Methodologies in amine synthesis: challenges and applications
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| Language: | English |
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Weinheim
Wiley-VCH
[2021]
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| Subjects: | |
| Online Access: | Kurzbeschreibung Inhaltsverzeichnis |
| Item Description: | Literaturangaben |
| Physical Description: | xiii, 460 Seiten Illustrationen (teilweise farbig) |
| ISBN: | 9783527347391 |
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| 016 | 7 | |a 1211570495 |2 DE-101 | |
| 020 | |a 9783527347391 |c hbk. |9 978-3-527-34739-1 | ||
| 035 | |a (OCoLC)1249683666 | ||
| 035 | |a (DE-599)DNB1211570495 | ||
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| 084 | |a VK 7400 |0 (DE-625)147419:253 |2 rvk | ||
| 245 | 1 | 0 | |a Methodologies in amine synthesis |b challenges and applications |c edited by Alfredo Ricci and Luca Bernadi |
| 264 | 1 | |a Weinheim |b Wiley-VCH |c [2021] | |
| 264 | 4 | |c © 2021 | |
| 300 | |a xiii, 460 Seiten |b Illustrationen (teilweise farbig) | ||
| 336 | |b txt |2 rdacontent | ||
| 337 | |b n |2 rdamedia | ||
| 338 | |b nc |2 rdacarrier | ||
| 500 | |a Literaturangaben | ||
| 650 | 0 | 7 | |a Amine |0 (DE-588)4001705-9 |2 gnd |9 rswk-swf |
| 650 | 0 | 7 | |a Chemische Synthese |0 (DE-588)4133806-6 |2 gnd |9 rswk-swf |
| 653 | |a Amine | ||
| 653 | |a Catalysis | ||
| 653 | |a Chemie | ||
| 653 | |a Chemistry | ||
| 653 | |a Industrial Chemistry | ||
| 653 | |a Katalyse | ||
| 653 | |a Materials Science | ||
| 653 | |a Materialwissenschaften | ||
| 653 | |a Organic Chemistry | ||
| 653 | |a Organische Chemie | ||
| 653 | |a Technische u. Industrielle Chemie | ||
| 653 | |a CH30: Technische u. Industrielle Chemie | ||
| 653 | |a CH40: Katalyse | ||
| 653 | |a CH80: Organische Chemie | ||
| 653 | |a MS00: Allg. Materialwissenschaften | ||
| 655 | 7 | |0 (DE-588)4143413-4 |a Aufsatzsammlung |2 gnd-content | |
| 689 | 0 | 0 | |a Amine |0 (DE-588)4001705-9 |D s |
| 689 | 0 | 1 | |a Chemische Synthese |0 (DE-588)4133806-6 |D s |
| 689 | 0 | |5 DE-604 | |
| 700 | 1 | |a Ricci, Alfredo |0 (DE-588)1233695614 |4 edt | |
| 700 | 1 | |a Bernardi, Luca |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 978-3-527-82617-9 |
| 776 | 0 | 8 | |i Erscheint auch als |n Online-Ausgabe, EPUB |z 978-3-527-82619-3 |
| 776 | 0 | 8 | |i Erscheint auch als |n Online-Ausgabe, oBook |z 978-3-527-82618-6 |
| 856 | 4 | 2 | |m X:MVB |u http://www.wiley-vch.de/publish/dt/books/ISBN978-3-527-34739-1/ |3 Kurzbeschreibung |
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| 999 | |a oai:aleph.bib-bvb.de:BVB01-032295674 | ||
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| adam_text | V
CONTENTS
PREFACE
XI
1
SUBSTITUTION-TYPE
ELECTROPHILIC
AMINATION
USING
HYDROXYLAMINE-DERIVED
REAGENTS
1
ZHE
ZHOU
AND
LASZLO
KURTI
1.1
INTRODUCTION
1
1.2
CU-CATALYZED
REACTIONS
2
1.3
ELECTROPHILIC
AMINATION
REACTIONS
CATALYZED
BY
OTHER
TRANSITION
METALS
15
1.4
ELECTROPHILIC
AMINATION
WITH
HYDROXYLAMINE-DERIVED
METALLANITRENES
18
1.5
TRANSITION-METAL-FREE
ELECTROPHILIC
AMINATION
REACTIONS
22
1.6
CONCLUSION
28
REFERENCES
28
2
REMOTE
FUNCTIONALIZATIONS
USING
NITROGEN
RADICALS
IN
H-ATOM
TRANSFER
(HAT)
REACTIONS
31
JI
HYE
KIM,
ELIZABETH
M.
