C-X bond formation

194 Pages·2010·1.87 MB·English

by  Kilian Muñiz (auth.)

31
Topics in Organometallic Chemistry
Editorial Board:
M. Beller J. M. Brown P. H. Dixneuf
l l
A. Fu¨rstner L. S. Hegedus P. Hofmann
l l
T. Ikariya L. A. Oro M. Reetz Q.-L. Zhou
l l l
Topics in Organometallic Chemistry
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C–X Bond Formation
Volume Editor: Arkadi Vigalok
With Contributions by
(cid:1) (cid:1) (cid:1)
Paul Bichler Moris S. Eisen David S. Glueck
(cid:1) (cid:1) (cid:1)
Lukas Hintermann Ariela W. Kaspi Jennifer A. Love
Kilian Mun˜iz (cid:1) Andrei N. Vedernikov (cid:1) Arkadi Vigalok
Editor
Prof.ArkadiVigalok
SchoolofChemistry
TheSacklerFacultyofExactSciences
TelAvivUniversity
TelAviv69978
Israel
[email protected]
ISSN1436-6002 e-ISSN1616-8534
ISBN978-3-642-12072-5 e-ISBN978-3-642-12073-2
DOI10.1007/978-3-642-12073-2
SpringerHeidelbergDordrechtLondonNewYork
LibraryofCongressControlNumber:2010926024
#Springer-VerlagBerlinHeidelberg2010
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Volume Editor
Prof.ArkadiVigalok
SchoolofChemistry
TheSacklerFacultyofExactSciences
TelAvivUniversity
TelAviv69978
Israel
[email protected]
Editorial Board
Prof.MatthiasBeller Prof.PeterHofmann
Leibniz-Institutfu¨rKatalysee.V. Organisch-ChemischesInstitut
anderUniversita¨tRostock Universita¨tHeidelberg
Albert-Einstein-Str.29a ImNeuenheimerFeld270
18059Rostock,Germany 69120Heidelberg,Germany
[email protected] [email protected]
Prof.JohnM.Brown Prof.TakaoIkariya
ChemistryResearchLaboratory DepartmentofAppliedChemistry
OxfordUniversity GraduateSchoolofScienceandEngineering
MansfieldRd., TokyoInstituteofTechnology
OxfordOX13TA,UK 2-12-1Ookayama,Meguro-ku,
[email protected] Tokyo152-8550,Japan
[email protected]
Prof.PierreH.Dixneuf
Prof.LuisA.Oro
CampusdeBeaulieu
Universite´deRennes1 InstitutoUniversitariodeCata´lisisHomoge´nea
Av.duGlLeclerc DepartmentofInorganicChemistry
35042RennesCedex,France I.C.M.A.-FacultyofScience
[email protected] UniversityofZaragoza-CSIC
Zaragoza-50009,Spain
Prof.AloisFu¨rstner [email protected]
Max-Planck-Institutfu¨rKohlenforschung Prof.ManfredReetz
Kaiser-Wilhelm-Platz1
Max-Planck-Institutfu¨rKohlenforschung
45470Mu¨lheimanderRuhr,Germany
Kaiser-Wilhelm-Platz1
[email protected]
45470Mu¨lheimanderRuhr,Germany
Prof.LouisS.Hegedus [email protected]
DepartmentofChemistry Prof.Qi-LinZhou
ColoradoStateUniversity
StateKeyLaboratoryofElemento-organic
FortCollins,Colorado80523-1872,USA
Chemistry
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NankaiUniversity
WeijinRd.94,Tianjin300071PRChina
[email protected]
v
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vii
Preface
Reactions resulting in the formation of C–X bonds were undoubtedly among the
firstexperimentsperformedbysyntheticorganicchemists.Withyears,thisareaof
research hasmatured and nowadays reliesheavilyon the useoftransition metals.
MostoftherecentresearchinC–Xbond-formingreactionshasbeenfocusedonthe
late transition metal-catalyzed formation of aryl-nitrogen and aryl-oxygen bonds,
reactions of primary importance to the pharmaceutical industry. Many highly
efficient catalytic systems allowing for the formation of these bonds under mild
conditionshavebeendevelopedandthoroughlyreviewed.Againstthisbackground,
other C–X bond-forming reactions received considerably less attention. This
volume is intended to highlight the recent advances in the formation of the C–X
bondsotherthanaryl-oxygenoraryl-nitrogen.
While not comprehensive, it presents seven balanced chapters that summarize
