Transition metal-catalyzed carbene transformations:
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| Sprache: | English |
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[2022]
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| Beschreibung: | xiv, 427 Seiten Illustrationen, Diagramme 24.4 cm x 17 cm |
| ISBN: | 9783527347995 3527347992 |
Internformat
MARC
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| 015 | |a 21,N32 |2 dnb | ||
| 016 | 7 | |a 1238379613 |2 DE-101 | |
| 020 | |a 9783527347995 |c hbk. |9 978-3-527-34799-5 | ||
| 020 | |a 3527347992 |9 3-527-34799-2 | ||
| 035 | |a (OCoLC)1306332646 | ||
| 035 | |a (DE-599)DNB1238379613 | ||
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| 084 | |a VK 5550 |0 (DE-625)147403:253 |2 rvk | ||
| 245 | 1 | 0 | |a Transition metal-catalyzed carbene transformations |c edited by Jianbo Wang, Chi-Ming Che and Michael P. Doyle |
| 264 | 1 | |a Weinheim |b Wiley-VCH |c [2022] | |
| 264 | 4 | |c © 2022 | |
| 300 | |a xiv, 427 Seiten |b Illustrationen, Diagramme |c 24.4 cm x 17 cm | ||
| 336 | |b txt |2 rdacontent | ||
| 337 | |b n |2 rdamedia | ||
| 338 | |b nc |2 rdacarrier | ||
| 650 | 0 | 7 | |a Katalyse |0 (DE-588)4029921-1 |2 gnd |9 rswk-swf |
| 650 | 0 | 7 | |a Carbene |0 (DE-588)4147281-0 |2 gnd |9 rswk-swf |
| 650 | 0 | 7 | |a Übergangsmetallkomplexe |0 (DE-588)4131837-7 |2 gnd |9 rswk-swf |
| 653 | |a Catalysis | ||
| 653 | |a Chemie | ||
| 653 | |a Chemistry | ||
| 653 | |a Katalyse | ||
| 653 | |a Organic Chemistry | ||
| 653 | |a Organische Chemie | ||
| 653 | |a Polymer Science & Technology | ||
| 653 | |a Polymer Synthesis | ||
| 653 | |a Polymersynthese | ||
| 653 | |a Polymerwissenschaft u. -technologie | ||
| 653 | |a CH40: Katalyse | ||
| 653 | |a CH80: Organische Chemie | ||
| 653 | |a PY30: Polymersynthese | ||
| 655 | 7 | |0 (DE-588)4143413-4 |a Aufsatzsammlung |2 gnd-content | |
| 689 | 0 | 0 | |a Carbene |0 (DE-588)4147281-0 |D s |
| 689 | 0 | 1 | |a Katalyse |0 (DE-588)4029921-1 |D s |
| 689 | 0 | 2 | |a Übergangsmetallkomplexe |0 (DE-588)4131837-7 |D s |
| 689 | 0 | |5 DE-604 | |
| 700 | 1 | |a Wang, Jianbo |d 1962- |0 (DE-588)102580337X |4 edt | |
| 700 | 1 | |a Che, Chi-Ming |4 edt | |
| 700 | 1 | |a Doyle, Michael P. |d 1942- |0 (DE-588)172047722 |4 edt | |
| 710 | 2 | |a Wiley-VCH |0 (DE-588)16179388-5 |4 pbl | |
| 776 | 0 | 8 | |i Erscheint auch als |n Online-Ausgabe, PDF |z 978-3-527-82916-3 |
| 776 | 0 | 8 | |i Erscheint auch als |n Online-Ausgabe, ePub |z 978-3-527-82915-6 |
| 776 | 0 | 8 | |i Erscheint auch als |n Online-Ausgabe, oBook |z 978-3-527-82917-0 |
| 856 | 4 | 2 | |m X:MVB |u http://www.wiley-vch.de/publish/dt/books/ISBN978-3-527-34799-5/ |3 Beschreibung für Leser |
| 856 | 4 | 2 | |m DNB Datenaustausch |q application/pdf |u http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=033045023&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |3 Inhaltsverzeichnis |
| 999 | |a oai:aleph.bib-bvb.de:BVB01-033045023 | ||
Datensatz im Suchindex
| _version_ | 1804183130750320640 |
|---|---|
| adam_text | CONTENTS
PREFACE
XIII
1
ALKANE
FUNCTIONALIZATION
BY
METAL-CATALYZED
CARBENE
INSERTION
FROM
DIAZO
REAGENTS
1
MARIA
ALVAREZ,
ANA
CABALLERO,
AND
PEDRO
J.
PEREZ
1.1
INTRODUCTION
1
1.2
CHEMO
AND
REGIOSELECTIVITY
3
1.2.1
DEFINITIONS
3
1.2.2
CATALYSTS
5
1.2.3
CHEMOSELECTIVITY
6
1.2.4
REGIOSELECTIVITY
8
1.3
ENANTIOSELECTIVITY
9
1.4
METHANE
AND
GASEOUS
ALKANES
AS
SUBSTRATES
14
1.5
ALKANE
NUCLEOPHILICITY
SCALE
18
1.6
CONCLUSIONS
AND
OUTLOOK
22
ACKNOWLEDGMENTS
22
REFERENCES
22
2
CATALYTIC
RADICAL
APPROACH
FOR
SELECTIVE
CARBENE
TRANSFERS
VIA
COBALT(LL)-BASED
METALLORADICAL
CATALYSIS
25
XIAOXU
WANG
AND
X.
