Iridium Complexes in Organic Synthesis:
"Ranging from mechanistic studies to industrial applications, this handbook is the first to comprehensively explore the topic of iridium in organic synthesis. The important advances in iridium mediated reactions namely hydrogenation, hydroamination, hydroboration, C-C bond formation, carbonylat...
Saved in:
| Other Authors: | , |
|---|---|
| Format: | Book |
| Language: | English |
| Published: |
Weinheim, Bergstr
WILEY-VCH
2009
|
| Edition: | 1. Aufl. |
| Subjects: | |
| Online Access: | Inhaltstext Inhaltsverzeichnis |
| Summary: | "Ranging from mechanistic studies to industrial applications, this handbook is the first to comprehensively explore the topic of iridium in organic synthesis. The important advances in iridium mediated reactions namely hydrogenation, hydroamination, hydroboration, C-C bond formation, carbonylation and cycloaddition are discussed. The book presents the most widely exploited iridium catalysed reactions, such as asymmetric reductions, together with the recent advances including the use of soluble metal nanoparticles as catalysts. In general terms, this book covers the application of iridium catalysts in organic synthesis from the more basic reactions to highlighted topics, including the use of specific ligands in the most important class of transition metal catalysed reactions."--BOOK JACKET. |
| Physical Description: | XVII, 396 S. Ill., graph. Darst. |
| ISBN: | 9783527319961 |
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MARC
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| 084 | |a CHE 376f |2 stub | ||
| 245 | 1 | 0 | |a Iridium Complexes in Organic Synthesis |c Hrsg. Luis A. Oro ; Hrsg. Carmen Claver |
| 250 | |a 1. Aufl. | ||
| 264 | 1 | |a Weinheim, Bergstr |b WILEY-VCH |c 2009 | |
| 300 | |a XVII, 396 S. |b Ill., graph. Darst. | ||
| 336 | |b txt |2 rdacontent | ||
| 337 | |b n |2 rdamedia | ||
| 338 | |b nc |2 rdacarrier | ||
| 520 | 1 | |a "Ranging from mechanistic studies to industrial applications, this handbook is the first to comprehensively explore the topic of iridium in organic synthesis. The important advances in iridium mediated reactions namely hydrogenation, hydroamination, hydroboration, C-C bond formation, carbonylation and cycloaddition are discussed. The book presents the most widely exploited iridium catalysed reactions, such as asymmetric reductions, together with the recent advances including the use of soluble metal nanoparticles as catalysts. In general terms, this book covers the application of iridium catalysts in organic synthesis from the more basic reactions to highlighted topics, including the use of specific ligands in the most important class of transition metal catalysed reactions."--BOOK JACKET. | |
| 650 | 4 | |a Asymmetric synthesis | |
| 650 | 4 | |a Iridium catalysts | |
| 650 | 4 | |a Organic compounds |x Synthesis | |
| 650 | 0 | 7 | |a Organische Synthese |0 (DE-588)4075695-6 |2 gnd |9 rswk-swf |
| 650 | 0 | 7 | |a Iridiumkomplexe |0 (DE-588)4223130-9 |2 gnd |9 rswk-swf |
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| 689 | 0 | 1 | |a Organische Synthese |0 (DE-588)4075695-6 |D s |
| 689 | 0 | |5 DE-604 | |
| 700 | 1 | |a Oro, Luis A. |4 edt | |
| 700 | 1 | |a Claver, Carmen |4 edt | |
| 856 | 4 | 2 | |q text/html |u http://deposit.dnb.de/cgi-bin/dokserv?id=3113105&prov=M&dok_var=1&dok_ext=htm |3 Inhaltstext |
| 856 | 4 | 2 | |m Digitalisierung UB Bayreuth |q application/pdf |u http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=016995446&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |3 Inhaltsverzeichnis |
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Contents
Preface XIII
List of Contributors XV
Ί
Application of
Iridium
Catalysts in the Fine Chemicals Industry
1
Hans-Ulrich Blaser
1.1
Introduction
1
1.2
Industrial Requirements for Applying Catalysts
1
1.2.1
Characteristics of the Manufacture of Enantiomerically Pure Products
1.2.2
Process Development: Critical Factors for the Application
of Catalysts
2
1.2.3
Requirements for Practically Useful Catalysts
3
1.2.3.1
Preparation Methods
3
1.2.3.2
Catalysts Cost
3
1.2.3.3
Availability of the Catalysts
3
1.2.3.4
Catalytic Performance
3
1.2.3.5
Separation
4
1.3
Enantioselective
Hydrogénation
of C=N Bonds
4
1.3.1
Catalysts and Scope
4
1.3.2
Industrial Applications
6
1.4
Enantioselective
Hydrogénation
of C=C Bonds
8
1.4.1
Catalysts and Scope
8
1.4.2
Industrial Applications
9
1.5
Miscellaneous Catalytic Applications with Industrial Potential
10
1.6
Conclusions and Outlook
13
References
13
2
Di
hyd
rido
Iridium Triisopropylphosphine Complexes:
From Organometallic Chemistry to Catalysis
15
Luis
A. Oro
2.1
Introduction
15
2.2
[IrţCODHNCMeXPRjpF,,
(PR3
=
Р'Ргз, РМе3)
and Related Complexes
as Catalyst Precursors: Is l.S-Cyclo-Octadiene an Innocent and
Removable Ligand?