DAUNCEY
AND
DANIELE
LEONORI
2.1
INTRODUCTION
31
2.2
INTRAMOLECULAR
1
,5-H-ATOM
TRANSFER
(1
,5-HAT)
31
2.3
PHOTOINDUCED
STRATEGIES
34
2.3.1
REDUCTIVE
STRATEGIES
34
2.3.1.1
1,5-HAT
VIA
IMINYL
RADICALS
34
23.1.2
1,5-HAT
VIA
AMIDYL
AND
SULFAMIDYL
RADICALS
37
2.3.2
OXIDATIVE
STRATEGIES
39
23.2.1
1,5-HAT
VIA
IMINYL
RADICALS
39
23.2.2
1,5-HAT
VIA
AMIDYL
AND
SULFAMIDYL
RADICALS
40
2.3.3
PHOTOINDUCED
BOND
HOMOLYSIS
43
2.4
THERMAL
STRATEGIES
46
2.5
SUMMARY
AND
CONCLUSIONS
50
REFERENCES
50
VI
CONTENTS
3
RADICAL-BASED
C-N
BOND
FORMATION
IN
PHOTO/ELECTROCHEMISTRY
53
BINBIN
HUANG,
YATING
ZHAO
AND
WUJIONG
XIA
3.1
INTRODUCTION
53
3.2
C
*
N
BOND
FORMATION
VIA
N-RADICAL
SPECIES
ADDITION
54
3.2.1
RADICAL
ADDITION
TO
C
*
C
DOUBLE/TRIPLE
BONDS
55
3.2.1.1
AMIDYL
RADICAL
ADDITION
55
3.2.1.2
HYDRAZONYL
RADICAL
ADDITION
62
3.2.1.3
AMINIUM
RADICAL
CATION
ADDITION
64
3.2.2
RADICAL
SPECIES
ADDITION
TO
AROMATIC
RINGS
71
3.3
AMINATION
VIA
N-ATOM
NUCLEOPHILIC
ADDITION
77
3.3.1
AROMATIC
C(SP
2
)
*
H
BOND
AMINATION
77
3.3.2
OLEFINIC
C(SP
2
)
*
H
BOND
AMINATION
82
3.3.3
ACTIVATED
C(SP
3
)
*H
BOND
AMINATION
85
3.3.3.1
BENZYLIC
C(SP
3
)
*
H
BOND
AMINATION
85
33.3.2
N-A-C(SP
3
)
*H
BOND
AMINATION
87
3.4
AMINATION
VIA
RADICAL
CROSS-COUPLING
90
3.4.1
ARYL
C(SP
2
)*
N
BOND
FORMATION
VIA
RADICAL
CROSS-COUPLING
90
3.4.1.1
ARYL
C(SP
2
)
*
N
BOND
FORMATION
USING
DIARYLAMINES
91
3.4.1.2
ARYL
C(SP
2
)
*N
BOND
FORMATION
USING
AZOLES
94
3.4.2
OTHER
C
*
N
BOND
FORMATION
VIA
RADICAL
CROSS-COUPLING
96
3.5
SUMMARY
AND
CONCLUSIONS
98
REFERENCES
100
4
PROPARGYLAMINES:
RECENT
ADVANCES
IN
ASYMMETRIC
SYNTHESIS
AND
USE
AS
CHEMICAL
TOOLS
IN
ORGANIC
CHEMISTRY
103
FEI
ZHAO,
SEONG-HEUN
KIM
AND
DANIELE
CASTAGNOLO
4.1
INTRODUCTION
103
4.2
METAL-CATALYZED
ASYMMETRIC
SYNTHESIS
OF
PROPARGYLAMINES
104
4.2.1
ENANTIOSELECTIVE
A
3
COUPLING
104
4.2.1.1
ENANTIOSELECTIVE
A
3
COUPLING
INVOLVING
PRIMARY
AMINES
106
4.2.1.2
ENANTIOSELECTIVE
A
3
COUPLING
INVOLVING
SECONDARY
AMINES
108
4.2.2
ENANTIOSELECTIVE
PROPARGYLIC
AMINATION
OF
PROPARGYLIC
ESTERS
WITH
AMINES
112
4.2.3
CU-CATALYZED
ENANTIOSELECTIVE
RING
OPENING
OF
ALKYNYL-SUBSTITUTED
EPOXIDES/LACTONES/CARBONATES
116
4.2.4
ENANTIOSELECTIVE
ADDITION
OF
TERMINAL
ALKYNES
TO
ENAMINES/ENAMIDES
118
4.2.5
RH/RU-CATALYZED
ENANTIOSELECTIVE
HYDROGENATION
OF
ALKYNYL-SUBSTITUTED
ENAMIDES/IMINES
120
4.2.6
ENANTIOSELECTIVE
C-H
ACTIVATION:
SYNTHESIS
OF
CYCLIC
PROPARGYLAMINES
123
4.3
ENZYMATIC
SYNTHESIS
OF
PROPARGYLAMINES
126
4.4
PHOTOREDOX
SYNTHESIS
OF
PROPARGYLAMINES
130
4.5
ORGANOCATALYZED
ASYMMETRIC
SYNTHESIS
OF
PROPARGYLAMINES
134
4.6
PROPARGYLAMINES
AS
BUILDING
BLOCKS
IN
THE
SYNTHESIS
OF
HETEROCYCLES
137
4.6.1
SYNTHESIS
OF
PYRROLES
FROM
PROPARGYLAMINES
138
4.6.2
SYNTHESIS
OF
PYRROLINES
FROM
PROPARGYLAMINES
139
CONTENTS
VII
4.6.3
4.6.4
4.6.5
4.6.6
4.7
SYNTHESIS
OF
PYRIDINES
FROM
PROPARGYLAMINES
140
SYNTHESIS
OF
QUINOLINES
FROM
PROPARGYLAMINES
142
SYNTHESIS
OF
OXAZOLES
FROM
PROPARGYLAMINES
145
SYNTHESIS
OF
THIAZOLES
FROM
PROPARGYLAMINES
148
CONCLUSIONS
150
REFERENCES
150
5
TRANSITION-METAL-CATALYZED
CHIRAL
AMINES
SYNTHESIS
155
ANTON
CUNILLERA,
CARMEN
CLOVER,
CYRIL
GODARD,
MARTINE
URRUTIGOTTY
AND
PHILIPPE
KALCK
5.1
5.2
5.3
5.4
5.5
5.6
5.7
INTRODUCTION
155
ASYMMETRIC
REDUCTIVE
AMINATION
156
ASYMMETRIC
HYDROAMINATION
162
ASYMMETRIC
HYDROAMINOALKYLATION
168
ASYMMETRIC
HYDROAMINOMETHYLATION
171
COUPLING
ON
A
CHIRAL
METAL
CENTER
176
CONCLUSION
177
REFERENCES
178
6
INDUSTRIAL
RELEVANCE
OF
ASYMMETRIC
ORGANOCATALYSIS
IN
THE
PREPARATION
OF
CHIRAL
AMINE
DERIVATIVES
187
LUCA
BERNARDI,
ARMANDO
CARLONE
AND
FRANCESCO
FINI
6.1
6.2
6.3
6.3.1
6.3.1.1
6.3.1.2
6.3.1.3
6.3.2
6.3.3
6.4
INTRODUCTION
187
ORGANOCATALYSIS
IN
MANUFACTURE:
REPRESENTATIVE
EXAMPLES
189
CASE
STUDIES
200
PREGABALIN
200
PATHWAY
A:
DESYMMETRIZATION
OF
GLUTARIC
ANHYDRIDE
53
202
PATHWAY
B:
ADDITION
OF
AN
AMINO
A-CARBANION
55
TO
MICHAEL
ACCEPTORS
204
PATHWAY
C:
ADDITION
OF
ACETATE
ENOLATE
EQUIVALENTS
TO
NITROALKENE
56
206
BICYCLIC
A-AMINO
ACID
CORE
OF
TELAPREVIR
214
5-(TRIFLUOROMETHYL)-2-ISOXAZOLINES
AS
ANTIPEST
AGENTS
223
SUMMARY
AND
CONCLUSIONS
230
REFERENCES
231
7
BIOCATALYTIC
SYNTHESIS
OF
CHIRAL
AMINES
USING
OXIDOREDUCTASES
243
SEBASTIAN
C.
