Amide bond activation: concepts and reactions
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| Sprache: | English |
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[2023]
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| Online-Zugang: | Kurzbeschreibung Inhaltsverzeichnis Inhaltsverzeichnis |
| Beschreibung: | xvi, 503 Seiten Illustrationen, Diagramme |
| ISBN: | 9783527348312 352734831X |
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MARC
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| 245 | 1 | 0 | |a Amide bond activation |b concepts and reactions |c edited by Michal Szostak |
| 264 | 1 | |a Weinheim |b Wiley-VCH |c [2023] | |
| 264 | 4 | |c ©2023 | |
| 300 | |a xvi, 503 Seiten |b Illustrationen, Diagramme | ||
| 336 | |b txt |2 rdacontent | ||
| 337 | |b n |2 rdamedia | ||
| 338 | |b nc |2 rdacarrier | ||
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| 650 | 0 | 7 | |a Amide |0 (DE-588)4279702-0 |2 gnd |9 rswk-swf |
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| 650 | 0 | 7 | |a Aktivierung |g Chemie |0 (DE-588)4141761-6 |2 gnd |9 rswk-swf |
| 653 | |a Chemie | ||
| 653 | |a Chemistry | ||
| 653 | |a Computational Chemistry & Molecular Modeling | ||
| 653 | |a Computational Chemistry u. Molecular Modeling | ||
| 653 | |a Organic Chemistry | ||
| 653 | |a Organische Chemie | ||
| 653 | |a Pharmaceutical & Medicinal Chemistry | ||
| 653 | |a Pharmazeutische u. Medizinische Chemie | ||
| 653 | |a CH60: Pharmazeutische u. Medizinische Chemie | ||
| 653 | |a CH80: Organische Chemie | ||
| 653 | |a CHD0: Computational Chemistry u. Molecular Modeling | ||
| 653 | |a Technische u. Industrielle Chemie | ||
| 653 | |a Amidbindung | ||
| 653 | |a Industrial Chemistry | ||
| 653 | |a CH30: Technische u. Industrielle Chemie | ||
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| 689 | 0 | |5 DE-604 | |
| 700 | 1 | |a Szostak, Michal |0 (DE-588)1190908603 |4 edt | |
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Datensatz im Suchindex
| _version_ | 1804184964095279104 |
|---|---|
| adam_text | CONTENTS
PREFACE
XV
1
BRIDGED
LACTAMS
AS
MODEL
SYSTEMS
FOR
AMIDIC
DISTORTION
1
TYLER
J.
FULTON,
YUN
E.
DU,
AND
BRIAN
M.
STOLTZ
1.1
1.2
1.2.1
1.2.2
INTRODUCTION
AND
SCOPE
1
GENERAL
PROPERTIES
OF
BRIDGED
LACTAMS
3
PARAMETERS
OF
AMIDE
BOND
DISTORTION
3
BOND
LENGTHS,
BOND
ANGLES,
AND
SPECTROSCOPIC
PROPERTIES
OF
BRIDGED
LACTAMS
5
1.2.3
N
VS.
O-PROTONATION
AND
METHYLATION
AND
STRUCTURAL
EFFECTS
OF
N-COORDINATION
7
1.2.4
1.3
1.3.1
1.3.1.1
1.3.1.2
1.3.2
1.3.2.1
1.3.2.2
1.3.2.3
1.3.2.4
1.3.2.5
1.3.3
1.3.4
1.3.4.1
1.4
TWISTED
AMIDE
BASICITY
AND
PK,
MEASUREMENTS
14
REACTIVITY
OF
BRIDGED
LACTAMS
15
REACTIVITY
OF
THE
LACTAM
NITROGEN
15
HYDROLYSIS
OF
THE
N-C(O)
BOND
15
CLEAVAGE
OF
THE
O
C-N
BOND
17
REACTIVITY
OF
THE
CARBONYL
GROUP
18
HETEROATOM
NUCLEOPHILES
18
ORGANOME
TALLIES
19
REDUCTION
OF
THE
CARBONYL
20
OLEFINATION
AND
EPOXIDATION
REACTIONS
20
ENOLATE
AND
CONJUGATE
ADDITION
CHEMISTRY
21
POLYMERIZATION
REACTIONS
22
MISCELLANEOUS
REACTIONS
23
RING
OPENING
VIA
OLEFIN
METATHESIS
23
CONCLUSIONS
AND
OUTLOOK
24
REFERENCES
24
VI
CONTENTS
2
MODIFICATION
OF
AMIDIC
RESONANCE
THROUGH
HETEROATOM
SUBSTITUTION
AT
NITROGEN:
ANOMERIC
AMIDES
29
STEPHEN
A,
GLOVER
AND
ADAM
A.