16
Indium Complexes in Organic Synthesis. Edited by Luis
A. Oro
and Carmen Claver
Copyright
© 2009
WILEY-VCH
Verlag
GmbH
&
Co. KGaA,
Weinheim
ISBN:
978-3-527-31996-1
VI
Contents
2.3
The Dihydrido Iridium Triisopropylphosphine Complex
[IrH2(NCMe)3(P'Pr3)]BF4 as Alkene
Hydrogénation
Catalysts
21
2.4
The Dihydrido Iridium Triisopropylphosphine Complex
[IrH2(NCMe)3(P'Prj)]BF4 as Alkyne
Hydrogénation
Catalysts
26
2.5
Dihydrido
Arene
Iridium Triisopropylphosphine Complexes
29
2.6
Dihydrido Iridium Triisopropylphosphine Complexes as Imine
Hydrogénation
Catalysts
34
2.7
Conclusions
37
Acknowledgments
37
References
37
3
Iridium N-Heterocydic Carbene Complexes and Their Application as
Homogeneous Catalysts
39
Eduardo
Peris and Robert H. Crabtree
3.1
Introduction
39
3.2
Types of
Ir—NHC
and Reactivity
40
3.2.1
Mono-NHCs and Intramolecular
C—H
Activation
40
3.2.2
Chelating bis-NHCs
43
3.2.3
Abnormal NHCs
46
3.3
Catalysis with
Ir—
NHCs
49
3.4
Conclusions
52
References
52
4
Indium-Catalyzed C=O
Hydrogénation
55
Claudio
Bianchirli, Luca Consalvi and Maurizio Peruzzini
4.1
Introduction
55
4.2
Homogeneous C=O
Hydrogénations
55
4.2.1
Chemoselective
Hydrogénations
56
4.2.2
Enantioselective
Hydrogénations
63
4.2.3
Transfer
Hydrogénation
(TH)
69
4.2.4
Asymmetric Transfer
Hydrogénation
(ΑΤΗ)
81
4.3
Heterogeneous, Supported and Biocatalytic
Hydrogénations
99
References
103
5
Catalytic Activity of Cp* Iridium Complexes in Hydrogen
Transfer Reactions
107
Ken-ichi Fujita and Ryohei Yamaguchi
5.1
Introduction
107
5.2
Hydrogen Transfer Oxidation of Alcohols
(Oppenauer-Type Oxidation)
108
5.3
Transfer
Hydrogénation
of Unsaturated Compounds
112
5.3.1
Transfer
Hydrogénation
of Quinolines
112
5.3.2
Transfer
Hydrogénation
of Ketones and Imines
113
5.4
Asymmetric Synthesis Based on Hydrogen Transfer
113
5.4.1
Asymmetric Transfer
Hydrogénation
of Ketones
113
5.4.2
Dynamic Kinetic Resolution
118
Contents
VII
5.5
Hydrogen Transfer Reactions in Aqueous Media
119
5.6
Carbon-Nitrogen Bond Formation Based on Hydrogen Transfer
123
5.6.1
N-Alkylation of Amines with Alcohols
123
5.6.2
Cyclization of
Amino
Alcohols
126
5.6.3
Cyclization of Primary Amines with Diols
127
5.6.4
Amidation of Alcohols with Hydroxylamine
128
5.7
Carbon-Carbon Bond Formation Based on Hydrogen Transfer
130
5.7.1 ß-Alkylation
of Secondary Alcohols
130
5.7.2
Alkylation of Active
Methylene
Compounds with Alcohols
131
5.8
Carbon-Oxygen Bond Formation Based on Hydrogen Transfer
135
5.8.1
Oxidative Lactonization of Diols
135
5.8.2
Inter- and Intra-Molecular Tishchenko Reactions
137
5.9
Dehydrogenative Oxidation of Alcohols
138
5.10
Conclusions
240
References
140
6
Iridium-Catalyzed Hydroamination
145
Romano Dorta
6.1
Introduction
145
6.2
Iridium-Catalyzed
Olefin
Hydroamination
(ОНА)
346
6.2.1
The Ir(III)/Secondary Amines/Ethylene System
146
6.2.2
The IrflJ/ZnCb/Aniline/Norbornene System
146
6.2.3
The Chiral Ir(I)/'Naked Fluoride'/Norbornene/Aniline System
147
b.lA The Chiral IrflJ/Organic Base/Anilines/Olefins System
150
6.2.5
The Irflj/Piperidine/Methacrylonitrile System
151
6.3
Iridium-Catalyzed Alkyne Hydroamination (AHA)
152
6.3.1
Intramolecualar Aliphatic Systems
152
6.3.2
índoles
via Intramolecular AHA
153
6.3.3
Intermolecular Alkyne Hydroamination
253
6.4
Proposed Mechanisms
256
6.4.1
Olefin
Hydroamination
156
6.4.2
Alkyne Hydroamination
258
6.5