PETER
ZHANG
2.1
INTRODUCTION
25
2.2
INTERMOLECULAR
RADICAL
CYCLOPROPANATION
OF
ALKENES
26
2.2.1
CYCLOPROPANATION
WITH
ACCEPTOR-SUBSTITUTED
DIAZO
COMPOUNDS
27
2.2.2
CYCLOPROPANATION
WITH
ACCEPTOR/ACCEPTOR-SUBSTITUTED
DIAZO
COMPOUNDS
32
2.2.3
CYCLOPROPANATION
WITH
DONOR-SUBSTITUTED
DIAZO
COMPOUNDS
37
2.3
INTRAMOLECULAR
RADICAL
CYCLOPROPANATION
OF
ALKENES
39
2.4
INTERMOLECULAR
RADICAL
CYCLOPROPENATION
OF
ALKYNES
43
2.5
INTRAMOLECULAR
RADICAL
ALKYLATION
OF
C(SP
3
)-H
BONDS
44
2.5.1
INTRAMOLECULAR
C-H
ALKYLATION
WITH
ACCEPTOR/ACCEPTOR-SUBSTITUTED
DIAZO
COMPOUNDS
45
VI
CONTENTS
2.5.2
INTRAMOLECULAR
C-H
ALKYLATION
WITH
DONOR-SUBSTITUTED
DIAZO
COMPOUNDS
46
2.6
2.7
OTHER
CATALYTIC
RADICAL
PROCESSES
FOR
CARBENE
TRANSFERS
54
SUMMARY
AND
OUTLOOK
59
ACKNOWLEDGMENT
60
REFERENCES
60
3
CATALYTIC
ENANTIOSELECTIVE
CARBENE
INSERTIONS
INTO
HETEROATOM-HYDROGEN
BONDS
67
MING-YAO
HUANG,
SHOU-FEI
ZHU,
AND
QI-LIN
ZHOU
3.1
3.2
3.2.1
3.2.1.1
3.2.1.2
3.2.1.3
3.2.1.4
3.2.1.5
3.2.1.6
3.2.1.7
3.3
3.3.1
3.3.1.1
3.3.1.2
3.3.1.3
3.3.1.4
3.3.1.5
3.3.1.6
3.4
3.4.1
3.4.2
3.4.3
3.5
3.6
3.6.1
3.6.2
3.6.3
3.6.4
3.7
3.7.1
3.7.2
3.7.3
3.8
INTRODUCTION
67
N
-
H
BOND
INSERTION
REACTIONS
67
CHIRAL
METAL CATALYSTS
68
CHIRAL
CU
CATALYSTS
68
CHIRAL
PD
CATALYSTS
70
OTHER
CHIRAL
METAL CATALYSTS
70
ENZYMES
72
CHIRAL
PROTON-TRANSFER
SHUTTLE
CATALYSTS
72
CHIRAL
PHOSPHORIC
ACIDS
AS
CPTS
CATALYSTS
72
CHIRAL
AMINO
THIOUREAS
AS
CPTS
CATALYSTS
73
0
-H
BOND
INSERTION
REACTIONS
74
CHIRAL
METAL
CATALYSTS
74
CHIRAL
CU CATALYSTS
74
CHIRAL
FE
CATALYSTS
76
CHIRAL
PD
CATALYSTS
77
CHIRAL
AU
CATALYSTS
78
CHIRAL
BASES
AS
CPTS
CATALYSTS
78
CHIRAL
PHOSPHORIC
ACIDS
AS
CPTS
CATALYSTS
79
S
-
H
BOND
INSERTION
REACTIONS
80
CHIRAL
METAL
CATALYSTS
80
CPTS
CATALYSTS
81
ENZYMES
81
F
-
H
BOND
INSERTION
REACTIONS
82
SI
-
H
BOND
INSERTION
REACTIONS
83
CHIRAL
RH
CATALYSTS
83
CHIRAL
CU
CATALYSTS
85
OTHER
CHIRAL
METAL
CATALYSTS
86
ENZYMES
87
B
-H
BOND
INSERTION
REACTIONS
88
CHIRAL
CU
CATALYSTS
88
CHIRAL
RHODIUM
CATALYSTS
89
ENZYMES
89
SUMMARY
AND
OUTLOOK
90
REFERENCES
91
CONTENTS
VII
4
ENGINEERING
ENZYMES
FOR
NEW-TO-NATURE
CARBENE
CHEMISTRY
95
SOUMITRA
V.
ATHAVALE,
KAI
CHEN,
AND
FRANCES
H.
ARNOLD
4.1
INTRODUCTION:
BIOLOGY
INSPIRES
CHEMISTRY
INSPIRES
BIOLOGY
95
4.2
P411-CATALYZED
CYCLOPROPANATION
99
4.3
THE
WORKFLOW
OF
DIRECTED
EVOLUTION
101
4.4
EXPANDING
CYCLOPROPANATION
WITH
DIVERSE
HEMEPROTEIN
CARBENE
TRANSFERASES
102
4.5
C-H
FUNCTIONALIZATION
WITH
CARBENE
TRANSFERASES
109
4.6
BIOCATALYTIC
CARBENE
X-H
INSERTION
113
4.7
CARBENE
TRANSFER
REACTIONS
WITH
ARTIFICIAL
METALLOPROTEINS
118
4.8
STRUCTURAL
STUDIES
OF
CARBENE
INTERMEDIATES
IN
HEME
PROTEINS
125
4.9
SUMMARY
128
ACKNOWLEDGMENTS
129
REFERENCES
129
5
METAL
CARBENE
CYCLOADDITION
REACTIONS
139
KOSTIANTYN
0.
MARICHEV,
HAIFENG
ZHENG,
AND
MICHAEL
P.
DOYLE
5.1
INTRODUCTION
139
5.2
[3+L]-CYCLOADDITION
142
5.3
[3+2]-CYCLOADDITION
145
5.3.1
[3+2]-CYCLOADDITION
WITH
IMINES
AND
INDOLES
145
5.3.2
[3+2]-CYCLOADDITION
WITH
POLARIZED
ALKENES
149
5.3.3
[3+2]-CYCLOADDITION
WITH
NITRONES
150
5.3.4
DIVERGENT
BEHAVIOR
OF
CATALYSTS
151
5.4
[3+3]-CYCLOADDITION
OF
ENOLDIAZO
COMPOUNDS
152
5.4.1
[3+3]-CYCLOADDITION
WITH
NITRONES
152
5.4.2
[3+3]-CYCLOADDITION
WITH
PYRIDINIUM
YLIDES
AND
HYDRAZONES
155
5.4.3
DIASTEREOSELECTIVE
[3+3]-CYCLOADDITION
WITH
ACHIRAL
CATALYSTS
157
5.4.4
[3+3]-CYCLOADDITION
WITH
DIAZIRIDINES
158
5.4.5
[3+3]-CYCLOADDITION
WITH
DONOR-ACCEPTOR
CYCLOPROPANES
AND
OXIRANES
159
5.5
[3+4]-CYCLOADDITION
160
5.6
[3+5]-CYCLOADDITION
161
5.7
SUMMARY
162
REFERENCES
163
6
METAL-CATALYZED
DECARBENATIONS
BY
RETRO-CYCLOPROPANATION
169
MAURO
MATO
AND
ANTONIO
M.