ROSSER
2.1
2.2
2.2.1
2.2.2
2.2.3
2.2.4
2.2.5
INTRODUCTION
29
PROPERTIES
OF
ANOMERIC
AMIDES
32
STRUCTURAL
PROPERTIES
32
NATURAL
BOND
ORDER
ANALYSIS
33
THEORETICAL
DETERMINATION
OF
AMIDE
BOND
RESONANCE
35
SOURCES
OF
ANOMERIC
AMIDES
37
EXPERIMENTAL
EVIDENCE
FOR
REDUCED
RESONANCE
IN
ANOMERIC
AMIDES
38
2.2.6
2.2.7
SPECTROSCOPIC
PROPERTIES
OF
ANOMERIC
AMIDES
43
THEORETICAL
STRUCTURES
AND
AMIDICITIES
OF
MODEL
ANOMERIC
AMIDES
46
2.3
2.3.1
2.3.2
2.3.2.1
2.3.2.2
2.3.3
2.3.3.1
2.3.3.2
2.3.3.3
REACTIVITY
OF
ANOMERIC
AMIDES
50
THE
ANOMERIC
EFFECT
50
REACTIVITY
AT
THE
ANOMERIC
AMIDE
NITROGEN
53
S
N
2
REACTIONS
53
ELIMINATION
REACTIONS
(S
N
1-TYPE
PROCESSES)
56
AMIDE
BOND
SCISSION
REACTIONS:
THE
HERON
REACTION
57
HERON
REACTIONS
OF
N-ALKOXY-N-AMINOAMIDES
58
OTHER
HERON
REACTIONS
60
THE
ROLE
OF
THE
NY-O*NX
ANOMERIC
EFFECT
AND
RESONANCE
IN
HERON
REACTIONS
63
2.4
CONCLUDING
REMARKS
66
REFERENCES
68
3
AMIDE
BOND
ACTIVATION
BY
TWISTING
AND
NITROGEN
PYRAMIDALIZATION
79
YUKO
OTANI
AND
TOMOHIKO
OHWADA
3.1
3.2
INTRODUCTION
79
NONPLANAR
AMIDES
THAT
ARE
SUFFICIENTLY
STABLE
FOR
CHEMICAL
MODIFICATION
80
3.2.1
3.2.2
3.2.3
3.3
NONPLANAR
AMIDES
80
THIOAMIDES
83
CHEMICAL
STABILITY
OF
NITROGEN
PYRAMIDAL
AMIDES
83
APPLICATION
TO
AMINO
ACIDS:
ARTIFICIAL
HELICES
COMPOSED
OF
BICYCLIC
AMINO
ACIDS
85
3.3.1
3.3.2
3.3.3
3.3.3.1
3.4
CONFORMATIONAL
PREFERENCE
OF
BICYCLIC
P
AMINO
ACIDS
85
BRIDGEHEAD-SUBSTITUTED
BICYCLIC
AMINO
ACIDS
88
APPLICATION
TO
ARTIFICIAL
HELICES
AND
STRAND
MIMICS
90
HETEROOLIGOMERS
90
APPLICATIONS
OF
HELICAL
PEPTIDES
AS
INHIBITORS
OF
P53-MDM2/MDMX
INTERACTION
92
CONTENTS
VII
3.5
NONPLANAR
LACTAM
AMIDE
SPINNING
93
3.5.1
LACTAM
AMIDE
ROTATION
94
3.6
CONCLUSION
AND
PROSPECTS
95
REFERENCES
96
4
TRANSITION-METAL-FREE
REACTIONS
OF
AMIDES
BY
TETRAHEDRAL
INTERMEDIATES
101
MARCO
BLANGETTI,
KAREN
