Organometallics for Green Catalysis

309 Pages·2019·21.37 MB·English

by  Pierre H. Dixneuf

Topics in Organometallic Chemistry 63
Pierre H. Dixneuf
Jean-François Soulé Editors
Organometallics
for Green
Catalysis
63
Topics in Organometallic Chemistry
Editorial Board
M. Beller, Rostock, Germany
P. H. Dixneuf, Rennes, France
J. Dupont, Porto Alegre, Brazil
A. Fu¨rstner, Mu¨lheim, Germany
F. Glorius, Mu¨nster, Germany
L. J. Gooßen, Kaiserslautern, Germany
S. P. Nolan, Ghent, Belgium
J. Okuda, Aachen, Germany
L. A. Oro, Zaragoza, Spain
M. Willis, Oxford, United Kingdom
Q.-L. Zhou, Tianjin, China
Aims and Scope
TheseriesTopicsinOrganometallicChemistrypresentscriticaloverviewsofresearch
resultsinorganometallicchemistry.Asourunderstandingoforganometallicstructure,
properties and mechanisms increases, new ways are opened for the design of
organometalliccompoundsandreactionstailoredtotheneedsofsuchdiverseareas
asorganicsynthesis,medicalresearch,biologyandmaterialsscience.Thusthescope
of 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 Online First with an individual DOI.
Inreferences,TopicsinOrganometallicChemistryisabbreviatedasTopOrganomet
Chemandcitedasajournal.
Moreinformationaboutthisseriesathttp://www.springer.com/series/3418
Pierre H. Dixneuf (cid:129) Jean-Franc¸ois Soule´
Editors
Organometallics for Green
Catalysis
With contributions by
(cid:1) (cid:1) (cid:1) (cid:1)
M. Beller K. Beydoun C. Bruneau N. Chatani
(cid:1) (cid:1) (cid:1)
J. G. de Vries P. H. Dixneuf R. A. Farrar-Tobar
(cid:1) (cid:1) (cid:1) (cid:1)
C. Fischmeister M. F. Hertrich P. Hu W. D. Jones
(cid:1) (cid:1) (cid:1) (cid:1) (cid:1)
J.Klankermayer A.Lei W.Leitner Y.Liu D.Milstein
M. Schmitz (cid:1) M. V. Solmi (cid:1) J.-F. Soule´ (cid:1) S. Tin (cid:1) M. Tobisu (cid:1)
H. Yi
Editors
PierreH.Dixneuf Jean-Franc¸oisSoule´
Organome´talliques,mate´riauxetCatalyse Organome´talliques,mate´riauxetCatalyse
UnivRennes,CNRS,(UMR6226) UnivRennes,CNRS,(UMR6226)
InstitutSciencesChimiques InstitutSciencesChimiques
Rennes,France Rennes,France
ISSN1436-6002 ISSN1616-8534 (electronic)
TopicsinOrganometallicChemistry
ISBN978-3-030-10954-7 ISBN978-3-030-10955-4 (eBook)
https://doi.org/10.1007/978-3-030-10955-4
LibraryofCongressControlNumber:2019931921
©SpringerNatureSwitzerlandAG2019
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Preface
Climate change, resource depletion, and environmental protection create new
challenges for the scientific community. In order to maintain quality of life by
developing novel technologies and sciences, chemists have to find new catalytic
processes toward green and sustainable chemistry and to offer useful industrial
applications. One consensus already reached is thatorganometallic chemistry and
related catalysts constitute a strength in the development of green chemistry.
Indeed, organometallic catalysis plays a crucial role in straightforward access to
complex molecules and novel molecular materials with the discovery of unprece-
dentedreactivitiesandhasbeenapillarofindustrialchemistry.Whilebothenergy
andgreenchemistryfieldsarestillunderdevelopment,theemergenceofconcepts
andstrategiesbasedonorganometallicsthatcontributelastingvalueisbeginningto
beobserved.
This volume of Topics in Organometallic Chemistry is dedicated to giving an
overview of the most important aspects of the applications of transition metal
complexes in green chemistry, including the transformation of renewables and
the formation of bulk chemicals as well as some examples of the storage or
productionofenergy.
Developing new strategies to recycle carbon dioxide into useful resources is
becoming increasingly crucial. The valorization of carbon dioxide into useful
productsoritsuseasanenergycarriercannowbeachievedowingtothedevelop-
mentofnoveltransitionmetalcomplexes.Thefirstchapterofthisvolume,written
byBellerandHertrich,focusedonhydrogenationofcarbondioxideintomethanol,
which is one of the most important reactions related to the “methanol economy”
concept. The prospect of utilizing carbon dioxide as a C1 feedstock for synthetic
applications is also discussed in two chapters. Leitner et al. give an outline of
catalytic pathways to synthesize a variety of useful compounds on reactions of
carbondioxideasC1buildingblockwithsimplealkenes,whileKlankermayerand
Beydounsummarizetherecentapplicationsofcarbondioxidefortheformationof
v
vi Preface
C–N and C–O bonds within the syntheses of formamides, methyl amines, and
dialkoxymethanes.
Sustainableproductionofbulkchemicalsfromrenewablesisnotlimitedtothe
use of carbon dioxide as the valorization of bio-based raw materials is also an
importantgreencatalysisresearchtopic.Recentprogresswasmadeusingorgano-
metalliccatalysts.ThechapterbyBruneauandFischmeisterrevealsthestateofthe
art for the valorization of oils by olefin metathesis, where specific organometallic