COSGROVE,
JEREMY
/.
RAMSDEN,
JUAN
MANGAS-SANCHEZ
AND
NICHOLAS
J,
TURNER
7.1
7.2
7.2.1
7.2.2
7.2.2.1
7.2.2.2
7.2.2.3
7.2.2.4
INTRODUCTION
243
AMINE
OXIDASES
243
INTRODUCTION
243
(S)-SELECTIVE
AMINE
OXIDASES
244
MONOAMINE
OXIDASE
FROM
ASPERGILLUS
NIGER
244
DIRECTED
EVOLUTION
OF
MAO-N
244
SYNTHETIC
APPLICATIONS
AND
CASCADES
247
MONOAMINE
OXIDASE
FROM
PSEUDOMONAS
MONTEILII
ZMU-T01
249
VIII
|
CONTENTS
7.2.2.5
CYCLOHEXYLAMINE
OXIDASE
FROM
BREVIBACTERIUM
OXYDANS
(CHAO)
249
7.2.3
(R)-SELECTIVE
AMINE
OXIDASES
252
7.2.3.1
D-AMINO
ACID
OXIDASE
(PKDAO)
252
7.2.3.2
6-HYDROXY-D-NICOTINE
OXIDASE
(6-HDNO)
FROM
ARTHROBACTER
NICOTINOVORANS
252
7.3
AMINE
DEHYDROGENASES
252
7.3.1
INTRODUCTION
252
7.3.2
DISCOVERY
AND
ENGINEERING
OF
AMDH
253
7.3.2.1
LEUCINE
DEHYDROGENASE
253
7.3.2.2
PHENYLALANINE
DEHYDROGENASE
AND
CHIMERIC
AMINE
DEHYDROGENASE
254
7.3.2.3
NATIVE
AMINE
DEHYDROGENASE
254
7.3.3
SYNTHETIC
APPLICATIONS
OF
AMDH
256
7.3.3.1
PRIMARY
AMINE
SYNTHESIS
WITH
ENGINEERED
AMDH
256
7.3.3.2
PRIMARY
AMINE
SYNTHESIS
WITH
NATURAL
AMDH
258
7.3.3.3
SUBSTRATE
PROMISCUITY
IN
AMDH
259
7.3.3
A
CASCADE
REACTIONS
THAT
USE
AMDH
260
7.4
IMINE
REDUCTASES
262
7.4.1
FROM
BIOSYNTHESIS
TO
BIOCATALYSIS
262
7A.2
BIOCATALYTIC
APPLICATION
OF
IMINE
REDUCTASES
264
7.4.2.1
IREDS
IN
CASCADE
AND
CHEMOENZYMATIC
SYNTHESIS
265
7.4.3
IRED
ENGINEERING
267
7.4.4
IMINE
REDUCTASES
CATALYZING
REDUCTIVE
AMINATION
267
7.4.5
IMINE
REDUCTASE-CATALYZED
AMINE
ALKYLATION
CASCADES
270
7.4.6
ENGINEERING
OF
REDUCTIVE
AMINASES
270
7.5
ENGINEERED
CYTOCHROME
P450S
270
7.6
CONCLUSIONS
AND
PERSPECTIVES
274
REFERENCES
274
8
ENGINEERING
FUNCTIONAL
NANOMATERIALS
THROUGH
THE
AMINO
GROUP
285
GIACOMO
FILIPPINI,
PAOLO
PENGO,
SUSANNA
BOSI,
GIULIO
RAGAZZON,
LUCIA
PASQUATO
AND
MAURIZIO
PRATO
8.1
ABBREVIATIONS
285
8.1
INTRODUCTION
287
8.2
QUANTIFICATION
OF
NANOMATERIAL-BOUND
AMINO
GROUPS
288
8.3
EXPLOITING
AMINO
COMPOUNDS
FOR
THE
FUNCTIONALIZATION
OF
CARBON-BASED
NANOMATERIALS
290
8.3.1
HISTORICAL
BACKGROUNDS:
ALLOTROPES
OF
CARBON
290
8.3.2
USE
OF
AMINES
FOR
THE
FUNCTIONALIZATION
OF
CARBON
NANOSTRUCTURES
290
8.3.3
OTHER
FUNCTIONALIZATION
PROCEDURES
OF
COMMON
CARBON
NANOSTRUCTURES
297
8.3.4
EXFOLIATION
OF
GRAPHITE
WITH
MELAMINE
299
8.3.5
OTHER
CARBON
NANOMATERIALS
301
8.3.5.1
CARBON
NANOHORNS
301
8.3.5.2
CARBON
NANODIAMONDS
305
8.3.5.3
CARBON
NANO-ONIONS
307
CONTENTS
IX
8.3.6
AMINO-FUNCTIONALIZED
CARBON-BASED
NANOMATERIALS
FOR
ANALYTICAL
APPLICATIONS
308
8.4
AMINES
IN
THE
SYNTHESIS
AND
FUNCTIONALIZATION
OF
CARBON
DOTS
309
8.4.1
AMINES
AS
CD
CONSTITUENTS
310
8.4.2
AMINE-RICH
CDS
FROM
ARGININE
AND
ETHYLENEDIAMINE
(NCDS)
312
8.4.2.1
ONE-POT
FUNCTIONALIZATION
OF
NCDS
312
8.4.2.2
POSTFUNCTIONALIZATION
OF
NCDS
313
8.4.2.3
USE
OF
CD-SUPPORTED
AMINES
IN
ORGANOCATALYSIS
315
8.5
AMINES
FOR
THE
ENGINEERING
OF
HYBRID
ORGANIC-INORGANIC
NANOMATERIALS
316
8.5.1
AMINES
AS
HEAD
GROUPS
OR
END
GROUPS
ON
SELF-ASSEMBLED
MONOLAYERS
ON
FLAT
SURFACES
316
8.5.2
ALKYLAMINES
IN
THE
PREPARATION
OF
SEMICONDUCTOR
QUANTUM
DOTS
319
8.5.2.1
SULFUR-AMINE
AND
SELENIUM-AMINE
SYSTEMS
319
8.5.2.2
CAPPING
LIGANDS
FOR
QUANTUM
DOTS
AND
LIGAND
EXCHANGE
BY
AMINES
321
8.5.3
ALKYLAMINES
AS
REAGENTS
FOR
THE
SYNTHESIS
AND
PASSIVATION
OF
METAL
NANOPARTICLES
322
8.5.3.1
ALKYLAMINES
AS
CAPPING
AGENTS
FOR
METAL
NANOPARTICLES
322
8.5.3.2
DISPLACEMENT
OF
AMINES
FROM
THE
SURFACE
OF
METAL
NANOPARTICLES
325
8.5.4
AMINES
ON
THE
OUTER
SURFACE
OF
ORGANIC-INORGANIC
HYBRID
NANOPARTICLES
325
8.5.5
POSTFUNCTIONALIZATION
OF
AMINE-TERMINATED
ORGANIC-INORGANIC
HYBRID
NANOPARTICLES
328
REFERENCES
329
9
RECENT
ADVANCES
IN
THE
SYNTHESIS
OF
NITROGEN
COMPOUNDS
FROM
BIOMASS
DERIVATIVES
341
ANA
C.