Complexes and Reactions of
Ir
Relevant to Hydroamination
260
6.5.1
Ir(I)-Amine Complexes
160
6.5.2
Ir(I)-Anilido complexes
161
6.5.3
Ν—Η
Bond Activation Leading to Ir(III)-Amido-Hydrido
Complexes
162
6.5.4
Alkyl-Amino-Hydrido Complexes of Ir(III)
165
6.5.5
Indium-Fluoride Complexes
168
6.6
Conclusions
169
References
2 70
7
Iridium-Catalyzed Boron-Addition
273
Elena
Fernández
and Anna M. Segarra
7.1
Introduction
173
7.2
Iridium-Boryl Complexes
273
VIII Contents
7.3 Hydroboration 176
7.4 Diboration 184
7.5 Borylation 185
References
191
8 Iridium-Catalyzed Methanol Carbonylation 195
Philippe Kalck and Philippe Serp
8.1
Introduction J
95
8.2
Rhodium-Based Processes
197
8.2.1
The Monsanto Process
197
8.2.2
The
Celanese
Process
199
8.3
Iridium Reactivity in the
Methanol
Carbonylation Reaction
200
8.4
The Iridium-Based
Cativa
Process
204
8.5
The Iridium-Platinum-Based Process
206
8.6
The Iridium-Cocatalyst Mechanism, and Conclusions
207
Acknowledgments
207
References
208
9
Iridium-Catalyzed Asymmetric Allylic Substitutions
211
Günter Helmchen
9.1
Introduction
211
9.2
Ir-Catalyzed Allylic Substitutions: Fundamentals
212
9.2.1
Reactivity and Regioselectivity
212
9.2.2
Steric Course
214
9.2.3
Asymmetric Catalysis: The Beginnings with Phosphinooxazolines as
Chiral Ligands
215
9.2.4
Phosphoramidites as Ligands for the Ir-Catalyzed
Allylic Substitution
216
9.2.4.1
Survey
216
9.2.4.2
Catalyst Preparation, Reaction Conditions and Catalytic Cycle
217
9.2.4.3
Preparation of Phosphoramidites
219
9.2.4.4
Variation of the Phosphoramidite Ligands
219
9.2.4.5
Further Ligands Used in Ir-Catalyzed Allylic Substitutions
220
9.3
C-Nucleophiles
221
9.3.1
Stabilized Enolates as Nucleophiles
221
9.3.1.1
Malonates and Related Pronucleophiles
221
9.3.2
Aliphatic
Nitro
Compounds as Pronucleophiles
224
9.3.2.1
A Glycine
Equivalent as Pronucleophile
225
9.3.3
Allylic Substitutions with Nonstabilized Enolates, Enamines and
Organozinc Compounds
226
9.3.3.1
Ketone
Enolates Derived from Silyl Enol Ethers as Nucleophiles
226
9.3.3.2
Allylation of Enamines
227
9.3.3.3
Decarboxylative Allylic Alkylation
227
9.3.3.4
Reactions with Aryl Zinc Compounds
228
9.4
N-Nucleophiles
229
Contents
IX
9.4.1
Inter- and Intramolecular Reactions with Aliphatic Amines and
Ammonia as Nucleophiles
229
9.4.2
Arylamines as Nucleophiles
232
9.4.3 Amination
of Allylic Alcohols
232
9.4.4
Pronucleophiles Serving as Ammonia Surrogates: N^N-Diacylamines,
Trifluoroacetamide and N-Sulfonylamines
233
9.4.5
Decarboxylative Allylic Amidation
236
9.4.6
Dihydropyrroles and
γ
-Lactams
via Allylic Substitution and Ring-
Closing Metathesis
237
9.4.7
Hydroxylamine Derivatives as N-Nucleophiles
238
9.5
O-Nucleophiles
239
9.5.1
Phenolates as Nucleophiles
239
9.5.2 Alkoxides
as Nucleophiles
241
9.5.3
Hydroxylamine Derivatives as O-Nucleophiles
242
9.5.4
Silanolates as Nucleophiles
242
9.5.5
Dihydrofurans via Allylic Etherification in Combination
with RCM
244
9.6
Synthesis of Biologically Active Compounds via Allylic
Substitution
244
9.7
Conclusions
246
Acknowledgments
247
References
247
10
Iridium-Catalyzed Coupling Reactions
251
Yasutaka Ishii, Yasushi
Obora
and Satoshi Sakaguchi
10.1
Introduction
251
10.2
Iridium-Catalyzed Dimerization and Cyclotrimerization
of Alkynes
251
10.3
Iridium-Catalyzed, Three-Component Coupling Reactions of
Aldehydes, Amines and Alkynes
253
10.4
Head-to-Tail
