Organometallics as Catalysts in the Fine Chemical Industry

164 Pages·2012·3.13 MB·English

by  Johannes G. de Vries (auth.)

42
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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Organometallics as Catalysts
in the Fine Chemical Industry
(cid:1)
Volume Editors: Matthias Beller Hans-Ulrich Blaser
With Contributions by
(cid:1) (cid:1) (cid:1) (cid:1)
H.-U. Blaser C.-y. Chen C.J. Cobley J.G. de Vries
(cid:1) (cid:1) (cid:1) (cid:1)
P. Dupau I.N. Houpis A.F. Indolese B. Pugin
(cid:1) (cid:1)
P. Ryberg F. Spindler G.T. Whiteker
Editors
MatthiasBeller Hans-UlrichBlaser
Universita¨tRostock ScientificAdvisor
Leibniz-Institutfu¨rOrganischeKatalyse SolviasAG
Rostock Basel
Germany Switzerland
ISBN978-3-642-32832-9 ISBN978-3-642-32833-6(eBook)
DOI10.1007/978-3-642-32833-6
SpringerHeidelbergNewYorkDordrechtLondon
LibraryofCongressControlNumber:2012945424
#Springer-VerlagBerlinHeidelberg2012
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Volume Editors
Prof.Dr.MatthiasBeller Dr.Hans-UlrichBlaser
Universita¨tRostock ScientificAdvisor
Leibniz-Institutfu¨rOrganischeKatalyse SolviasAG
Rostock Basel
Germany Switzerland
[email protected] [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]
.
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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
Although organometallic catalysts have been used on a large scale for the manu-
facture of bulk chemicals for many years, their application in the fine chemicals
industry is more recent. Despite the high impact of homogeneous catalysts on
organic chemistry, highlighted by three Nobel Prizes in the last decade, their
application for the industrial synthesis of more complex molecules is growing
rather slowly. The main purpose of this volume is to illustrate the potential of
organometalliccatalysisforthemanufactureofintermediatesandproductsasthey
areencounteredinthefinechemicals,agrochemicals,orpharmaceuticalsindustry.
The focus is on realized industrial applications described exclusively by authors
experienced with concrete, “real-world” synthetic challenges. Discussed are pro-
blems thatcan arisewhenmorecomplex,multifunctionalsubstratesare involved,
aswellassuccessfulapproachestotackletheseproblems.
Thevariouschaptersdemonstratetoorganicchemistsworkinginprocessdesign
and development that organometallic catalysis is not just an academic toy, but is
really a suitable tool for the large-scale production of complex intermediates.
Thebookwillhopefullyalsoserveasasourceofinformationandprovideinspira-
tionforacademicresearchers.
Thebookconsistsoftwotypesofcontributions,overviewchaptersonselected
technologiesandcasestudies.Consideringthatpublishingisnotatoppriorityfor
industrialscientists,weareveryhappythatwecouldfindcompetentauthorsinboth
categories.
The technology chapters cover the most important reaction types used in the
industry:JohannesG.deVries(DSM)givesanoverviewon“Palladium-Catalysed
Coupling Reactions”; Gregory T. Whiteker (Dow AgroSciences) and Christopher
J. Cobley (Chirotech Technology) review “Applications of Rhodium-Catalyzed
HydroformylationinthePharmaceutical,AgrochemicalandFragranceIndustries”;
PhilippeDupau(Firmenich)describesthe“Ruthenium-CatalyzedSelectiveHydro-
genation for Flavor and Fragrance Applications”; and Hans-Ulrich Blaser, Benoˆıt
Pugin, and Felix Spindler (Solvias) have authored the chapter on “Asymmetric
Hydrogenation.”
ix
x Preface
Case studies have been written by Ioannis Houpis (Janssen Pharmaceutica)
on “Sequential Pd-catalyzed Cross Coupling Reactions; Challenges on Scale-up,”
byAdrianoF.Indolese(RohnerChem)on“PilotPlantScaleSynthesisofanAryl-
indole – Scale up of a Suzuki Coupling,” by Per Ryberg (AstraZeneca) on the
“Development of a Mild and Robust Method for Palladium Catalysed Cyanation
on Large Scale,” and by Cheng-yi Chen (Merck Research Laboratories) on the
“Application of Ring Closing Metathesis Strategy to the Synthesis of Vaniprevir
(MK-7009),a20-MemberedMacrocyclicHCVProteaseInhibitor.”
Wethankalltheauthorsfortheireffortsandwehopethatourreadersfindtheir
contributionsenlightening.
Rostock,Germany MatthiasBeller
Basel,Switzerland Hans-UlrichBlaser