ECHAVARREN
6.1
INTRODUCTION
169
6.2
REACTIVITY
AND
GENERATION
OF
METAL
CARBENES
169
6.2.1
DECOMPOSITION
OF
DIAZO
COMPOUNDS
170
6.2.2
ALTERNATIVE
METHODS
FOR
THE
GENERATION
OF
METAL
CARBENES
170
VIII
CONTENTS
6.2.3
DECARBENATION
REACTIONS:
GENERAL
PROCESS
AND
DEFINITION
170
6.3
RETRO-CYCLOPROPANATION
REACTIONS:
A
HISTORICAL
WALKTHROUGH
171
6.3.1
EARLY
OBSERVATIONS
171
6.3.2
DECARBENATION
REACTIONS
FROM
GAS
PHASE
TO
SOLUTION
173
6.3.3
THE
DISCOVERY
OF
THE
GOLD(I)-CATALYZED
RETRO-BUCHNER
REACTION
173
6.4
METAL-CATALYZED
AROMATIVE-DECARBENATION
REACTIONS:
A
MECHANISTIC
ANALYSIS
175
6.4.1
BASIC
MECHANISTIC
PICTURE
175
6.4.2
ALTERNATIVE
GENERATION
OF
THE
SAME
CARBENES
FROM
CARBENOIDS
175
6.4.3
THEORETICAL
STUDIES
ON
THE
MECHANISM
OF
THE
RETRO-BUCHNER
REACTION
177
6.4.4
SECOND-GENERATION
CYCLOHEPTATRIENES:
LOW
TEMPERATURE
AND
OTHER
METALS
179
6.4.5
MECHANISM
OF
THE
RH(II)-CATALYZED
AROMATIVE
DECARBENATION
181
6.5
SYNTHETIC
METHODOLOGIES
AND
APPLICATIONS
181
6.5.1
CYCLOPROPANATION
REACTIONS
181
6.5.1.1
ARYL
CYCLOPROPANATIONS
183
6.5.1.2
ALKENYL
CYCLOPROPANATIONS
184
6.5.1.3
REACTIONS
WITH
FURANS
185
6.5.2
HIGHER
FORMAL
CYCLOADDITIONS
186
6.5.2.1
(4+1)
CYCLOADDITIONS
187
6.5.2.2
(3+2)
CYCLOADDITIONS
187
6.5.2.3
(4+3)
CYCLOADDITIONS
189
6.5.3
INTRAMOLECULAR
FRIEDEL-CRAFTS
REACTIVITY
190
6.5.4
INSERTION
REACTIONS
190
6.5.4.1
C-H
INSERTION
190
6.5.4.2
SI-H
INSERTION
192
6.5.5
OXIDATION
REACTIONS
192
6.5.6
ALTERNATIVE
PRECURSORS
193
6.5.7
DECARBENATIONS
BASED
ON
THE
RELEASE
OF
ALKENES
193
6.6
GENERAL
OUTLOOK
AND
CONCLUDING
REMARKS
195
REFERENCES
196
7
GOLD-CATALYZED
OXIDATION
OF
ALKYNES
BY
N-OXIDES
OR
SULFOXIDES
199
KAYLAA
GUTMAN,
TIANYOU
LI,
AND
LIMING
ZHANG
7.1
INTRODUCTION:
GOLD-ACTIVATED
ALKYNES
ATTACKED
BY
NUCLEOPHILIC
OXIDANTS
199
7.2
SULFOXIDES
AS
NUCLEOPHILIC
OXIDANTS
201
7.3
N-OXIDES
AS
NUCLEOPHILIC
OXIDANTS
202
7.3.1
REACTIONS
OF
CARBENE/CARBENOID
INTERMEDIATES
WITH
OXYGEN-BASED
NUCLEOPHILES
205
7.3.2
REACTIONS
OF
CARBENE/CARBENOID
INTERMEDIATES
WITH
NITROGEN-BASED
NUCLEOPHILES
212
CONTENTS
IX
7.3.3
REACTIONS
OF
CARBENE/CARBENOID
INTERMEDIATES
WITH
OTHER
HETERONUCLEOPHILES
214
7.3.4
FRIEDEL-CRAFTS
REACTIONS
OF
CARBENE/CARBENOID
INTERMEDIATES
WITH
ARENES
215
7.3.5
REACTIONS
OF
CARBENE/CARBENOID
INTERMEDIATES
WITH
ALKENES
218
7.3.6
REACTIONS
OF
CARBENE/CARBENOID
INTERMEDIATES
WITH
C
-
C
TRIPLE
BONDS
224
7.3.7
1,2-C-C
AND
1,2-C-H
INSERTIONS
OF
CARBENE/CARBENOID
INTERMEDIATES
226
7.3.8
REMOTE
C(SP
3
)-H
FUNCTIONALIZATIONS
BY
CARBENE/CARBENOID
INTERMEDIATES
231
7.4
CONCLUSION
238
REFERENCES
238
8
TRANSITION-METAL-CATALYZED
CARBENE
TRANSFORMATIONS
FOR
POLYMER
SYNTHESES
243
EIJI
LHARA
AND
HIROAKI
SHIMOMOTO
8.1
INTRODUCTION
243
8.2
TRANSITION-METAL-CATALYZED
CL
POLYMERIZATION
OF
DIAZOACETATES
243
8.2.1
PDCL
2
-INITIATED
POLYMERIZATION
244
8.2.2
(NHC)PD(NQ)/BORATE-INITIATED
POLYMERIZATION
245
8.2.3
%-ALLYLPDCL-BASED
SYSTEM-INITIATED
POLYMERIZATION
246
8.2.4
(NQ)
2
PD/BORATE-
AND
(COD)PDCL(CL-NQ)/BORATE-INITIATED
POLYMERIZATION
251
8.2.5
PREPARATION
OF
POLYMERS
WITH
DENSELY
PACKED
FUNCTIONAL
GROUPS
AROUND
POLYMER
MAIN
CHAIN
254
8.2.5.1
HYDROXY
GROUP-CONTAINING
POLYMERS
254
8.2.5.2
OLIGO(OXYETHYLENE)-CONTAINING
POLYMERS
256
8.2.5.3
PYRENE-CONTAINING
POLYMERS
257
8.2.5.4
FLUOROALKYL
AND
FLUOROARYL
GROUP-CONTAINING
POLYMERS
258
8.3
POLYCONDENSATION
OF
BIS(DIAZOCARBONYL)
COMPOUNDS
259
8.3.1
THREE-COMPONENT
POLYCONDENSATION
OF
BIS(DIAZOCARBONYL)
COMPOUND,
DIOL,
AND
THF
259
8.3.2
THREE-COMPONENT
POLYCONDENSATION
OF
BIS(DIAZOCARBONYL)
COMPOUND,
DICARBOXYLIC
ACID,
AND
THF
262
8.3.3
THREE-COMPONENT
POLYCONDENSATION
OF
BIS(DIAZOCARBONYL)
COMPOUND,
ENOL-FORM
OF
1,3-DIKETONE,
AND
THF
263
8.3.4
TWO-COMPONENT
POLYCONDENSATION
OF
BIS(DIAZOCARBONYL)
COMPOUND
WITH
AROMATIC
DIAMINE
264
8.3.5
SINGLE-COMPONENT
POLYCONDENSATION
OF
BIS(DIAZOCARBONYL)
COMPOUND
TO
AFFORD
UNSATURATED
POLYESTERS
264
8.3.6
SINGLE-COMPONENT
POLYCONDENSATION
OF
BIS(DIAZOCARBONYL)
COMPOUND
TO
AFFORD
POLY(ARYLENE
VINYLENE)S
(PAV)
265
CONTENTS
8.4
CONCLUDING
REMARKS
266
REFERENCES
266
9
METAL-CATALYZED
QUINOID
CARBENE
(QC)
TRANSFER
REACTIONS
269
HAI-XU
WANG,
VANESSA
K.-Y.
