . . . . . 254 XII. PolymerandMaterialsChemistry . . . . . . . . . . . . . . . . . . 262 XIII. Prognosis . . . . . . . . . . . . . . . . . . . . . . . . . . . 263 XIV. Appendix:Abbreviations . . . . . . . . . . . . . . . . . . . . . 265 XV. Addendum . . . . . . . . . . . . . . . . . . . . . . . . . . . 266 References . . . . . . . . . . . . . . . . . . . . . . . . . . . 270 v vi Contents OrganoelementChemistryofMainGroup PorphyrinComplexes PENELOPEJ.BROTHERS I. Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . 289 II. Boron . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 294 III. Aluminum . . . . . . . . . . . . . . . . . . . . . . . . . . . 295 IV. Gallium,Indium,andThallium . . . . . . . . . . . . . . . . . . . 303 V. Silicon,Germanium,andTin . . . . . . . . . . . . . . . . . . . . 311 VI. Phosphorus,Arsenic,andAntimony . . . . . . . . . . . . . . . . . 321 VII. MainGroupPorphyrinComplexesContainingMetal MetalBonds. . . . . 331 References . . . . . . . . . . . . . . . . . . . . . . . . . . . 337 INDEX . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 343 CUMULATIVELISTOFCONTRIBUTORSFORVOLUMES1–36 . . . . . . . . . . 349 CUMULATIVEINDEXFORVOLUMES37–48 . . . . . . . . . . . . . . . . . 353 Contributors Numbersinparenthesesindicatethepagesonwhichtheauthors’contributionsbegin. VOLKER P. W. BO¨HM (1), Department of Chemistry, University of North Carolina at ChapelHill,ChapelHill,NorthCarolina27599 PENELOPEJ.BROTHERS(289),DepartmentofChemistry,TheUniversityofAuckland, Auckland,NewZealand MICHAELI.BRUCE(71),DepartmentofChemistry,UniversityofAdelaide,Adelaide, SouthAustralia5005,Australia WOLFGANG A. HERRMANN (1), Anorganisch-chemisches Institut der Technischen Universita¨tMu¨nchen,D-85747GarchingbeiMu¨nchen,Germany PAULJ.LOW(71),DepartmentofChemistry,UniversityofDurham,DurhamDH13LE, England THOMASWESKAMP(1),SymyxTechnologies,SantaClara,California95051 vii This Page Intentionally Left Blank ADVANCESINORGANOMETALLICCHEMISTRY,VOL.48 Metal Complexes of Stable Carbenes* WOLFGANG A. HERRMANN Anorganisch-chemischesInstitutderTechnischenUniversita¨tMu¨nchen D-85747GarchingbeiMu¨nchen,Germany THOMAS WESKAMP SymyxTechnologies SantaClara,California95051 ¨ VOLKER P. W. BOHM DepartmentofChemistry UniversityofNorthCarolinaatChapelHill ChapelHill,NorthCarolina27599-3290 I. Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1 A. HistoricBackground . . . . . . . . . . . . . . . . . . . . . . . 1 B. StableCarbenes . . . . . . . . . . . . . . . . . . . . . . . . . 3 C. PrecursorsforStableCarbenes . . . . . . . . . . . . . . . . . . . 5 II. MetalComplexes . . . . . . . . . . . . . . . . . . . . . . . . . . 8 A. Main-GroupMetalComplexes . . . . . . . . . . . . . . . . . . . 8 B. TransitionMetalComplexes . . . . . . . . . . . . . . . . . . . . 11 C. PropertiesofNHCLigands . . . . . . . . . . . . . . . . . . . . . 31 III. ApplicationsinHomogeneousCatalysis . . . . . . . . . . . . . . . . . 35 A. OlefinMetathesis . . . . . . . . . . . . . . . . . . . . . . . . 36 B. Heck-TypeReactions . . . . . . . . . . . . . . . . . . . . . . . 42 C. OtherReactions . . . . . . . . . . . . . . . . . . . . . . . . . 47 D. Heterogenization . . . . . . . . . . . . . . . . . . . . . . . . . 51 E. AsymmetricCatalysis . . . . . . . . . . . . . . . . . . . . . . . 53 F. High-ThroughputScreening . . . . . . . . . . . . . . . . . . . . 54 IV. OtherApplications . . . . . . . . . . . . . . . . . . . . . . . . . . 55 A. MaterialsScience . . . . . . . . . . . . . . . . . . . . . . . . 55 B. BioinorganicChemistry . . . . . . . . . . . . . . . . . . . . . . 56 C. MedicinalChemistry . . . . . . . . . . . . . . . . . . . . . . . 57 V. Summary . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 58 References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 59 I INTRODUCTION A. HistoricBackground Carbenes—moleculeswithaneutraldicoordinatecarbonatom—haveplayedan importantroleinorganicchemistryeversincetheirfirstfirmevidenceofexistence. ∗DedicatedtoProfessorHenriBrunnerontheoccasionofhis65thbirthday. 1 Copyright(cid:3)C2001byAcademicPress,Inc. Allrightsofreproductioninanyformreserved. 0065-3055/01$35.00

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