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Iridium Complexes in Organic Synthesis

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Iridium Complexes in Organic Synthesis

Luis A. Oro (Editor), Carmen Claver (Editor)

ISBN: 978-3-527-31996-1 December 2008 424 Pages

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Description

Ranging from hydrogenation to hydroamination, cycloadditions and nanoparticles, this first handbook to comprehensively cover the topic of iridium in synthesis discusses the important advances in iridium-catalyzed reactions, namely the use of iridium complexes in enantioselective catalysis.
A must for organic, complex and catalytic chemists, as well as those working with/on organometallics.
APPLICATION OF IRIDIUM CATALYSTS IN THE FINE CHEMICALS INDUSTRY
Introduction
Industrial Requirements for Applying Catalysts
Enantioselective Hydrogenation of C=N Bonds
Enantioselective Hydrogenation of C=C Bonds
Miscellaneous Catalytic Applications with Industrial Potential
DIHYDRIDO IRIDIUM TRIISOPROPYLPHOSPHINE COMPLEXES: FROM ORGANOMETALLIC CHEMISTRY TO CATALYSIS
Introduction
[Ir(COD)(NCMe)(PR3)]BF4 (PR=PiPr3, PMe3) and Related Complexes as Catalyst Precursors: Is 1,5-Cyclo-Octadiene an Innocent and Removable Ligand?
The Dihydrido Iridium Triisopropylphosphine Complex [IrH2(NCMe)3(PiPr3)]BF4 as Alkene Hydrogenation Catalysts
The Dihydrido Iridium Triisoprpylphosphine Complex [IrH2(NCMe)3(PiPr3)]BF4 as Alkyne Hydrogenation Catalysts
Dihydrido Arene Iridium Triisopropylphosphine Complexes
Dihydrido Iridium Triisopropylphosphine Complexes as Imine Hydrogenation Catalysts
IRIDIUM N-HETEROCYCLIC CARBENE COMPLEXES AND THEIR APPLICATON AS HOMOGENEOUS CATALYSTS
Introduction
Types or Ir-NHC and Reactivity
Catalysis with Ir-NHCs
IRIDIUM-CATALYZED C=O HYDROGENATION
Introduction
Homogeneous C=O Hydrogenations
Heterogeneous, Supported and Biocatalytic Hydrogenations
CATALYTIC ACTIVITY OF Cp* IRIDIUM COMPLEXES IN HYDROGEN TRANSFER REACTONS
Introduction
Hydrogen Transfer Oxidation of Alcohols (Oppenauer-Type Oxidation)
Transfer Hydrogenation of Unsaturated Compounds
Asymmetric Synthesis Based on Hydrogen Transfer
Hydrogen Transfer Reactions in Aqueous Media
Carbon-Nitrogen Bond Formation Based on Hydrogen Transfer
Carbon-Carbon Bond Formation Based on Hydrogen Transfer
Carbon-Oxygen Bond Formation Based on Hydrogen Transfer
Dehydrogenative Oxidation of Alcohols
IRIDIUM-CATALYZED HYDROAMINATION
Introduction
Iridium-Catalyzed Olefin Hydroamination (OHA)
Iridium-Catalyzed Alkyne Hydroamination (ASA)
Proposed Mechanisms
Complexes and Reactions of Ir Relevant to Hydroamination
IRIDIUM-CATALYZED BORON-ADDITION
Introduction
Iridium-Boryl Complexes
Hydroboration
Diboration
Borylation
IRIDIUM-CATALYZED METHANOL CARBONYLATION
Introduction
Rhodium-Based Processes
Iridium Reactivity in the Methanol Carbonylation Reaction
The Iridium-Based Cativa Process
The Iridium-Platinum-Based Process
The Iridium-Cocatalyst Mechanism, and Conclusion Acknowledgments
IRIDIUM-CATALYZED ASYMMETRIC ALLYLIC SUBSTITUTIONS
Introduction
Ir-Catalyzed Allylic Substitutions: Fundamentals
C-Nucleophiles
N-Nucleophiles
O-Nucleophiles
Synthesis of Biologically Active Compounds via Allylic Substitution
IRIDIUM-CATALYZED COUPLING REACTIONS
Introduction
Iridium-Catalyzed Dimerization and Cyclotrimerization of Alkynes
Iridium-Catalyzed, Three-Component Coupling Reactions of Aldehydes, Amines and Alkynes
Head-to-Tail Dimerization of Acrylates
A Novel Synthesis of Vinyl Ethers via an Unusual Exchange Reaction
Iridium-Catalyzed Allylic Substitution
Alkylation of Ketones with Alcohols
N-Alkylation of Amines
Oxidative Dimerization of Primary Alcohols to esters
Iridium-Catalyzed Addition of Water and Alcohols to Terminal Alkynes
Iridium-Catalyzed Direct Arylation of Aromatic C-H Bonds
Iridium-Catalyzed Anti-Markovnikov Olefin Arylation
Iridium-Catalyzed Silylation and Borylation of Aromatic C-H Bonds
Miscellaneous Reactions Catalyzed by Iridium Complexes
IRIDIUM-CATALYZED CYCLOADDITIONS
Introduction
[2+2+2] Cycloaddition
Enantioselective [2+2+2] Cycloaddition
[2+2+1] Cycloaddition
[4+2] and [5+1] Cycloaddition
Cycloisomerization
Ir(III)-Catalyzed Cyclizations
Miscellaneous Cycloadditions
PINCER-TYPE IRIDIUM COMPLEXES FOR ORGANIC TRANSFORMATIONS
Introduction
Iridium PCP-Catalyzed Activation of C(sp3)-H Bonds in Unfunctionalized Alkanes
Arene C(sp2)-H and Alyne C(sp1)-H Bond Activation
C-E Bond Activation
Ammonia Borane Dehydrogenation
IRIDIUM-MEDIATED ALKANE DEHYDROGENATION
Introduction
Alkane C-H Activation with Ir Derivatives
Alkane Dehydrogenation with Ir Complexes
Alkane Dehydrogenation Catalyzed by Ir Pincer Complexes
TRANSFORMATIONS OF (ORGANO)SILICON COMPOUNDS CATALYZED BY IRIDIUM COMPLEXES
Introduction
Hydrosilylation and Dehydrogenative Silylation of Carbon-Carbon Multiple Bonds
Asymmetric Hydrosilylation of Ketones and Imines
Transformation of Organosilicon Compounds in the Presence of Carbon Monoxide
Silylation of Aromatic Carbon-Hydrogen Bonds
Silylation of Alkenes with Vinylsilanes
Alcoholysis and Oxygenation of Hydrosilanes
Isomerization of Silyl Olefins
Addition of Silylacetglenes C-H Bonds into Imines
CATALYTIC PROPERTIES OF SOLUBLE IR IDIUM NANOPARTICLES
Introduction
Synthesis of Soluble Iridium Nanoparticles
Kinetic Studies of Iridium Nanoparticle Formation: The Autocatalytic Mechanism
Catalytic Applications of Soluble Iridium Nanoparticles

?This book provides good coverage of an increasingly important area and will be well worth reading by anyone interested in metal-catalyzed organic synthesis.? (The Journal of the American Chemical Society, July 2009)

?Both academic and industrial practitioners of transition-metal catalysis and organometallic chemistry will find this volume to be a very useful addition to their bookshelves.? ( Angewandte Chemie International Edition , June 2009)