LO,
AND
CHI-MING
CHE
9.1
INTRODUCTION
269
9.2
METAI-QUINOID
CARBENE
(QC)
COMPLEXES
AND
STOICHIOMETRIC
REACTIVITY
269
9.3
METAL-CATALYZED
QC
TRANSFER
REACTIONS
273
9.3.1
CYCLOPROPANATION
REACTIONS
273
9.3.2
C(SP
2
)-H
INSERTION
REACTIONS
275
9.3.3
C(SP
3
)-H
INSERTION
REACTIONS
284
9.3.4
NUCLEOPHILIC
ADDITION
AND
MISCELLANEOUS
REACTIONS
286
9.4
CONCLUSION
293
ACKNOWLEDGMENT
295
REFERENCES
295
10
ASYMMETRIC
REARRANGEMENT
AND
INSERTION
REACTIONS
WITH
METAL-CARBENOIDS
PROMOTED
BY
CHIRAL
N,N -DIOXIDE
OR
GUANIDINE-BASED
CATALYSTS
299
XIAOBIN
LIN,
XIAOHUA
LIU,
AND
XIAOMING
FENG
10.1
INTRODUCTION
299
10.2
THE
INTRODUCTION
OF
CHIRAL
NJV -DIOXIDE/METAL
COMPLEXES
AND
GUANIDINE
CATALYSTS
299
10.3
CHIRAL
N,N -DIOXIDE/METAL
COMPLEXES-CATALYZED
REARRANGEMENT
REACTIONS
302
10.4
CHIRAL
GUANIDINE-BASED
CATALYST-MEDIATED
ASYMMETRIC
CARBENE
INSERTION
REACTIONS
315
10.5
CONCLUSION
AND
OUTLOOK
323
REFERENCES
323
11
MULTI-COMPONENT
REACTION
VIA
GEM-DIFUNCTIONALIZATION
OF
METAL
CARBENE
325
MENGCHU
ZHANG,
XINFANG
XU,
AND
WENHAO
HU
11.1
INTRODUCTION
325
11.2
MANNICH-TYPE
INTERCEPTION
327
11.2.1
INTERCEPTION
OF
AMMONIUM
YLIDE
327
11.2.2
INTERCEPTION
OF
OXONIUM
YLIDE
328
11.2.3
INTERCEPTION
OF
ZWITTERIONIC
INTERMEDIATE
339
11.3
ALDOL-TYPE
INTERCEPTION
340
11.3.1
INTERCEPTION
OF
AMMONIUM
YLIDE
340
11.3.2
INTERCEPTION
OF
OXONIUM
YLIDE
342
CONTENTS
XI
11.3.3
INTERCEPTION
OF
ZWITTERIONIC
INTERMEDIATE
343
11.4
MICHAEL-TYPE
INTERCEPTION
345
11.4.1
INTERCEPTION
OF
AMMONIUM
YLIDE
345
11.4.2
INTERCEPTION
OF
OXONIUM
YLIDE
346
11.4.3
INTERCEPTION
OF
ZWITTERIONIC
INTERMEDIATE
348
11.5
MISCELLANEOUS
TRANSFORMATIONS
349
11.5.1
INTERCEPTION
OTHER
TYPES
OF
ACTIVE
INTERMEDIATES
349
11.5.2
INTERCEPTION
OF
ACTIVE
INTERMEDIATES
WITH
OTHER
ELECTROPHILES
353
11.5.3
APPLICATIONS
IN
CASCADE
REACTIONS
355
11.6
SYNTHETIC
APPLICATIONS
358
11.6.1
SYNTHESIS
AND
M
ODIFICATION
OF
NATURAL
PRODUCTS
358
11.6.2
SYNTHESIS
OF
BIOACTIVE
MOLECULES
362
11.7
CONCLUSION
364
REFERENCES
365
12
TRANSITION-METAL-CATALYZED
CROSS-COUPLING
WITH
CARBENE
PRECURSORS
371
KANG
WANG
AND
JIANBO
WANG
12.1
INTRODUCTION
371
12.2
PALLADIUM-CATALYZED
CARBENE
CROSS-COUPLING REACTIONS
372
12.2.1
DIAZO
COMPOUNDS
AS
CARBENE
PRECURSORS
372
12.2.1.1
REACTIONS
WITH
ELECTROPHILES
372
12.2.1.2
REACTIONS
WITH
NUCLEOPHILES
373
12.2.1.3
PALLADIUM-CATALYZED
CASCADE
CROSS-COUPLING
REACTIONS
374
12.2.2
N-TOSYLHYDRAZONES
AS
CARBENE
PRECURSORS
377
12.2.2.1
REACTIONS
WITH
ELECTROPHILES
377
12.2.2.2
REACTIONS
WITH
NUCLEOPHILES
379
12.2.2.3
PALLADIUM-CATALYZED
CASCADE
CROSS-COUPLING
REACTIONS
380
12.2.3
NON-DIAZO
COMPOUNDS
AS
CARBENE
PRECURSORS
382
12.3
COPPER-CATALYZED
CARBENE
CROSS-COUPLING REACTIONS
385
12.3.1
REACTIONS
WITH
TERMINAL
ALKYNES
385
12.3.1.1
MULTI-SUBSTITUTED
ALLENES
AS
THE
COUPLING
PRODUCTS
385
12.3.1.2
INTERNAL
ALKYNES
AS
THE
COUPLING
PRODUCTS
386
12.3.2
REACTIONS
WITH
OTHER
COUPLING
PARTNERS
387
12.4
RHODIUM-CATALYZED
CARBENE
CROSS-COUPLING REACTIONS
388
12.4.1
GENERATING
ORGANORHODIUM
SPECIES
THROUGH
TRANSMETALATION
388
12.4.2
GENERATING
ORGANORHODIUM
SPECIES
THROUGH
C
-
C
BOND
CLEAVAGE
389
12.5
TRANSITION-METAL-CATALYZED
C
-
H
BOND
FUNCTIONALIZATIONS
WITH
CARBENE
PRECURSORS
391
12.5.1
NON-DIRECTING-GROUP-ASSISTED
C
-H
FUNCTIONALIZATIONS
391
12.5.2
DIRECTING-GROUP-ASSISTED
C
-
H
BOND
FUNCTIONALIZATIONS
393
12.5.2.1
GENERATING
ACYCLIC
PRODUCTS
THROUGH
C
-
H
BOND
ACTIVATION
393
12.5.2.2
GENERATING
CYCLIC
PRODUCTS
THROUGH
C
-H
BOND
ACTIVATION
394
XII
|
CONTENTS
12.6
CONCLUSION
REMARKS
396
ACKNOWLEDGMENT
397
REFERENCES
397
INDEX
401
|
| adam_txt |
CONTENTS
PREFACE
XIII
1
ALKANE
FUNCTIONALIZATION
BY
METAL-CATALYZED
CARBENE
INSERTION
FROM
DIAZO
REAGENTS
1
MARIA
ALVAREZ,
ANA
CABALLERO,
AND
PEDRO
J.