catalysts are now performant to be used for low purity renewable materials trans-
formations.Amongrenewablesorbio-basedrawmaterials,phenolderivativeshave
attractedsignificantattentionasarenewablearomaticfeedstockfortheproduction
of organic compounds that are useful for our society. Chatani and Tobisu give a
comprehensiveoverviewofrecentadvancesintheareaofcatalytictransformations
of phenol derivatives via the activation of C(aryl)–O bonds of aryl esters, carba-
mates,ethers,aswellasphenols.
Pincer complexes have recently brought revolutions incatalysis and especially
in the way to generate and activate hydrogen, leading to new catalytic processes
with high TON never reached before. The contribution of Jones points out the
predominantroleoflow-costironpincercomplexesassustainablecatalystsforthe
hydrogenationanddehydrogenationreactionsofcommonorganiccompounds.By
contrast, Milstein and Hu, employing water instead of hazardous oxidants, reveal
theeco-friendlyoxidationofalcoholsintocarboxylicacidswiththeuseofcatalytic
amountofpincercomplexes.DeVriesetal.pointouttheadvantagesofhydrogen
transfer reactions as green and selective processes for the preparation of allylic
alcohols, which are versatile compounds useful in a large variety of industrial
processes.
C–H bond activation and functionalization, which is one of most useful eco-
friendly processes in organic synthesis, and recently presented in two volumes of
TopicsinOrganometallicChemistrybyDixneufandDoucet,cannowbeachieved
with the help of photoredox systems enabling valorization of sunlight as a clean
energysource.DixneufandSoule´giveanoverviewoftheadvantagesoftheuseof
photoredox systems for the formation of C–C bonds from C(sp2)–H bonds under
greenconditions,whereasLeietal.presentthecontributionofC–Hbondoxidation
usingvisiblelightfortheformationofC–OandC–Nbonds.
This volume of Topics in Organometallic Chemistry offers a versatile point of
view on the recent progress of organometallic catalysis for valorization of bulk
chemicalsintothehigh-valuedaily-lifeproductsand/orenergyvectorusinggreen
catalytic processes, which is of growing importance for academic and industrial
scientists. The green catalytic processes presented in this volume are likely to
highlight the profit brought by catalysis for a better environment but also to the
improved knowledge of teachers and students in this developing field. Many
catalyticprocessespresentedinthis volume willinitiatethe design ofnew organ-
ometallics as more efficient catalysts and find further applications attractive for
industryandeconomy.
Preface vii
Wearegratefultoallthecontributors,expertsinvariouscomplementaryfields,
whohavecontributedwithustocreatethismultiple-facetvolume.
We dedicate this volume to all chemists and students who are contributing to
discover new organometallic catalysts and new green and sustainable catalytic
processesincreasingscientificknowledgeforoursocietalprofit.
Rennes,France PierreH.Dixneuf
Rennes,France Jean-Franc¸oisSoule´
24September2018
Contents
Metal-CatalysedHydrogenationofCO intoMethanol. . . . . . . . . . . . . 1
2
MaximilianFranzHertrichandMatthiasBeller
CatalyticProcessesCombiningCO andAlkenesintoValue-Added
2
Chemicals. . . . . . . . . . . . . . . . . . . .. . . . . . . . . . . . . . . . . . . . . . . . .. . . 17
MarcSchmitz,MatildeV.Solmi,andWalterLeitner
RecentAdvancesonCO UtilizationasC1BuildingBlockinC-N
2
andC-OBondFormation. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 39
KassemBeydounandJu¨rgenKlankermayer
AlkeneMetathesisforTransformationsofRenewables. . . . . . . . . . . . . 77
ChristianBruneauandCe´dricFischmeister
Metal-CatalyzedAromaticC-OBondActivation/Transformation. . . . . 103
MamoruTobisuandNaotoChatani
Hydrogenation/DehydrogenationofUnsaturatedBondswithIron
PincerCatalysis. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 141
WilliamD.Jones
ConversionofAlcoholstoCarboxylatesUsingWaterandBasewith
H Liberation. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 175
2
PengHuandDavidMilstein
SelectiveTransferHydrogenationofα,β-UnsaturatedCarbonyl
Compounds. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 193
RonaldA.Farrar-Tobar,SergeyTin,andJohannesG.deVries
FunctionalizationofC(sp2)–HBondsofArenesandHeteroarenes
AssistedbyPhotoredoxCatalystsfortheC–CBondFormation. . . . . . 225
PierreH.DixneufandJean-Franc¸oisSoule´
ix
x Contents
GreenCross-CouplingUsingVisibleLightforC–OandC–NBond
Formation. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 267
HongYi,YichangLiu,andAiwenLei
Correctionto:FunctionalizationofC(sp2)–HBondsofArenesand
HeteroarenesAssistedbyPhotoredoxCatalystsfortheC–CBond
Formation. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 295
PierreH.DixneufandJean-Franc¸oisSoule´
Index. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 297