Dimerization of Acrylates
256
10.5
A Novel Synthesis of Vinyl Ethers via an Unusual
Exchange Reaction
258
10.6
Iridium-Catalyzed Allylic Substitution
260
10.7
Alkylation of Ketones with Alcohols
262
10.8
N-Alkylation of Amines
264
10.9
Oxidative Dimerization of Primary Alcohols to Esters
266
10.10
Iridium-Catalyzed Addition of Water and Alcohols to
Terminal Alkynes
266
10.11
Iridium-Catalyzed Direct Arylation of Aromatic
C—H
Bonds
267
10.12
Iridium-Catalyzed Anti-Markovnikov
Olefin
Arylation
267
10.13
Iridium-Catalyzed Silylation and Borylation of Aromatic
C—H
Bonds
268
10.14
Miscellaneous Reactions Catalyzed by
Iridium
Complexes
269
References
271
X
Contents
Π
Iridium-Catalyzed Cycloadditions
277
Takanori Shibata
11.1
Introduction
277
11.2 [2+2+2]
Cycloaddition
278
11.3
Enantioselective
[2+2+2]
Cycloaddition
281
11.4 [2+2+1]
Cycloaddition
283
11.5 [4+2]
and
[5+1]
Cycloadditions
288
11.6
Cycloisomerization
289
11.7
Ir(III)-Catalyzed Cyclizations
291
11.8
Miscellaneous
Cycloadditions
293
11.9
Conclusions
295
References
296
12
Pincer-Type Iridium Complexes
for Organic
Transformations
299
Martin
Albrecht
and David Morales-Morales
12.1
Introduction
299
12.2
Iridium
PCP-Catalyzed Activation of
C(sp3)—H Bonds in
Unfunctionalized Alkanes
300
12.2.1
Scope of the Reaction
300
12.2.2
Mechanistic Considerations
302
12.2.3
Catalyst Optimization
307
12.2.4
Application of Alkane Functionalization
309
12.2.4.1
Alkane Metathesis
309
12.2.4.2
Polymer Functionalization
310
12.3
Arene
C(sp2)—
H
and Alkyne Cfsp1)—
H
Bond Activation
311
12.3.1
Activation of Qsp2)—
H
Bonds
312
12.3.2
Activation of Cfsp1)—
H
Bonds
315
12
A C—E
Bond Activation
317
12.4.1
Activation of Carbon-Halogen Bonds
317
12.4.2
Activation of Carbon-Oxygen Bonds
318
12.4.3
Activation of Carbon-Carbon Bonds
318
12.5
Ammonia
Borane
Dehydrogenation
319
12.6
Conclusions
321
Acknowledgments
321
References
321
13
Indium-Mediated Alkane Dehydrogenation
325
David Morales-Morales
13.1
Introduction
325
13.1.1
The Beginning
326
13.2
Alkane
C—H
Activation with
Ir
Derivatives
327
13.3
Alkane Dehydrogenation with
Ir
Complexes
328
13.4
Alkane Dehydrogenation Catalyzed by
Ir
Pincer
Complexes
333
ПАЛ
Ir-PCP
Pincer
Compounds
333
13.4.2
Ir-POCOP
Pincer
Compounds
336
Contents
XI
13.5 Final
Remarks
342
Acknowledgments
342
References
342
Ί4
Transformations of (Organojsilicon Compounds Catalyzed by Indium
Complexes
345
Bogdan Marciniec
and
Ireneusz Kownacki
14.1
Introduction
345
14.2
Hydrosilylation and Dehydrogenative Silylation of Carbon-Carbon
Multiple Bonds
346
14.2.1
Hydrosilylation and Dehydrogenative Silylation of Alkenes
346
14.2.2
Application of Hydrosilylation in Polymer Chemistry
348
14.2.3
Hydrosilylation and Dehydrogenative Silylation of Alkynes
349
14.3
Asymmetric Hydrosilylation of Ketones and Imines
352
14.4
Transformation of Organosilicon Compounds in the Presence of
Carbon Monoxide
356
14.4.1
Hydroformylation of Vinylsilanes
356
14.4.2
Silylcarbonylation of Alkenes and Alkynes
357
14.5
Silylation of Aromatic Carbon-Hydrogen Bonds
359
14.6
Silylation of Alkenes with Vinylsilanes
360
14.7
Alcoholysis and
Oxygénation
of Hydrosilanes
362
14.8
Isomerization of Silyl Olefins
362
14.9
Addition of silylacetglenes sC—
H
Bonds into Imines
362
14.10
Conclusions
364
References
365
15
Catalytic Properties of Soluble
Iridium Nanoparticles
369
Jackson D.