FERNANDES
9.1
INTRODUCTION
341
9.2
SYNTHESIS
OF
NITROGEN
COMPOUNDS
FROM
CHITIN
AND
ITS
DERIVATIVES
341
9.3
SYNTHESIS
OF
AMINES
AND
FORMAMIDES
FROM
A-AMINO
ACIDS
345
9.4
SYNTHESIS
OF
NITROGEN
COMPOUNDS
FROM
CELLULOSIC
BIOMASS
DERIVATIVES
348
9.5
SYNTHESIS
OF
NITROGEN
COMPOUNDS
FROM
LIGNIN
DERIVATIVES
366
9.6
SYNTHESIS
OF
NITROGEN
COMPOUNDS
FROM
TRIGLYCERIDES
AND
FATTY
ALCOHOLS
370
9.7
CONCLUSION
373
REFERENCES
373
10
RECENT
ADVANCES
IN
THE
SYNTHESIS
OF
ARYLAMINES
IN
THE
LIGHT
OF
APPLICATION
IN
PHARMACEUTICAL
AND
CHEMICAL
INDUSTRY
377
DINO
BERTHOLD,
ALEXANDER
M.
HAYDL,
JOYCE
C.
LEUNG,
ULRICH
SCHOLZ,
QING
XIAO
AND
ZHIBIN
ZHU
10.1
MODERN
APPROACHES
TO
TRANSITION-METAL-CATALYZED
C-N
COUPLING
IN
INDUSTRY
377
10.1.1
INTRODUCTION
377
10.1.2
TRANSITION-METAL-CATALYZED
C
*N-BOND
FORMATION
377
10.1.2.1
ULLMANN-IYPE
AMINATION
378
10.1.2.2
BUCHWALD-HARTWIG
AMINATION
383
CONTENTS
10.2
NEW
METHODOLOGIES
IN
THE
SYNTHESIS
OF
ARYLAMINES
ON
THE
BRINK
OF
INDUSTRIAL
APPLICATION
388
10.2.1
INTRODUCTION
388
10.2.2
CATALYTIC
C-H
AMINATION
389
10.2.2.1
CATALYTIC
C-H
AMINATION
UNDER
STANDARD
CONDITIONS
389
10.2.2.2
PHOTOREDOX
CATALYSIS
399
10.2.2.3
ELECTROCHEMICAL
APPROACHES
402
10.2.3
DECARBOXYLATIVE
ARYL
AMINATION
405
10.2.4
NICKEL-CATALYZED
C-N
COUPLING
407
10.2.5
OTHER
METAL-CATALYZED
CROSS-COUPLINGS
414
10.2.6
REDUCTIVE
AMINATION
417
10.2.7
HYDROAMINATION
419
10.2.8
SUMMARY
AND
CONCLUSIONS
424
10.3
ADVANCES
TO
ARYLAMINE
FORMATION
USING
INTENSIFIED
AND
MORE
SUSTAINABLE
PROCESS
TECHNOLOGIES
424
10.3.1
INTRODUCTION
424
10.3.2
FLOW
CHEMISTRY
425
10.3.2.1
PD-CATALYZED
C
*
N
BOND
FORMING
REACTION
425
10.3.2.2
NUCLEOPHILIC
AROMATIC
SUBSTITUTION
426
10.3.2.3
TELESCOPED
SEQUENCE
OF
NITRATION
AND
HYDROGENATION
IN
FLOW
SYNTHESIS
428
10.3.2.4
CHAN-LAM
COUPLING
428
10.3.3
IMMOBILIZATION
OF
CATALYSTS/SUPPORTED
CATALYSTS
429
10.3.4
PERSONAL
ACCOUNTS
FROM
CONTRACT MANUFACTURING
COMPANIES
ON
UTILITY
OF
MODERN
FLOW
AMINATION
METHODS
431
10.4
MISCELLANEOUS
ASPECTS
OF
AROMATIC
AMINATION
REACTIONS
IN
THE
WORLD
OF
ACTIVE
PHARMACEUTICAL
INGREDIENTS
431
10.4.1
COHORT
OF
CONCERNS
AND
ITS
REGULATORY
IMPACT
ON
AMINE-BASED
ACTIVE
PHARMACEUTICAL
COMPOUNDS
431
10.4.2
ROLE
OF
CONTROL
OF
ELEMENTAL
IMPURITIES
IN
HUMAN
PHARMA
APPLICATIONS
432
10.4.3
TRANSITION
METAL
ACCOUNTING
433
10.4.4
RECYCLING
OF
METALS,
LIGANDS,
AND
OTHER
COST
DRIVERS
OF
AROMATIC
AMINATION
434
10.4.5
REGULATORY
REQUIREMENTS
FOR
THE
SUBMISSION
OF
A
CATALYTIC
REACTION
IN A
NEW
DRUG
APPLICATION
434
REFERENCES
435
INDEX
445
|
| adam_txt |
V
CONTENTS
PREFACE
XI
1
SUBSTITUTION-TYPE
ELECTROPHILIC
AMINATION
USING
HYDROXYLAMINE-DERIVED
REAGENTS
1
ZHE
ZHOU
AND
LASZLO
KURTI
1.1
INTRODUCTION
1
1.2
CU-CATALYZED
REACTIONS
2
1.3
ELECTROPHILIC
AMINATION
REACTIONS
CATALYZED
BY
OTHER
TRANSITION
METALS
15
1.4
ELECTROPHILIC
AMINATION
WITH
HYDROXYLAMINE-DERIVED
METALLANITRENES
18
1.5
TRANSITION-METAL-FREE
ELECTROPHILIC
AMINATION
REACTIONS
22
1.6
CONCLUSION
28
REFERENCES
28
2
REMOTE
FUNCTIONALIZATIONS
USING
NITROGEN
RADICALS
IN
H-ATOM
TRANSFER
(HAT)
REACTIONS
31
JI
HYE
KIM,
ELIZABETH
M.