PEREZ
1.1
INTRODUCTION
1
1.2
CHEMO
AND
REGIOSELECTIVITY
3
1.2.1
DEFINITIONS
3
1.2.2
CATALYSTS
5
1.2.3
CHEMOSELECTIVITY
6
1.2.4
REGIOSELECTIVITY
8
1.3
ENANTIOSELECTIVITY
9
1.4
METHANE
AND
GASEOUS
ALKANES
AS
SUBSTRATES
14
1.5
ALKANE
NUCLEOPHILICITY
SCALE
18
1.6
CONCLUSIONS
AND
OUTLOOK
22
ACKNOWLEDGMENTS
22
REFERENCES
22
2
CATALYTIC
RADICAL
APPROACH
FOR
SELECTIVE
CARBENE
TRANSFERS
VIA
COBALT(LL)-BASED
METALLORADICAL
CATALYSIS
25
XIAOXU
WANG
AND
X.
PETER
ZHANG
2.1
INTRODUCTION
25
2.2
INTERMOLECULAR
RADICAL
CYCLOPROPANATION
OF
ALKENES
26
2.2.1
CYCLOPROPANATION
WITH
ACCEPTOR-SUBSTITUTED
DIAZO
COMPOUNDS
27
2.2.2
CYCLOPROPANATION
WITH
ACCEPTOR/ACCEPTOR-SUBSTITUTED
DIAZO
COMPOUNDS
32
2.2.3
CYCLOPROPANATION
WITH
DONOR-SUBSTITUTED
DIAZO
COMPOUNDS
37
2.3
INTRAMOLECULAR
RADICAL
CYCLOPROPANATION
OF
ALKENES
39
2.4
INTERMOLECULAR
RADICAL
CYCLOPROPENATION
OF
ALKYNES
43
2.5
INTRAMOLECULAR
RADICAL
ALKYLATION
OF
C(SP
3
)-H
BONDS
44
2.5.1
INTRAMOLECULAR
C-H
ALKYLATION
WITH
ACCEPTOR/ACCEPTOR-SUBSTITUTED
DIAZO
COMPOUNDS
45
VI
CONTENTS
2.5.2
INTRAMOLECULAR
C-H
ALKYLATION
WITH
DONOR-SUBSTITUTED
DIAZO
COMPOUNDS
46
2.6
2.7
OTHER
CATALYTIC
RADICAL
PROCESSES
FOR
CARBENE
TRANSFERS
54
SUMMARY
AND
OUTLOOK
59
ACKNOWLEDGMENT
60
REFERENCES
60
3
CATALYTIC
ENANTIOSELECTIVE
CARBENE
INSERTIONS
INTO
HETEROATOM-HYDROGEN
BONDS
67
MING-YAO
HUANG,
SHOU-FEI
ZHU,
AND
QI-LIN
ZHOU
3.1
3.2
3.2.1
3.2.1.1
3.2.1.2
3.2.1.3
3.2.1.4
3.2.1.5
3.2.1.6
3.2.1.7
3.3
3.3.1
3.3.1.1
3.3.1.2
3.3.1.3
3.3.1.4
3.3.1.5
3.3.1.6
3.4
3.4.1
3.4.2
3.4.3
3.5
3.6
3.6.1
3.6.2
3.6.3
3.6.4
3.7
3.7.1
3.7.2
3.7.3
3.8
INTRODUCTION
67
N
-
H
BOND
INSERTION
REACTIONS
67
CHIRAL
METAL CATALYSTS
68
CHIRAL
CU
CATALYSTS
68
CHIRAL
PD
CATALYSTS
70
OTHER
CHIRAL
METAL CATALYSTS
70
ENZYMES
72
CHIRAL
PROTON-TRANSFER
SHUTTLE
CATALYSTS
72
CHIRAL
PHOSPHORIC
ACIDS
AS
CPTS
CATALYSTS
72
CHIRAL
AMINO
THIOUREAS
AS
CPTS
CATALYSTS
73
0
-H
BOND
INSERTION
REACTIONS
74
CHIRAL
METAL
CATALYSTS
74
CHIRAL
CU CATALYSTS
74
CHIRAL
FE
CATALYSTS
76
CHIRAL
PD
CATALYSTS
77
CHIRAL
AU
CATALYSTS
78
CHIRAL
BASES
AS
CPTS
CATALYSTS
78
CHIRAL
PHOSPHORIC
ACIDS
AS
CPTS
CATALYSTS
79
S
-
H
BOND
INSERTION
REACTIONS
80
CHIRAL
METAL
CATALYSTS
80
CPTS
CATALYSTS
81
ENZYMES
81
F
-
H
BOND
INSERTION
REACTIONS
82
SI
-
H
BOND
INSERTION
REACTIONS
83
CHIRAL
RH
CATALYSTS
83
CHIRAL
CU
CATALYSTS
85
OTHER
CHIRAL
METAL
CATALYSTS
86
ENZYMES
87
B
-H
BOND
INSERTION
REACTIONS
88
CHIRAL
CU
CATALYSTS
88
CHIRAL
RHODIUM
CATALYSTS
89
ENZYMES
89
SUMMARY
AND
OUTLOOK
90
REFERENCES
91
CONTENTS
VII
4
ENGINEERING
ENZYMES
FOR
NEW-TO-NATURE
CARBENE
CHEMISTRY
95
SOUMITRA
V.
ATHAVALE,
KAI
CHEN,
AND
FRANCES
H.
ARNOLD
4.1
INTRODUCTION:
BIOLOGY
INSPIRES
CHEMISTRY
INSPIRES
BIOLOGY
95
4.2
P411-CATALYZED
CYCLOPROPANATION
99
4.3
THE
WORKFLOW
OF
DIRECTED
EVOLUTION
101
4.4
EXPANDING
CYCLOPROPANATION
WITH
DIVERSE
HEMEPROTEIN
CARBENE
TRANSFERASES
102
4.5
C-H
FUNCTIONALIZATION
WITH
CARBENE
TRANSFERASES
109
4.6
BIOCATALYTIC
CARBENE
X-H
INSERTION
113
4.7
CARBENE
TRANSFER
REACTIONS
WITH
ARTIFICIAL
METALLOPROTEINS
118
4.8
STRUCTURAL
STUDIES
OF
CARBENE
INTERMEDIATES
IN
HEME
PROTEINS
125
4.9
SUMMARY
128
ACKNOWLEDGMENTS
129
REFERENCES
129
5
METAL
CARBENE
CYCLOADDITION
REACTIONS
139
KOSTIANTYN
0.
MARICHEV,
HAIFENG
ZHENG,
AND
MICHAEL
P.