DE
LA
VEGA-HERNANDEZ,
MARGHERITA
MIELE,
AND
VITTORIO
PACE
4.1
INTRODUCTION
101
4.2
SYNTHESIS
OF
CARBONYLS
FROM
AMIDES
102
4.2.1
ADDITION
TO
CANONICAL
AMIDES
102
4.2.2
VARIATION
OF
THE
AMIDE
STRUCTURE
107
4.2.3
ISOLATION
OF
TETRAHEDRAL
INTERMEDIATES
115
4.3
RECENT
USES
OF
AMIDES
AND
/V-ALKOXYAMIDES
FOR
THE
SYNTHESIS
OF
AMINES
119
4.4
ELECTROPHILIC
AMIDE
LINKAGE
ACTIVATION
128
4.4.1
GENERAL
CONCEPT
128
4.4.2
SYNTHESIS
OF
CARBONYL-LIKE
COMPOUNDS
129
4.4.3
SYNTHESIS
OF
AMINE-LIKE
COMPOUNDS
137
4.4.4
ACTIVATION
OF
AMIDES
WITH
DIFFERENT
ELECTROPHILIC
AGENTS
144
4.5
SYNTHESIS
OF
HETEROCYCLES
145
4.6
CONCLUSIONS
AND
OUTLOOK
150
REFERENCES
150
5
ELECTROPHILIC
AMIDE
BOND
FUNCTIONALIZATION
157
CARLOS
R.
GONSALVES
AND
DANIEL
KAISER
5.1
INTRODUCTION:
ELECTROPHILIC
ACTIVATION
157
5.2
INTRODUCTION:
ELECTROPHILIC
ACTIVATION
OF
AMIDES
158
5.3
EARLY
ENDEAVORS
IN
ELECTROPHILIC
AMIDE
ACTIVATION
159
5.3.1
HISTORY
OF
THE
ACTIVATION
OF
SECONDARY
AMIDES
159
5.3.2
HISTORY
OF
THE
ACTIVATION
OF
TERTIARY
AMIDES
160
5.4
AMIDE
BOND
FUNCTIONALIZATION
OF
ACTIVATED
TERTIARY
AMIDES
164
5.4.1
[2+2]-CYCLOADDITIONS
164
5.4.2
STEREOSELECTIVE
CYCLOADDITIONS
167
5.4.3
NUCLEOPHILE
ADDITION
168
5.4.3.1
CARBON
NUCLEOPHILES
168
5.4.3.2
HYDRIDIC
REDUCTION
170
5.4.3.3
HETEROATOM
NUCLEOPHILES
171
5.5
AMIDE
BOND
FUNCTIONALIZATION
OF
ACTIVATED
SECONDARY
AMIDES
175
5.5.1
SYNTHESIS
AND
FUNCTIONALIZATION
OF
HETEROCYCLES
176
5.5.2
KETONE
SYNTHESIS
179
5.6
CONCLUSIONS
180
REFERENCES
181
VIII
CONTENTS
6
TRANSAMIDATION
OF
CARBOXAMIDES
AND
AMIDE
DERIVATIVES:
MECHANISTIC
INSIGHTS,
CONCEPTS,
AND
REACTIONS
187
PAOLA
ACOSTA-GUZMAN,
JOHN
CORREDOR-BARINAS,
AND
DIEGO
GAMBA-SANCHEZ
6.1
6.2
6.3
6.3.1
6.3.2
6.3.3
6.3.4
6.3.4.1
6.3.4.2
6.3.4.3
6.3.4.4
6.3.5
6.4
INTRODUCTION
187
HISTORICAL
BACKGROUND
188
DIRECT
TRANSAMIDATION
OF