the synthetic and mechanistic studies of the formation of C–P, C–S, C–Halide,
C–N, and C–O bonds. The reviewed research areas demonstrate great variety of
metals and reaction mechanisms that can be involved in the formation of these
bonds. I believe that this scope will only grow in the near future thus providing
importantinformationforchemistsinterestedinmakingC–Xbonds.
As editor, I wish to express my gratitude to all the experts who contributed to
thisvolume.
TelAviv ArkadiVigalok
ix
Contents
TransitionMetalCatalyzedElectrophilicHalogenation
ofC–HBondsinAlpha-PositiontoCarbonylGroups ...................... 1
KilianMun˜iz
LateTransitionMetal-MediatedFormationofCarbon–Halogen
Bonds ........................................................................... 19
ArkadiVigalokandArielaW.Kaspi
OrganometallicApproachestoCarbon–SulfurBondFormation ......... 39
PaulBichlerandJenniferA.Love
RecentAdvancesinMetal-CatalyzedC–PBondFormation .............. 65
DavidS.Glueck
C–OReductiveEliminationfromHighValentPtandPdCenters ...... 101
AndreiN.Vedernikov
RecentDevelopmentsinMetal-CatalyzedAdditionsofOxygen
NucleophilestoAlkenesandAlkynes ....................................... 123
LukasHintermann
CatalyticC–N,C–O,andC–SBondFormationPromoted
byOrganoactinideComplexes .............................................. 157
MorisS.Eisen
Index .......................................................................... 185
xi
TopOrganometChem(2010)31:1–18
DOI10.1007/978-3-642-12073-2_1
#Springer-VerlagBerlinHeidelberg2010
Transition Metal Catalyzed Electrophilic
Halogenation of C–H Bonds in Alpha-Position
to Carbonyl Groups
KilianMun˜iz
Abstract Transition metalsbearing chiral nonracemic ligands can actasefficient
catalystsfortheselectivea-halogenationnexttocarbonylgroupsinorganicmole-
cules. As a general reaction pattern, many of these reactions make use of 1,3-
dicarbonyl or related functionalization readily, leading to enolization upon an
interaction with Lewis acidic metal catalysts. Subsequent reaction with electro-
philic halogenating reagents establishes the formation of new carbon-halogen
bonds with asymmetric induction. This chapter discusses the state of the art of
thesereactions,includingmechanisticdetailsregardingcatalyticcyclesandmodels
for stereoselection. It also includes recent progresses on substrates other than
1,3-dicarbonyls,selectivemonohalogenationofmethylenegroupsandnewmecha-
nisticpathways,suchastheuseofnucleophilicfluorinesources.
Keywords Carbonyl compounds (cid:1) Catalysis (cid:1) Electrophilic substitution (cid:1)
Halogenation(cid:1)Transitionmetals
Contents
1 Introduction ................................................................................. 2
2 TransitionMetalCatalysts .................................................................. 3
2.1 TitaniumCatalysts .................................................................... 3
2.2 PalladiumCatalysts ................................................................... 6
2.3 NickelCatalysts...................................................................... 11
2.4 RutheniumCatalysts ................................................................. 14
2.5 OtherMetalCatalysts ................................................................ 15
3 Conclusion .................................................................................17
References ......................................................................................17
K.Mun˜iz
Catalonian Institute for Chemical Investigation (ICIQ), Av. Pa¨ısos Catalans 16, Tarragona
E-43007,Spain
e-mail:[email protected]