Table Of Content37
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
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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
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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
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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