Scholten
andjaïrton Dupont
15.1
Introduction
369
15.2
Synthesis of Soluble Iridium Nanoparticles
369
15.2.1
Polyoxoanions
369
15.2.2
Surfactants
370
15.2.3
Imidazolium Ionic Liquids
372
15.3
Kinetic Studies of Iridium Nanoparticle Formation:
The Autocatalytic Mechanism
377
15.4
Catalytic Applications of Soluble Iridium Nanoparticles
380
15.5
Conclusions
387
References
388
Index
391 |
| adam_txt |
Contents
Preface XIII
List of Contributors XV
Ί
Application of
Iridium
Catalysts in the Fine Chemicals Industry
1
Hans-Ulrich Blaser
1.1
Introduction
1
1.2
Industrial Requirements for Applying Catalysts
1
1.2.1
Characteristics of the Manufacture of Enantiomerically Pure Products
1.2.2
Process Development: Critical Factors for the Application
of Catalysts
2
1.2.3
Requirements for Practically Useful Catalysts
3
1.2.3.1
Preparation Methods
3
1.2.3.2
Catalysts Cost
3
1.2.3.3
Availability of the Catalysts
3
1.2.3.4
Catalytic Performance
3
1.2.3.5
Separation
4
1.3
Enantioselective
Hydrogénation
of C=N Bonds
4
1.3.1
Catalysts and Scope
4
1.3.2
Industrial Applications
6
1.4
Enantioselective
Hydrogénation
of C=C Bonds
8
1.4.1
Catalysts and Scope
8
1.4.2
Industrial Applications
9
1.5
Miscellaneous Catalytic Applications with Industrial Potential
10
1.6
Conclusions and Outlook
13
References
13
2
Di
hyd
rido
Iridium Triisopropylphosphine Complexes:
From Organometallic Chemistry to Catalysis
15
Luis
A. Oro
2.1
Introduction
15
2.2
[IrţCODHNCMeXPRjpF,,
(PR3
=
Р'Ргз, РМе3)
and Related Complexes
as Catalyst Precursors: Is l.S-Cyclo-Octadiene an Innocent and
Removable Ligand?
16
Indium Complexes in Organic Synthesis. Edited by Luis
A. Oro
and Carmen Claver
Copyright
© 2009
WILEY-VCH
Verlag
GmbH
&
Co. KGaA,
Weinheim
ISBN:
978-3-527-31996-1
VI
Contents
2.3
The Dihydrido Iridium Triisopropylphosphine Complex
[IrH2(NCMe)3(P'Pr3)]BF4 as Alkene
Hydrogénation
Catalysts
21
2.4
The Dihydrido Iridium Triisopropylphosphine Complex
[IrH2(NCMe)3(P'Prj)]BF4 as Alkyne
Hydrogénation
Catalysts
26
2.5
Dihydrido
Arene
Iridium Triisopropylphosphine Complexes
29
2.6
Dihydrido Iridium Triisopropylphosphine Complexes as Imine
Hydrogénation
Catalysts
34
2.7
Conclusions
37
Acknowledgments
37
References
37
3
Iridium N-Heterocydic Carbene Complexes and Their Application as
Homogeneous Catalysts
39
Eduardo
Peris and Robert H. Crabtree
3.1
Introduction
39
3.2
Types of
Ir—NHC
and Reactivity
40
3.2.1
Mono-NHCs and Intramolecular
C—H
Activation
40
3.2.2
Chelating bis-NHCs
43
3.2.3
Abnormal NHCs
46
3.3
Catalysis with
Ir—
NHCs
49
3.4
Conclusions
52
References
52
4
Indium-Catalyzed C=O
Hydrogénation
55
Claudio
Bianchirli, Luca Consalvi and Maurizio Peruzzini
4.1
Introduction
55
4.2
Homogeneous C=O
Hydrogénations
55
4.2.1
Chemoselective
Hydrogénations
56
4.2.2
Enantioselective
Hydrogénations
63
4.2.3
Transfer
Hydrogénation
(TH)
69
4.2.4
Asymmetric Transfer
Hydrogénation
(ΑΤΗ)
81
4.3
Heterogeneous, Supported and Biocatalytic
Hydrogénations
99
References
103
5
Catalytic Activity of Cp* Iridium Complexes in Hydrogen
Transfer Reactions
107
Ken-ichi Fujita and Ryohei Yamaguchi
5.1
Introduction
107
5.2
Hydrogen Transfer Oxidation of Alcohols
(Oppenauer-Type Oxidation)
108
5.3
Transfer
Hydrogénation
of Unsaturated Compounds
112
5.3.1
Transfer
Hydrogénation
of Quinolines
112
5.3.2
Transfer
Hydrogénation
of Ketones and Imines
113
5.4
Asymmetric Synthesis Based on Hydrogen Transfer
113
5.4.1
Asymmetric Transfer
Hydrogénation
of Ketones
113
5.4.2
Dynamic Kinetic Resolution
118
Contents
VII
5.5
Hydrogen Transfer Reactions in Aqueous Media
119
5.6
Carbon-Nitrogen Bond Formation Based on Hydrogen Transfer
123
5.6.1
N-Alkylation of Amines with Alcohols
123
5.6.2
Cyclization of
Amino
Alcohols
126
5.6.3
Cyclization of Primary Amines with Diols
127
5.6.4
Amidation of Alcohols with Hydroxylamine
128
5.7
Carbon-Carbon Bond Formation Based on Hydrogen Transfer
130
5.7.1 ß-Alkylation