DAUNCEY
AND
DANIELE
LEONORI
2.1
INTRODUCTION
31
2.2
INTRAMOLECULAR
1
,5-H-ATOM
TRANSFER
(1
,5-HAT)
31
2.3
PHOTOINDUCED
STRATEGIES
34
2.3.1
REDUCTIVE
STRATEGIES
34
2.3.1.1
1,5-HAT
VIA
IMINYL
RADICALS
34
23.1.2
1,5-HAT
VIA
AMIDYL
AND
SULFAMIDYL
RADICALS
37
2.3.2
OXIDATIVE
STRATEGIES
39
23.2.1
1,5-HAT
VIA
IMINYL
RADICALS
39
23.2.2
1,5-HAT
VIA
AMIDYL
AND
SULFAMIDYL
RADICALS
40
2.3.3
PHOTOINDUCED
BOND
HOMOLYSIS
43
2.4
THERMAL
STRATEGIES
46
2.5
SUMMARY
AND
CONCLUSIONS
50
REFERENCES
50
VI
CONTENTS
3
RADICAL-BASED
C-N
BOND
FORMATION
IN
PHOTO/ELECTROCHEMISTRY
53
BINBIN
HUANG,
YATING
ZHAO
AND
WUJIONG
XIA
3.1
INTRODUCTION
53
3.2
C
*
N
BOND
FORMATION
VIA
N-RADICAL
SPECIES
ADDITION
54
3.2.1
RADICAL
ADDITION
TO
C
*
C
DOUBLE/TRIPLE
BONDS
55
3.2.1.1
AMIDYL
RADICAL
ADDITION
55
3.2.1.2
HYDRAZONYL
RADICAL
ADDITION
62
3.2.1.3
AMINIUM
RADICAL
CATION
ADDITION
64
3.2.2
RADICAL
SPECIES
ADDITION
TO
AROMATIC
RINGS
71
3.3
AMINATION
VIA
N-ATOM
NUCLEOPHILIC
ADDITION
77
3.3.1
AROMATIC
C(SP
2
)
*
H
BOND
AMINATION
77
3.3.2
OLEFINIC
C(SP
2
)
*
H
BOND
AMINATION
82
3.3.3
ACTIVATED
C(SP
3
)
*H
BOND
AMINATION
85
3.3.3.1
BENZYLIC
C(SP
3
)
*
H
BOND
AMINATION
85
33.3.2
N-A-C(SP
3
)
*H
BOND
AMINATION
87
3.4
AMINATION
VIA
RADICAL
CROSS-COUPLING
90
3.4.1
ARYL
C(SP
2
)*
N
BOND
FORMATION
VIA
RADICAL
CROSS-COUPLING
90
3.4.1.1
ARYL
C(SP
2
)
*
N
BOND
FORMATION
USING
DIARYLAMINES
91
3.4.1.2
ARYL
C(SP
2
)
*N
BOND
FORMATION
USING
AZOLES
94
3.4.2
OTHER
C
*
N
BOND
FORMATION
VIA
RADICAL
CROSS-COUPLING
96
3.5
SUMMARY
AND
CONCLUSIONS
98
REFERENCES
100
4
PROPARGYLAMINES:
RECENT
ADVANCES
IN
ASYMMETRIC
SYNTHESIS
AND
USE
AS
CHEMICAL
TOOLS
IN
ORGANIC
CHEMISTRY
103
FEI
ZHAO,
SEONG-HEUN
KIM
AND
DANIELE
CASTAGNOLO
4.1
INTRODUCTION
103
4.2
METAL-CATALYZED
ASYMMETRIC
SYNTHESIS
OF
PROPARGYLAMINES
104
4.2.1
ENANTIOSELECTIVE
A
3
COUPLING
104
4.2.1.1
ENANTIOSELECTIVE
A
3
COUPLING
INVOLVING
PRIMARY
AMINES
106
4.2.1.2
ENANTIOSELECTIVE
A
3
COUPLING
INVOLVING
SECONDARY
AMINES
108
4.2.2
ENANTIOSELECTIVE
PROPARGYLIC
AMINATION
OF
PROPARGYLIC
ESTERS
WITH
AMINES
112
4.2.3
CU-CATALYZED
ENANTIOSELECTIVE
RING
OPENING
OF
ALKYNYL-SUBSTITUTED
EPOXIDES/LACTONES/CARBONATES
116
4.2.4
ENANTIOSELECTIVE
ADDITION
OF
TERMINAL
ALKYNES
TO
ENAMINES/ENAMIDES
118
4.2.5
RH/RU-CATALYZED
ENANTIOSELECTIVE
HYDROGENATION
OF
ALKYNYL-SUBSTITUTED
ENAMIDES/IMINES
120
4.2.6
ENANTIOSELECTIVE
C-H
ACTIVATION:
SYNTHESIS
OF
CYCLIC
PROPARGYLAMINES
123
4.3
ENZYMATIC
SYNTHESIS
OF
PROPARGYLAMINES
126
4.4
PHOTOREDOX
SYNTHESIS
OF
PROPARGYLAMINES
130
4.5
ORGANOCATALYZED
ASYMMETRIC
SYNTHESIS
OF
PROPARGYLAMINES
134
4.6
PROPARGYLAMINES
AS
BUILDING
BLOCKS
IN
THE
SYNTHESIS
OF
HETEROCYCLES
137
4.6.1
SYNTHESIS
OF
PYRROLES
FROM
PROPARGYLAMINES
138
4.6.2
SYNTHESIS
OF
PYRROLINES
FROM
PROPARGYLAMINES
139
CONTENTS
VII
4.6.3
4.6.4
4.6.5
4.6.6
4.7
SYNTHESIS