DOYLE
5.1
INTRODUCTION
139
5.2
[3+L]-CYCLOADDITION
142
5.3
[3+2]-CYCLOADDITION
145
5.3.1
[3+2]-CYCLOADDITION
WITH
IMINES
AND
INDOLES
145
5.3.2
[3+2]-CYCLOADDITION
WITH
POLARIZED
ALKENES
149
5.3.3
[3+2]-CYCLOADDITION
WITH
NITRONES
150
5.3.4
DIVERGENT
BEHAVIOR
OF
CATALYSTS
151
5.4
[3+3]-CYCLOADDITION
OF
ENOLDIAZO
COMPOUNDS
152
5.4.1
[3+3]-CYCLOADDITION
WITH
NITRONES
152
5.4.2
[3+3]-CYCLOADDITION
WITH
PYRIDINIUM
YLIDES
AND
HYDRAZONES
155
5.4.3
DIASTEREOSELECTIVE
[3+3]-CYCLOADDITION
WITH
ACHIRAL
CATALYSTS
157
5.4.4
[3+3]-CYCLOADDITION
WITH
DIAZIRIDINES
158
5.4.5
[3+3]-CYCLOADDITION
WITH
DONOR-ACCEPTOR
CYCLOPROPANES
AND
OXIRANES
159
5.5
[3+4]-CYCLOADDITION
160
5.6
[3+5]-CYCLOADDITION
161
5.7
SUMMARY
162
REFERENCES
163
6
METAL-CATALYZED
DECARBENATIONS
BY
RETRO-CYCLOPROPANATION
169
MAURO
MATO
AND
ANTONIO
M.
ECHAVARREN
6.1
INTRODUCTION
169
6.2
REACTIVITY
AND
GENERATION
OF
METAL
CARBENES
169
6.2.1
DECOMPOSITION
OF
DIAZO
COMPOUNDS
170
6.2.2
ALTERNATIVE
METHODS
FOR
THE
GENERATION
OF
METAL
CARBENES
170
VIII
CONTENTS
6.2.3
DECARBENATION
REACTIONS:
GENERAL
PROCESS
AND
DEFINITION
170
6.3
RETRO-CYCLOPROPANATION
REACTIONS:
A
HISTORICAL
WALKTHROUGH
171
6.3.1
EARLY
OBSERVATIONS
171
6.3.2
DECARBENATION
REACTIONS
FROM
GAS
PHASE
TO
SOLUTION
173
6.3.3
THE
DISCOVERY
OF
THE
GOLD(I)-CATALYZED
RETRO-BUCHNER
REACTION
173
6.4
METAL-CATALYZED
AROMATIVE-DECARBENATION
REACTIONS:
A
MECHANISTIC
ANALYSIS
175
6.4.1
BASIC
MECHANISTIC
PICTURE
175
6.4.2
ALTERNATIVE
GENERATION
OF
THE
SAME
CARBENES
FROM
CARBENOIDS
175
6.4.3
THEORETICAL
STUDIES
ON
THE
MECHANISM
OF
THE
RETRO-BUCHNER
REACTION
177
6.4.4
SECOND-GENERATION
CYCLOHEPTATRIENES:
LOW
TEMPERATURE
AND
OTHER
METALS
179
6.4.5
MECHANISM
OF
THE
RH(II)-CATALYZED
AROMATIVE
DECARBENATION
181
6.5
SYNTHETIC
METHODOLOGIES
AND
APPLICATIONS
181
6.5.1
CYCLOPROPANATION
REACTIONS
181
6.5.1.1
ARYL
CYCLOPROPANATIONS
183
6.5.1.2
ALKENYL
CYCLOPROPANATIONS
184
6.5.1.3
REACTIONS
WITH
FURANS
185
6.5.2
HIGHER
FORMAL
CYCLOADDITIONS
186
6.5.2.1
(4+1)
CYCLOADDITIONS
187
6.5.2.2
(3+2)
CYCLOADDITIONS
187
6.5.2.3
(4+3)
CYCLOADDITIONS
189
6.5.3
INTRAMOLECULAR
FRIEDEL-CRAFTS
REACTIVITY
190
6.5.4
INSERTION
REACTIONS
190
6.5.4.1
C-H
INSERTION
190
6.5.4.2
SI-H
INSERTION
192
6.5.5
OXIDATION
REACTIONS
192
6.5.6
ALTERNATIVE
PRECURSORS
193
6.5.7
DECARBENATIONS
BASED
ON
THE
RELEASE
OF
ALKENES
193
6.6
GENERAL
OUTLOOK
AND
CONCLUDING
REMARKS
195
REFERENCES
196
7
GOLD-CATALYZED
OXIDATION
OF
ALKYNES
BY
N-OXIDES
OR
SULFOXIDES
199
KAYLAA
GUTMAN,
TIANYOU
LI,
AND
LIMING
ZHANG
7.1
INTRODUCTION:
GOLD-ACTIVATED
ALKYNES
ATTACKED
BY
NUCLEOPHILIC
OXIDANTS
199
7.2
SULFOXIDES
AS
NUCLEOPHILIC
OXIDANTS
201
7.3
N-OXIDES
AS
NUCLEOPHILIC
OXIDANTS
202
7.3.1
REACTIONS
OF
CARBENE/CARBENOID
INTERMEDIATES
WITH
OXYGEN-BASED
NUCLEOPHILES
205
7.3.2
REACTIONS
OF
CARBENE/CARBENOID
INTERMEDIATES
WITH
NITROGEN-BASED
NUCLEOPHILES
212
CONTENTS
IX
7.3.3
REACTIONS
OF
CARBENE/CARBENOID
INTERMEDIATES
WITH
OTHER
HETERONUCLEOPHILES
214
7.3.4
FRIEDEL-CRAFTS
REACTIONS
OF
CARBENE/CARBENOID
INTERMEDIATES
WITH
ARENES
215
7.3.5
REACTIONS
OF
CARBENE/CARBENOID
INTERMEDIATES
WITH
ALKENES
218
7.3.6
REACTIONS
OF
CARBENE/CARBENOID
INTERMEDIATES
WITH
C
-
C
TRIPLE
BONDS
224
7.3.7
1,2-C-C
AND
1,2-C-H
INSERTIONS
OF
CARBENE/CARBENOID
INTERMEDIATES
226
7.3.8
REMOTE
C(SP
3
)-H
FUNCTIONALIZATIONS
BY
CARBENE/CARBENOID
INTERMEDIATES
231
7.4
CONCLUSION
238
REFERENCES
238
8
TRANSITION-METAL-CATALYZED
CARBENE
TRANSFORMATIONS
FOR
POLYMER
SYNTHESES
243
EIJI
LHARA
AND
HIROAKI
SHIMOMOTO
8.1
INTRODUCTION
243
8.2
TRANSITION-METAL-CATALYZED
CL
POLYMERIZATION
OF
DIAZOACETATES
243
8.2.1
PDCL
2
-INITIATED
POLYMERIZATION
244
8.2.2
(NHC)PD(NQ)/BORATE-INITIATED
POLYMERIZATION
245
8.2.3
%-ALLYLPDCL-BASED
SYSTEM-INITIATED
POLYMERIZATION
246
8.2.4
(NQ)
2
PD/BORATE-
AND
(COD)PDCL(CL-NQ)/BORATE-INITIATED
POLYMERIZATION
251
8.2.5
PREPARATION
OF
POLYMERS
WITH
DENSELY
PACKED
FUNCTIONAL
GROUPS
AROUND
POLYMER
MAIN
CHAIN
254
8.2.5.1
HYDROXY
GROUP-CONTAINING
POLYMERS
254
8.2.5.2
OLIGO(OXYETHYLENE)-CONTAINING
POLYMERS
256
8.2.5.3
PYRENE-CONTAINING
POLYMERS
257
8.2.5.4
FLUOROALKYL
AND
FLUOROARYL
GROUP-CONTAINING
POLYMERS
258
8.3
POLYCONDENSATION
OF
BIS(DIAZOCARBONYL)
COMPOUNDS
259
8.3.1
THREE-COMPONENT
POLYCONDENSATION
OF
BIS(DIAZOCARBONYL)
COMPOUND,
DIOL,
AND
THF
259
8.3.2
THREE-COMPONENT
POLYCONDENSATION
OF
BIS(DIAZOCARBONYL)
COMPOUND,
DICARBOXYLIC
ACID,
AND
THF
262
8.3.3
THREE-COMPONENT
POLYCONDENSATION
OF
BIS(DIAZOCARBONYL)
COMPOUND,
ENOL-FORM
OF
1,3-DIKETONE,
AND
THF
263
8.3.4
TWO-COMPONENT
POLYCONDENSATION
OF
BIS(DIAZOCARBONYL)
COMPOUND
WITH
AROMATIC
DIAMINE
264
8.3.5
SINGLE-COMPONENT
POLYCONDENSATION
OF
BIS(DIAZOCARBONYL)
COMPOUND
TO
AFFORD
UNSATURATED
POLYESTERS
264
8.3.6
SINGLE-COMPONENT
POLYCONDENSATION
OF
BIS(DIAZOCARBONYL)
COMPOUND
TO
AFFORD
POLY(ARYLENE
VINYLENE)S
(PAV)
265
CONTENTS
8.4
CONCLUDING
REMARKS
266
REFERENCES
266
9
METAL-CATALYZED
QUINOID
CARBENE
(QC)
TRANSFER
REACTIONS
269
HAI-XU
WANG,
VANESSA
K.-Y.