of Secondary Alcohols
130
5.7.2
Alkylation of Active
Methylene
Compounds with Alcohols
131
5.8
Carbon-Oxygen Bond Formation Based on Hydrogen Transfer
135
5.8.1
Oxidative Lactonization of Diols
135
5.8.2
Inter- and Intra-Molecular Tishchenko Reactions
137
5.9
Dehydrogenative Oxidation of Alcohols
138
5.10
Conclusions
240
References
140
6
Iridium-Catalyzed Hydroamination
145
Romano Dorta
6.1
Introduction
145
6.2
Iridium-Catalyzed
Olefin
Hydroamination
(ОНА)
346
6.2.1
The Ir(III)/Secondary Amines/Ethylene System
146
6.2.2
The IrflJ/ZnCb/Aniline/Norbornene System
146
6.2.3
The Chiral Ir(I)/'Naked Fluoride'/Norbornene/Aniline System
147
b.lA The Chiral IrflJ/Organic Base/Anilines/Olefins System
150
6.2.5
The Irflj/Piperidine/Methacrylonitrile System
151
6.3
Iridium-Catalyzed Alkyne Hydroamination (AHA)
152
6.3.1
Intramolecualar Aliphatic Systems
152
6.3.2
índoles
via Intramolecular AHA
153
6.3.3
Intermolecular Alkyne Hydroamination
253
6.4
Proposed Mechanisms
256
6.4.1
Olefin
Hydroamination
156
6.4.2
Alkyne Hydroamination
258
6.5
Complexes and Reactions of
Ir
Relevant to Hydroamination
260
6.5.1
Ir(I)-Amine Complexes
160
6.5.2
Ir(I)-Anilido complexes
161
6.5.3
Ν—Η
Bond Activation Leading to Ir(III)-Amido-Hydrido
Complexes
162
6.5.4
Alkyl-Amino-Hydrido Complexes of Ir(III)
165
6.5.5
Indium-Fluoride Complexes
168
6.6
Conclusions
169
References
2 70
7
Iridium-Catalyzed Boron-Addition
273
Elena
Fernández
and Anna M. Segarra
7.1
Introduction
173
7.2
Iridium-Boryl Complexes
273
VIII Contents
7.3 Hydroboration 176
7.4 Diboration 184
7.5 Borylation 185
References
191
8 Iridium-Catalyzed Methanol Carbonylation 195
Philippe Kalck and Philippe Serp
8.1
Introduction J
95
8.2
Rhodium-Based Processes
197
8.2.1
The Monsanto Process
197
8.2.2
The
Celanese
Process
199
8.3
Iridium Reactivity in the
Methanol
Carbonylation Reaction
200
8.4
The Iridium-Based
Cativa
Process
204
8.5
The Iridium-Platinum-Based Process
206
8.6
The Iridium-Cocatalyst Mechanism, and Conclusions
207
Acknowledgments
207
References
208
9
Iridium-Catalyzed Asymmetric Allylic Substitutions
211
Günter Helmchen
9.1
Introduction
211
9.2
Ir-Catalyzed Allylic Substitutions: Fundamentals
212
9.2.1
Reactivity and Regioselectivity
212
9.2.2
Steric Course
214
9.2.3
Asymmetric Catalysis: The Beginnings with Phosphinooxazolines as
Chiral Ligands
215
9.2.4
Phosphoramidites as Ligands for the Ir-Catalyzed
Allylic Substitution
216
9.2.4.1
Survey
216
9.2.4.2
Catalyst Preparation, Reaction Conditions and Catalytic Cycle
217
9.2.4.3
Preparation of Phosphoramidites
219
9.2.4.4
Variation of the Phosphoramidite Ligands
219
9.2.4.5
Further Ligands Used in Ir-Catalyzed Allylic Substitutions
220
9.3
C-Nucleophiles
221
9.3.1
Stabilized Enolates as Nucleophiles
221
9.3.1.1
Malonates and Related Pronucleophiles
221
9.3.2
Aliphatic
Nitro
Compounds as Pronucleophiles
224
9.3.2.1
A Glycine
Equivalent as Pronucleophile
225
9.3.3
Allylic Substitutions with Nonstabilized Enolates, Enamines and
Organozinc Compounds
226
9.3.3.1
Ketone
Enolates Derived from Silyl Enol Ethers as Nucleophiles
226
9.3.3.2
Allylation of Enamines
227
9.3.3.3
Decarboxylative Allylic Alkylation
227
9.3.3.4
Reactions with Aryl Zinc Compounds
228
9.4
N-Nucleophiles
229
Contents
IX
9.4.1
Inter- and Intramolecular Reactions with Aliphatic Amines and
Ammonia as Nucleophiles
229
9.4.2
Arylamines as Nucleophiles
232
9.4.3 Amination
of Allylic Alcohols
232
9.4.4
Pronucleophiles Serving as Ammonia Surrogates: N^N-Diacylamines,
Trifluoroacetamide and N-Sulfonylamines
233
9.4.5
Decarboxylative Allylic Amidation
236
9.4.6
Dihydropyrroles and
γ
-Lactams
via Allylic Substitution and Ring-
Closing Metathesis
237
9.4.7
Hydroxylamine Derivatives as N-Nucleophiles
238
9.5
O-Nucleophiles
239
9.5.1
Phenolates as Nucleophiles
239
9.5.2 Alkoxides
as Nucleophiles
241
9.5.3
Hydroxylamine Derivatives as O-Nucleophiles
242
9.5.4