OF
PYRIDINES
FROM
PROPARGYLAMINES
140
SYNTHESIS
OF
QUINOLINES
FROM
PROPARGYLAMINES
142
SYNTHESIS
OF
OXAZOLES
FROM
PROPARGYLAMINES
145
SYNTHESIS
OF
THIAZOLES
FROM
PROPARGYLAMINES
148
CONCLUSIONS
150
REFERENCES
150
5
TRANSITION-METAL-CATALYZED
CHIRAL
AMINES
SYNTHESIS
155
ANTON
CUNILLERA,
CARMEN
CLOVER,
CYRIL
GODARD,
MARTINE
URRUTIGOTTY
AND
PHILIPPE
KALCK
5.1
5.2
5.3
5.4
5.5
5.6
5.7
INTRODUCTION
155
ASYMMETRIC
REDUCTIVE
AMINATION
156
ASYMMETRIC
HYDROAMINATION
162
ASYMMETRIC
HYDROAMINOALKYLATION
168
ASYMMETRIC
HYDROAMINOMETHYLATION
171
COUPLING
ON
A
CHIRAL
METAL
CENTER
176
CONCLUSION
177
REFERENCES
178
6
INDUSTRIAL
RELEVANCE
OF
ASYMMETRIC
ORGANOCATALYSIS
IN
THE
PREPARATION
OF
CHIRAL
AMINE
DERIVATIVES
187
LUCA
BERNARDI,
ARMANDO
CARLONE
AND
FRANCESCO
FINI
6.1
6.2
6.3
6.3.1
6.3.1.1
6.3.1.2
6.3.1.3
6.3.2
6.3.3
6.4
INTRODUCTION
187
ORGANOCATALYSIS
IN
MANUFACTURE:
REPRESENTATIVE
EXAMPLES
189
CASE
STUDIES
200
PREGABALIN
200
PATHWAY
A:
DESYMMETRIZATION
OF
GLUTARIC
ANHYDRIDE
53
202
PATHWAY
B:
ADDITION
OF
AN
AMINO
A-CARBANION
55
TO
MICHAEL
ACCEPTORS
204
PATHWAY
C:
ADDITION
OF
ACETATE
ENOLATE
EQUIVALENTS
TO
NITROALKENE
56
206
BICYCLIC
A-AMINO
ACID
CORE
OF
TELAPREVIR
214
5-(TRIFLUOROMETHYL)-2-ISOXAZOLINES
AS
ANTIPEST
AGENTS
223
SUMMARY
AND
CONCLUSIONS
230
REFERENCES
231
7
BIOCATALYTIC
SYNTHESIS
OF
CHIRAL
AMINES
USING
OXIDOREDUCTASES
243
SEBASTIAN
C.
COSGROVE,
JEREMY
/.
RAMSDEN,
JUAN
MANGAS-SANCHEZ
AND
NICHOLAS
J,
TURNER
7.1
7.2
7.2.1
7.2.2
7.2.2.1
7.2.2.2
7.2.2.3
7.2.2.4
INTRODUCTION
243
AMINE
OXIDASES
243
INTRODUCTION
243
(S)-SELECTIVE
AMINE
OXIDASES
244
MONOAMINE
OXIDASE
FROM
ASPERGILLUS
NIGER
244
DIRECTED
EVOLUTION
OF
MAO-N
244
SYNTHETIC
APPLICATIONS
AND
CASCADES
247
MONOAMINE
OXIDASE
FROM
PSEUDOMONAS
MONTEILII
ZMU-T01
249
VIII
|
CONTENTS
7.2.2.5
CYCLOHEXYLAMINE
OXIDASE
FROM
BREVIBACTERIUM
OXYDANS
(CHAO)
249
7.2.3
(R)-SELECTIVE
AMINE
OXIDASES
252
7.2.3.1
D-AMINO
ACID
OXIDASE
(PKDAO)
252
7.2.3.2
6-HYDROXY-D-NICOTINE
OXIDASE
(6-HDNO)
FROM
ARTHROBACTER
NICOTINOVORANS
252
7.3
AMINE
DEHYDROGENASES
252
7.3.1
INTRODUCTION
252
7.3.2
DISCOVERY
AND
ENGINEERING
OF
AMDH
253
7.3.2.1
LEUCINE
DEHYDROGENASE
253
7.3.2.2
PHENYLALANINE
DEHYDROGENASE
AND
CHIMERIC
AMINE
DEHYDROGENASE
254
7.3.2.3
NATIVE
AMINE
DEHYDROGENASE
254
7.3.3
SYNTHETIC
APPLICATIONS
OF
AMDH
256
7.3.3.1
PRIMARY
AMINE
SYNTHESIS
WITH
ENGINEERED
AMDH
256
7.3.3.2
PRIMARY
AMINE
SYNTHESIS
WITH
NATURAL
AMDH
258
7.3.3.3
SUBSTRATE
PROMISCUITY
IN
AMDH
259
7.3.3
A
CASCADE
REACTIONS
THAT
USE
AMDH
260
7.4
IMINE
REDUCTASES
262
7.4.1
FROM
BIOSYNTHESIS
TO
BIOCATALYSIS
262
7A.2
BIOCATALYTIC
APPLICATION
OF
IMINE
REDUCTASES
264
7.4.2.1
IREDS
IN
CASCADE
AND
CHEMOENZYMATIC
SYNTHESIS
265
7.4.3
IRED
ENGINEERING
267
7.4.4
IMINE
REDUCTASES
CATALYZING
REDUCTIVE
AMINATION
267
7.4.5
IMINE
REDUCTASE-CATALYZED
AMINE