LO,
AND
CHI-MING
CHE
9.1
INTRODUCTION
269
9.2
METAI-QUINOID
CARBENE
(QC)
COMPLEXES
AND
STOICHIOMETRIC
REACTIVITY
269
9.3
METAL-CATALYZED
QC
TRANSFER
REACTIONS
273
9.3.1
CYCLOPROPANATION
REACTIONS
273
9.3.2
C(SP
2
)-H
INSERTION
REACTIONS
275
9.3.3
C(SP
3
)-H
INSERTION
REACTIONS
284
9.3.4
NUCLEOPHILIC
ADDITION
AND
MISCELLANEOUS
REACTIONS
286
9.4
CONCLUSION
293
ACKNOWLEDGMENT
295
REFERENCES
295
10
ASYMMETRIC
REARRANGEMENT
AND
INSERTION
REACTIONS
WITH
METAL-CARBENOIDS
PROMOTED
BY
CHIRAL
N,N'-DIOXIDE
OR
GUANIDINE-BASED
CATALYSTS
299
XIAOBIN
LIN,
XIAOHUA
LIU,
AND
XIAOMING
FENG
10.1
INTRODUCTION
299
10.2
THE
INTRODUCTION
OF
CHIRAL
NJV'-DIOXIDE/METAL
COMPLEXES
AND
GUANIDINE
CATALYSTS
299
10.3
CHIRAL
N,N'-DIOXIDE/METAL
COMPLEXES-CATALYZED
REARRANGEMENT
REACTIONS
302
10.4
CHIRAL
GUANIDINE-BASED
CATALYST-MEDIATED
ASYMMETRIC
CARBENE
INSERTION
REACTIONS
315
10.5
CONCLUSION
AND
OUTLOOK
323
REFERENCES
323
11
MULTI-COMPONENT
REACTION
VIA
GEM-DIFUNCTIONALIZATION
OF
METAL
CARBENE
325
MENGCHU
ZHANG,
XINFANG
XU,
AND
WENHAO
HU
11.1
INTRODUCTION
325
11.2
MANNICH-TYPE
INTERCEPTION
327
11.2.1
INTERCEPTION
OF
AMMONIUM
YLIDE
327
11.2.2
INTERCEPTION
OF
OXONIUM
YLIDE
328
11.2.3
INTERCEPTION
OF
ZWITTERIONIC
INTERMEDIATE
339
11.3
ALDOL-TYPE
INTERCEPTION
340
11.3.1
INTERCEPTION
OF
AMMONIUM
YLIDE
340
11.3.2
INTERCEPTION
OF
OXONIUM
YLIDE
342
CONTENTS
XI
11.3.3
INTERCEPTION
OF
ZWITTERIONIC
INTERMEDIATE
343
11.4
MICHAEL-TYPE
INTERCEPTION
345
11.4.1
INTERCEPTION
OF
AMMONIUM
YLIDE
345
11.4.2
INTERCEPTION
OF
OXONIUM
YLIDE
346
11.4.3
INTERCEPTION
OF
ZWITTERIONIC
INTERMEDIATE
348
11.5
MISCELLANEOUS
TRANSFORMATIONS
349
11.5.1
INTERCEPTION
OTHER
TYPES
OF
ACTIVE
INTERMEDIATES
349
11.5.2
INTERCEPTION
OF
ACTIVE
INTERMEDIATES
WITH
OTHER
ELECTROPHILES
353
11.5.3
APPLICATIONS
IN
CASCADE
REACTIONS
355
11.6
SYNTHETIC
APPLICATIONS
358
11.6.1
SYNTHESIS
AND
M
ODIFICATION
OF
NATURAL
PRODUCTS
358
11.6.2
SYNTHESIS
OF
BIOACTIVE
MOLECULES
362
11.7
CONCLUSION
364
REFERENCES
365
12
TRANSITION-METAL-CATALYZED
CROSS-COUPLING
WITH
CARBENE
PRECURSORS
371
KANG
WANG
AND
JIANBO
WANG
12.1
INTRODUCTION
371
12.2
PALLADIUM-CATALYZED
CARBENE
CROSS-COUPLING REACTIONS
372
12.2.1
DIAZO
COMPOUNDS
AS
CARBENE
PRECURSORS
372
12.2.1.1
REACTIONS
WITH
ELECTROPHILES
372
12.2.1.2
REACTIONS
WITH
NUCLEOPHILES
373
12.2.1.3
PALLADIUM-CATALYZED
CASCADE
CROSS-COUPLING
REACTIONS
374
12.2.2
N-TOSYLHYDRAZONES
AS
CARBENE
PRECURSORS
377
12.2.2.1
REACTIONS
WITH
ELECTROPHILES
377
12.2.2.2
REACTIONS
WITH
NUCLEOPHILES
379
12.2.2.3
PALLADIUM-CATALYZED
CASCADE
CROSS-COUPLING
REACTIONS
380
12.2.3
NON-DIAZO
COMPOUNDS
AS
CARBENE
PRECURSORS
382
12.3
COPPER-CATALYZED
CARBENE
CROSS-COUPLING REACTIONS
385
12.3.1
REACTIONS
WITH
TERMINAL
ALKYNES
385
12.3.1.1
MULTI-SUBSTITUTED
ALLENES
AS
THE
COUPLING
PRODUCTS
385
12.3.1.2
INTERNAL
ALKYNES
AS
THE
COUPLING
PRODUCTS
386
12.3.2
REACTIONS
WITH
OTHER
COUPLING
PARTNERS
387
12.4
RHODIUM-CATALYZED
CARBENE
CROSS-COUPLING REACTIONS
388
12.4.1
GENERATING
ORGANORHODIUM
SPECIES
THROUGH
TRANSMETALATION
388
12.4.2
GENERATING
ORGANORHODIUM
SPECIES
THROUGH
C
-
C
BOND
CLEAVAGE
389
12.5
TRANSITION-METAL-CATALYZED
C
-
H
BOND
FUNCTIONALIZATIONS
WITH
CARBENE
PRECURSORS
391
12.5.1
NON-DIRECTING-GROUP-ASSISTED
C
-H
FUNCTIONALIZATIONS
391
12.5.2
DIRECTING-GROUP-ASSISTED
C
-
H
BOND
FUNCTIONALIZATIONS
393
12.5.2.1
GENERATING
ACYCLIC
PRODUCTS
THROUGH
C
-
H
BOND
ACTIVATION
393
12.5.2.2
GENERATING
CYCLIC
PRODUCTS
THROUGH
C
-H
BOND
ACTIVATION
394
XII
|
CONTENTS
12.6
CONCLUSION
REMARKS
396
ACKNOWLEDGMENT
397
REFERENCES
397
INDEX
401 |
| any_adam_object | 1 |
| any_adam_object_boolean | 1 |
| author2 | Wang, Jianbo 1962- Che, Chi-Ming Doyle, Michael P. 1942- |
| author2_role | edt edt edt |
| author2_variant | j w jw c m c cmc m p d mp mpd |
| author_GND | (DE-588)102580337X (DE-588)172047722 |
| author_facet | Wang, Jianbo 1962- Che, Chi-Ming Doyle, Michael P. 1942- |
| building | Verbundindex |
| bvnumber | BV047660185 |
| classification_rvk | VH 9700 VK 7000 VK 5550 |