Silanolates as Nucleophiles
242
9.5.5
Dihydrofurans via Allylic Etherification in Combination
with RCM
244
9.6
Synthesis of Biologically Active Compounds via Allylic
Substitution
244
9.7
Conclusions
246
Acknowledgments
247
References
247
10
Iridium-Catalyzed Coupling Reactions
251
Yasutaka Ishii, Yasushi
Obora
and Satoshi Sakaguchi
10.1
Introduction
251
10.2
Iridium-Catalyzed Dimerization and Cyclotrimerization
of Alkynes
251
10.3
Iridium-Catalyzed, Three-Component Coupling Reactions of
Aldehydes, Amines and Alkynes
253
10.4
Head-to-Tail
Dimerization of Acrylates
256
10.5
A Novel Synthesis of Vinyl Ethers via an Unusual
Exchange Reaction
258
10.6
Iridium-Catalyzed Allylic Substitution
260
10.7
Alkylation of Ketones with Alcohols
262
10.8
N-Alkylation of Amines
264
10.9
Oxidative Dimerization of Primary Alcohols to Esters
266
10.10
Iridium-Catalyzed Addition of Water and Alcohols to
Terminal Alkynes
266
10.11
Iridium-Catalyzed Direct Arylation of Aromatic
C—H
Bonds
267
10.12
Iridium-Catalyzed Anti-Markovnikov
Olefin
Arylation
267
10.13
Iridium-Catalyzed Silylation and Borylation of Aromatic
C—H
Bonds
268
10.14
Miscellaneous Reactions Catalyzed by
Iridium
Complexes
269
References
271
X
Contents
Π
Iridium-Catalyzed Cycloadditions
277
Takanori Shibata
11.1
Introduction
277
11.2 [2+2+2]
Cycloaddition
278
11.3
Enantioselective
[2+2+2]
Cycloaddition
281
11.4 [2+2+1]
Cycloaddition
283
11.5 [4+2]
and
[5+1]
Cycloadditions
288
11.6
Cycloisomerization
289
11.7
Ir(III)-Catalyzed Cyclizations
291
11.8
Miscellaneous
Cycloadditions
293
11.9
Conclusions
295
References
296
12
Pincer-Type Iridium Complexes
for Organic
Transformations
299
Martin
Albrecht
and David Morales-Morales
12.1
Introduction
299
12.2
Iridium
PCP-Catalyzed Activation of
C(sp3)—H Bonds in
Unfunctionalized Alkanes
300
12.2.1
Scope of the Reaction
300
12.2.2
Mechanistic Considerations
302
12.2.3
Catalyst Optimization
307
12.2.4
Application of Alkane Functionalization
309
12.2.4.1
Alkane Metathesis
309
12.2.4.2
Polymer Functionalization
310
12.3
Arene
C(sp2)—
H
and Alkyne Cfsp1)—
H
Bond Activation
311
12.3.1
Activation of Qsp2)—
H
Bonds
312
12.3.2
Activation of Cfsp1)—
H
Bonds
315
12
A C—E
Bond Activation
317
12.4.1
Activation of Carbon-Halogen Bonds
317
12.4.2
Activation of Carbon-Oxygen Bonds
318
12.4.3
Activation of Carbon-Carbon Bonds
318
12.5
Ammonia
Borane
Dehydrogenation
319
12.6
Conclusions
321
Acknowledgments
321
References
321
13
Indium-Mediated Alkane Dehydrogenation
325
David Morales-Morales
13.1
Introduction
325
13.1.1
The Beginning
326
13.2
Alkane
C—H
Activation with
Ir
Derivatives
327
13.3
Alkane Dehydrogenation with
Ir
Complexes
328
13.4
Alkane Dehydrogenation Catalyzed by
Ir
Pincer
Complexes
333
ПАЛ
Ir-PCP
Pincer
Compounds
333
13.4.2
Ir-POCOP
Pincer
Compounds
336
Contents
XI
13.5 Final
Remarks
342
Acknowledgments
342
References
342
Ί4
Transformations of (Organojsilicon Compounds Catalyzed by Indium
Complexes
345
Bogdan Marciniec
and
Ireneusz Kownacki
14.1
Introduction
345
14.2
Hydrosilylation and Dehydrogenative Silylation of Carbon-Carbon
Multiple Bonds
346
14.2.1
Hydrosilylation and Dehydrogenative Silylation of Alkenes
346
14.2.2
Application of Hydrosilylation in Polymer Chemistry
348
14.2.3
Hydrosilylation and Dehydrogenative Silylation of Alkynes
349
14.3
Asymmetric Hydrosilylation of Ketones and Imines
352
14.4
Transformation of Organosilicon Compounds in the Presence of
Carbon Monoxide
356
14.4.1
Hydroformylation of Vinylsilanes
356
14.4.2
Silylcarbonylation of Alkenes and Alkynes
357
14.5
Silylation of Aromatic Carbon-Hydrogen Bonds
359
14.6
Silylation of Alkenes with Vinylsilanes
360
14.7
Alcoholysis and
Oxygénation
of Hydrosilanes
362
14.8
Isomerization of Silyl Olefins
362
14.9
Addition of silylacetglenes sC—
H
Bonds into Imines
362
14.10
Conclusions
364
References
365
15
Catalytic Properties of Soluble
Iridium Nanoparticles
369
Jackson D.