ALKYLATION
CASCADES
270
7.4.6
ENGINEERING
OF
REDUCTIVE
AMINASES
270
7.5
ENGINEERED
CYTOCHROME
P450S
270
7.6
CONCLUSIONS
AND
PERSPECTIVES
274
REFERENCES
274
8
ENGINEERING
FUNCTIONAL
NANOMATERIALS
THROUGH
THE
AMINO
GROUP
285
GIACOMO
FILIPPINI,
PAOLO
PENGO,
SUSANNA
BOSI,
GIULIO
RAGAZZON,
LUCIA
PASQUATO
AND
MAURIZIO
PRATO
8.1
ABBREVIATIONS
285
8.1
INTRODUCTION
287
8.2
QUANTIFICATION
OF
NANOMATERIAL-BOUND
AMINO
GROUPS
288
8.3
EXPLOITING
AMINO
COMPOUNDS
FOR
THE
FUNCTIONALIZATION
OF
CARBON-BASED
NANOMATERIALS
290
8.3.1
HISTORICAL
BACKGROUNDS:
ALLOTROPES
OF
CARBON
290
8.3.2
USE
OF
AMINES
FOR
THE
FUNCTIONALIZATION
OF
CARBON
NANOSTRUCTURES
290
8.3.3
OTHER
FUNCTIONALIZATION
PROCEDURES
OF
COMMON
CARBON
NANOSTRUCTURES
297
8.3.4
EXFOLIATION
OF
GRAPHITE
WITH
MELAMINE
299
8.3.5
OTHER
CARBON
NANOMATERIALS
301
8.3.5.1
CARBON
NANOHORNS
301
8.3.5.2
CARBON
NANODIAMONDS
305
8.3.5.3
CARBON
NANO-ONIONS
307
CONTENTS
IX
8.3.6
AMINO-FUNCTIONALIZED
CARBON-BASED
NANOMATERIALS
FOR
ANALYTICAL
APPLICATIONS
308
8.4
AMINES
IN
THE
SYNTHESIS
AND
FUNCTIONALIZATION
OF
CARBON
DOTS
309
8.4.1
AMINES
AS
CD
CONSTITUENTS
310
8.4.2
AMINE-RICH
CDS
FROM
ARGININE
AND
ETHYLENEDIAMINE
(NCDS)
312
8.4.2.1
ONE-POT
FUNCTIONALIZATION
OF
NCDS
312
8.4.2.2
POSTFUNCTIONALIZATION
OF
NCDS
313
8.4.2.3
USE
OF
CD-SUPPORTED
AMINES
IN
ORGANOCATALYSIS
315
8.5
AMINES
FOR
THE
ENGINEERING
OF
HYBRID
ORGANIC-INORGANIC
NANOMATERIALS
316
8.5.1
AMINES
AS
HEAD
GROUPS
OR
END
GROUPS
ON
SELF-ASSEMBLED
MONOLAYERS
ON
FLAT
SURFACES
316
8.5.2
ALKYLAMINES
IN
THE
PREPARATION
OF
SEMICONDUCTOR
QUANTUM
DOTS
319
8.5.2.1
SULFUR-AMINE
AND
SELENIUM-AMINE
SYSTEMS
319
8.5.2.2
CAPPING
LIGANDS
FOR
QUANTUM
DOTS
AND
LIGAND
EXCHANGE
BY
AMINES
321
8.5.3
ALKYLAMINES
AS
REAGENTS
FOR
THE
SYNTHESIS
AND
PASSIVATION
OF
METAL
NANOPARTICLES
322
8.5.3.1
ALKYLAMINES
AS
CAPPING
AGENTS
FOR
METAL
NANOPARTICLES
322
8.5.3.2
DISPLACEMENT
OF
AMINES
FROM
THE
SURFACE
OF
METAL
NANOPARTICLES
325
8.5.4
AMINES
ON
THE
OUTER
SURFACE
OF
ORGANIC-INORGANIC
HYBRID
NANOPARTICLES
325
8.5.5
POSTFUNCTIONALIZATION
OF
AMINE-TERMINATED
ORGANIC-INORGANIC
HYBRID
NANOPARTICLES
328
REFERENCES
329
9
RECENT
ADVANCES
IN
THE
SYNTHESIS
OF
NITROGEN
COMPOUNDS
FROM
BIOMASS
DERIVATIVES
341
ANA
C.
FERNANDES
9.1
INTRODUCTION
341
9.2
SYNTHESIS
OF
NITROGEN
COMPOUNDS
FROM
CHITIN
AND
ITS
DERIVATIVES
341
9.3
SYNTHESIS
OF
AMINES
AND
FORMAMIDES
FROM
A-AMINO
ACIDS
345
9.4
SYNTHESIS
OF
NITROGEN
COMPOUNDS
FROM
CELLULOSIC
BIOMASS
DERIVATIVES
348
9.5
SYNTHESIS
OF
NITROGEN
COMPOUNDS
FROM
LIGNIN
DERIVATIVES
366
9.6
SYNTHESIS
OF
NITROGEN
COMPOUNDS
FROM
TRIGLYCERIDES
AND
FATTY
ALCOHOLS
370
9.7
CONCLUSION
373
REFERENCES
373
10
RECENT
ADVANCES
IN
THE
SYNTHESIS
OF
ARYLAMINES
IN
THE
LIGHT
OF
APPLICATION
IN
PHARMACEUTICAL
AND
CHEMICAL
INDUSTRY
377
DINO
BERTHOLD,
ALEXANDER
M.
HAYDL,
JOYCE
C.