| ctrlnum | (OCoLC)1306332646 (DE-599)DNB1238379613 |
| discipline | Chemie / Pharmazie |
| discipline_str_mv | Chemie / Pharmazie |
| format | Book |
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| genre | (DE-588)4143413-4 Aufsatzsammlung gnd-content |
| genre_facet | Aufsatzsammlung |
| id | DE-604.BV047660185 |
| illustrated | Illustrated |
| index_date | 2024-07-03T18:52:18Z |
| indexdate | 2024-07-10T09:18:33Z |
| institution | BVB |
| institution_GND | (DE-588)16179388-5 |
| isbn | 9783527347995 3527347992 |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-033045023 |
| oclc_num | 1306332646 |
| open_access_boolean | |
| owner | DE-11 DE-19 DE-BY-UBM |
| owner_facet | DE-11 DE-19 DE-BY-UBM |
| physical | xiv, 427 Seiten Illustrationen, Diagramme 24.4 cm x 17 cm |
| publishDate | 2022 |
| publishDateSearch | 2022 |
| publishDateSort | 2022 |
| publisher | Wiley-VCH |
| record_format | marc |
| spelling | Transition metal-catalyzed carbene transformations edited by Jianbo Wang, Chi-Ming Che and Michael P. Doyle Weinheim Wiley-VCH [2022] © 2022 xiv, 427 Seiten Illustrationen, Diagramme 24.4 cm x 17 cm txt rdacontent n rdamedia nc rdacarrier Katalyse (DE-588)4029921-1 gnd rswk-swf Carbene (DE-588)4147281-0 gnd rswk-swf Übergangsmetallkomplexe (DE-588)4131837-7 gnd rswk-swf Catalysis Chemie Chemistry Katalyse Organic Chemistry Organische Chemie Polymer Science & Technology Polymer Synthesis Polymersynthese Polymerwissenschaft u. -technologie CH40: Katalyse CH80: Organische Chemie PY30: Polymersynthese (DE-588)4143413-4 Aufsatzsammlung gnd-content Carbene (DE-588)4147281-0 s Katalyse (DE-588)4029921-1 s Übergangsmetallkomplexe (DE-588)4131837-7 s DE-604 Wang, Jianbo 1962- (DE-588)102580337X edt Che, Chi-Ming edt Doyle, Michael P. 1942- (DE-588)172047722 edt Wiley-VCH (DE-588)16179388-5 pbl Erscheint auch als Online-Ausgabe, PDF 978-3-527-82916-3 Erscheint auch als Online-Ausgabe, ePub 978-3-527-82915-6 Erscheint auch als Online-Ausgabe, oBook 978-3-527-82917-0 X:MVB http://www.wiley-vch.de/publish/dt/books/ISBN978-3-527-34799-5/ Beschreibung für Leser DNB Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=033045023&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Transition metal-catalyzed carbene transformations Katalyse (DE-588)4029921-1 gnd Carbene (DE-588)4147281-0 gnd Übergangsmetallkomplexe (DE-588)4131837-7 gnd |
| subject_GND | (DE-588)4029921-1 (DE-588)4147281-0 (DE-588)4131837-7 (DE-588)4143413-4 |
| title | Transition metal-catalyzed carbene transformations |
| title_auth | Transition metal-catalyzed carbene transformations |
| title_exact_search | Transition metal-catalyzed carbene transformations |
| title_exact_search_txtP | Transition metal-catalyzed carbene transformations |
| title_full | Transition metal-catalyzed carbene transformations edited by Jianbo Wang, Chi-Ming Che and Michael P. Doyle |
| title_fullStr | Transition metal-catalyzed carbene transformations edited by Jianbo Wang, Chi-Ming Che and Michael P. Doyle |
| title_full_unstemmed | Transition metal-catalyzed carbene transformations edited by Jianbo Wang, Chi-Ming Che and Michael P. Doyle |
| title_short | Transition metal-catalyzed carbene transformations |
| title_sort | transition metal catalyzed carbene transformations |
| topic | Katalyse (DE-588)4029921-1 gnd Carbene (DE-588)4147281-0 gnd Übergangsmetallkomplexe (DE-588)4131837-7 gnd |
| topic_facet | Katalyse Carbene Übergangsmetallkomplexe Aufsatzsammlung |
| url | http://www.wiley-vch.de/publish/dt/books/ISBN978-3-527-34799-5/ http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=033045023&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT wangjianbo transitionmetalcatalyzedcarbenetransformations AT chechiming transitionmetalcatalyzedcarbenetransformations AT doylemichaelp transitionmetalcatalyzedcarbenetransformations AT wileyvch transitionmetalcatalyzedcarbenetransformations |