Scholten
andjaïrton Dupont
15.1
Introduction
369
15.2
Synthesis of Soluble Iridium Nanoparticles
369
15.2.1
Polyoxoanions
369
15.2.2
Surfactants
370
15.2.3
Imidazolium Ionic Liquids
372
15.3
Kinetic Studies of Iridium Nanoparticle Formation:
The Autocatalytic Mechanism
377
15.4
Catalytic Applications of Soluble Iridium Nanoparticles
380
15.5
Conclusions
387
References
388
Index
391 |
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| id | DE-604.BV035188801 |
| illustrated | Illustrated |
| index_date | 2024-07-02T23:00:56Z |
| indexdate | 2024-07-20T09:57:27Z |
| institution | BVB |
| isbn | 9783527319961 |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-016995446 |
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| physical | XVII, 396 S. Ill., graph. Darst. |
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| spelling | Iridium Complexes in Organic Synthesis Hrsg. Luis A. Oro ; Hrsg. Carmen Claver 1. Aufl. Weinheim, Bergstr WILEY-VCH 2009 XVII, 396 S. Ill., graph. Darst. txt rdacontent n rdamedia nc rdacarrier "Ranging from mechanistic studies to industrial applications, this handbook is the first to comprehensively explore the topic of iridium in organic synthesis. The important advances in iridium mediated reactions namely hydrogenation, hydroamination, hydroboration, C-C bond formation, carbonylation and cycloaddition are discussed. The book presents the most widely exploited iridium catalysed reactions, such as asymmetric reductions, together with the recent advances including the use of soluble metal nanoparticles as catalysts. In general terms, this book covers the application of iridium catalysts in organic synthesis from the more basic reactions to highlighted topics, including the use of specific ligands in the most important class of transition metal catalysed reactions."--BOOK JACKET. Asymmetric synthesis Iridium catalysts Organic compounds Synthesis Organische Synthese (DE-588)4075695-6 gnd rswk-swf Iridiumkomplexe (DE-588)4223130-9 gnd rswk-swf Iridiumkomplexe (DE-588)4223130-9 s Organische Synthese (DE-588)4075695-6 s DE-604 Oro, Luis A. edt Claver, Carmen edt text/html http://deposit.dnb.de/cgi-bin/dokserv?id=3113105&prov=M&dok_var=1&dok_ext=htm Inhaltstext Digitalisierung UB Bayreuth application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=016995446&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Iridium Complexes in Organic Synthesis Asymmetric synthesis Iridium catalysts Organic compounds Synthesis Organische Synthese (DE-588)4075695-6 gnd Iridiumkomplexe (DE-588)4223130-9 gnd |
| subject_GND | (DE-588)4075695-6 (DE-588)4223130-9 |
| title | Iridium Complexes in Organic Synthesis |
| title_auth | Iridium Complexes in Organic Synthesis |
| title_exact_search | Iridium Complexes in Organic Synthesis |
| title_exact_search_txtP | Iridium Complexes in Organic Synthesis |
| title_full | Iridium Complexes in Organic Synthesis Hrsg. Luis A. Oro ; Hrsg. Carmen Claver |
| title_fullStr | Iridium Complexes in Organic Synthesis Hrsg. Luis A. Oro ; Hrsg. Carmen Claver |
| title_full_unstemmed | Iridium Complexes in Organic Synthesis Hrsg. Luis A. Oro ; Hrsg. Carmen Claver |
| title_short | Iridium Complexes in Organic Synthesis |
| title_sort | iridium complexes in organic synthesis |
| topic | Asymmetric synthesis Iridium catalysts Organic compounds Synthesis Organische Synthese (DE-588)4075695-6 gnd Iridiumkomplexe (DE-588)4223130-9 gnd |
| topic_facet | Asymmetric synthesis Iridium catalysts Organic compounds Synthesis Organische Synthese Iridiumkomplexe |
| url | http://deposit.dnb.de/cgi-bin/dokserv?id=3113105&prov=M&dok_var=1&dok_ext=htm http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=016995446&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT oroluisa iridiumcomplexesinorganicsynthesis AT clavercarmen iridiumcomplexesinorganicsynthesis |