LEUNG,
ULRICH
SCHOLZ,
QING
XIAO
AND
ZHIBIN
ZHU
10.1
MODERN
APPROACHES
TO
TRANSITION-METAL-CATALYZED
C-N
COUPLING
IN
INDUSTRY
377
10.1.1
INTRODUCTION
377
10.1.2
TRANSITION-METAL-CATALYZED
C
*N-BOND
FORMATION
377
10.1.2.1
ULLMANN-IYPE
AMINATION
378
10.1.2.2
BUCHWALD-HARTWIG
AMINATION
383
CONTENTS
10.2
NEW
METHODOLOGIES
IN
THE
SYNTHESIS
OF
ARYLAMINES
ON
THE
BRINK
OF
INDUSTRIAL
APPLICATION
388
10.2.1
INTRODUCTION
388
10.2.2
CATALYTIC
C-H
AMINATION
389
10.2.2.1
CATALYTIC
C-H
AMINATION
UNDER
STANDARD
CONDITIONS
389
10.2.2.2
PHOTOREDOX
CATALYSIS
399
10.2.2.3
ELECTROCHEMICAL
APPROACHES
402
10.2.3
DECARBOXYLATIVE
ARYL
AMINATION
405
10.2.4
NICKEL-CATALYZED
C-N
COUPLING
407
10.2.5
OTHER
METAL-CATALYZED
CROSS-COUPLINGS
414
10.2.6
REDUCTIVE
AMINATION
417
10.2.7
HYDROAMINATION
419
10.2.8
SUMMARY
AND
CONCLUSIONS
424
10.3
ADVANCES
TO
ARYLAMINE
FORMATION
USING
INTENSIFIED
AND
MORE
SUSTAINABLE
PROCESS
TECHNOLOGIES
424
10.3.1
INTRODUCTION
424
10.3.2
FLOW
CHEMISTRY
425
10.3.2.1
PD-CATALYZED
C
*
N
BOND
FORMING
REACTION
425
10.3.2.2
NUCLEOPHILIC
AROMATIC
SUBSTITUTION
426
10.3.2.3
TELESCOPED
SEQUENCE
OF
NITRATION
AND
HYDROGENATION
IN
FLOW
SYNTHESIS
428
10.3.2.4
CHAN-LAM
COUPLING
428
10.3.3
IMMOBILIZATION
OF
CATALYSTS/SUPPORTED
CATALYSTS
429
10.3.4
PERSONAL
ACCOUNTS
FROM
CONTRACT MANUFACTURING
COMPANIES
ON
UTILITY
OF
MODERN
FLOW
AMINATION
METHODS
431
10.4
MISCELLANEOUS
ASPECTS
OF
AROMATIC
AMINATION
REACTIONS
IN
THE
WORLD
OF
ACTIVE
PHARMACEUTICAL
INGREDIENTS
431
10.4.1
COHORT
OF
CONCERNS
AND
ITS
REGULATORY
IMPACT
ON
AMINE-BASED
ACTIVE
PHARMACEUTICAL
COMPOUNDS
431
10.4.2
ROLE
OF
CONTROL
OF
ELEMENTAL
IMPURITIES
IN
HUMAN
PHARMA
APPLICATIONS
432
10.4.3
TRANSITION
METAL
ACCOUNTING
433
10.4.4
RECYCLING
OF
METALS,
LIGANDS,
AND
OTHER
COST
DRIVERS
OF
AROMATIC
AMINATION
434
10.4.5
REGULATORY
REQUIREMENTS
FOR
THE
SUBMISSION
OF
A
CATALYTIC
REACTION
IN A
NEW
DRUG
APPLICATION
434
REFERENCES
435
INDEX
445 |
| any_adam_object | 1 |
| any_adam_object_boolean | 1 |
| author2 | Ricci, Alfredo Bernardi, Luca |
| author2_role | edt edt |
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| author_GND | (DE-588)1233695614 |
| author_facet | Ricci, Alfredo Bernardi, Luca |
| building | Verbundindex |
| bvnumber | BV046885758 |
| classification_rvk | VK 7400 |
| ctrlnum | (OCoLC)1249683666 (DE-599)DNB1211570495 |
| 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.BV046885758 |
| illustrated | Illustrated |
| index_date | 2024-07-03T15:19:29Z |
| indexdate | 2024-07-10T08:56:33Z |
| institution | BVB |
| institution_GND | (DE-588)16179388-5 |
| isbn | 9783527347391 |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-032295674 |
| oclc_num | 1249683666 |
| open_access_boolean | |
| owner | DE-11 DE-19 DE-BY-UBM |
| owner_facet | DE-11 DE-19 DE-BY-UBM |
| physical | xiii, 460 Seiten Illustrationen (teilweise farbig) |
| publishDate | 2021 |
| publishDateSearch | 2021 |
| publishDateSort | 2021 |
| publisher | Wiley-VCH |
| record_format | marc |
| spelling | Methodologies in amine synthesis challenges and applications edited by Alfredo Ricci and Luca Bernadi Weinheim Wiley-VCH [2021] © 2021 xiii, 460 Seiten Illustrationen (teilweise farbig) txt rdacontent n rdamedia nc rdacarrier Literaturangaben Amine (DE-588)4001705-9 gnd rswk-swf Chemische Synthese (DE-588)4133806-6 gnd rswk-swf Amine Catalysis Chemie Chemistry Industrial Chemistry Katalyse Materials Science Materialwissenschaften Organic Chemistry Organische Chemie Technische u. Industrielle Chemie CH30: Technische u. Industrielle Chemie CH40: Katalyse CH80: Organische Chemie MS00: Allg. Materialwissenschaften (DE-588)4143413-4 Aufsatzsammlung gnd-content Amine (DE-588)4001705-9 s Chemische Synthese (DE-588)4133806-6 s DE-604 Ricci, Alfredo (DE-588)1233695614 edt Bernardi, Luca edt Wiley-VCH (DE-588)16179388-5 pbl Erscheint auch als Online-Ausgabe, PDF 978-3-527-82617-9 Erscheint auch als Online-Ausgabe, EPUB 978-3-527-82619-3 Erscheint auch als Online-Ausgabe, oBook 978-3-527-82618-6 X:MVB http://www.wiley-vch.de/publish/dt/books/ISBN978-3-527-34739-1/ Kurzbeschreibung DNB Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=032295674&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Methodologies in amine synthesis challenges and applications Amine (DE-588)4001705-9 gnd Chemische Synthese (DE-588)4133806-6 gnd |
| subject_GND | (DE-588)4001705-9 (DE-588)4133806-6 (DE-588)4143413-4 |
| title | Methodologies in amine synthesis challenges and applications |
| title_auth | Methodologies in amine synthesis challenges and applications |
| title_exact_search | Methodologies in amine synthesis challenges and applications |
| title_exact_search_txtP | Methodologies in amine synthesis challenges and applications |
| title_full | Methodologies in amine synthesis challenges and applications edited by Alfredo Ricci and Luca Bernadi |
| title_fullStr | Methodologies in amine synthesis challenges and applications edited by Alfredo Ricci and Luca Bernadi |
| title_full_unstemmed | Methodologies in amine synthesis challenges and applications edited by Alfredo Ricci and Luca Bernadi |
| title_short | Methodologies in amine synthesis |
| title_sort | methodologies in amine synthesis challenges and applications |
| title_sub | challenges and applications |
| topic | Amine (DE-588)4001705-9 gnd Chemische Synthese (DE-588)4133806-6 gnd |
| topic_facet | Amine Chemische Synthese Aufsatzsammlung |
| url | http://www.wiley-vch.de/publish/dt/books/ISBN978-3-527-34739-1/ http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=032295674&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
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