CARBOXAMIDES
190
MECHANISTIC
INSIGHTS
190
TRANSITION
METAL
CATALYSIS
193
ORGANOCATALYSIS
195
OTHER
CATALYTIC
AND
PROMOTED
PROCESSES
198
BASES
198
BORON
DERIVATIVES
199
HETEROGENEOUS
CATALYSIS
200
OTHER
PROMOTERS
201
CATALYST
AND
PROMOTER-FREE
PROCESSES
203
TRANSAMIDATION
BY
THE
PREVIOUS
FUNCTIONALIZATION
OF
THE
AMIDE
BOND
204
6.4.1
6.4.2
TRANSAMIDATION
OF
ACTIVATED
SUBSTRATES
USING
METALLIC
CATALYSTS
205
TRANSAMIDATION
OF
ACTIVATED
SUBSTRATES
USING
FLUORIDE
AS
AN
AUXILIARY
207
6.4.3
6.4.4
TRANSAMIDATION
OF
ACTIVATED
SUBSTRATES
USING
OTHER
PROMOTERS
208
TRANSAMIDATION
OF
ACTIVATED
SUBSTRATES
WITHOUT
PROMOTERS
OR
CATALYSTS
209
6.5
6.5.1
6.5.2
6.5.3
6.5.4
6.6
TRANSAMIDATION
WITH
ATYPICAL
SUBSTRATES
211
REDUCTIVE
TRANSAMIDATION
211
OXIDATIVE
TRANSAMIDATION
212
USING
CARBONYL
AND
THIOCARBONYL
HETEROCYCLES
AS
ACTIVATORS
213
FROM
AMIDINES
214
CONCLUSIONS
AND
PERSPECTIVES
215
REFERENCES
216
7
AMIDE
BOND
ESTERIFICATION
AND
HYDROLYSIS
221
KAZUSHI
MASHIMA,
TAKAHIRO
HIROI,
AND
HARUKI
NAGAE
7.1
7.2
7.3
7.4
7.5
STOICHIOMETRIC
REACTIONS
221
CATALYTIC
REACTIONS
228
N-P-HYDROXYETHYL
AMIDES
232
CHELATING
AUXILIARY
AT
THE
NITROGEN
ATOM
OF
AMIDES
234
ACTIVATED
AMIDES
235
REFERENCES
237
CONTENTS
IX
8
ACTIVATION
OF
AMIDE
C-N
BONDS
BY
NICKEL
CATALYSIS
243
LIANA
HIE
AND
TEJAS
K.
SHAH
8.1
8.2
8.3
8.4
8.5
8.6
8.7
8.8
INTRODUCTION
243
ESTERIFICATION
OF
AMIDES
243
HYDROLYSIS
OF
AMIDES
248
TRANSAMIDATION
249
SUZUKI-MIYAURA
COUPLING
OF
AMIDES
255
NEGISHI
COUPLING
OF
AMIDES
258
MIZOROKI-HECK
COUPLING
OF
AMIDES
261
REDUCTION
AND
REDUCTIVE
COUPLING
OF
AMIDES
265
REFERENCES
269
9
PD-NHC
CATALYSIS
IN
CROSS-COUPLING
OF
AMIDES
273
FAEZ
S.
ALOTAIBI,
MICHAEL
R.
CHHOUN,
AND
GREGORY
R.
COOK
9.1
9.2
9.3
INTRODUCTION
273
PD(II)-NHC-CATALYZED
CROSS-COUPLING
REACTIONS
OF
AMIDES
274
PD(NHC)(ALLYL)CL
PRECATALYST
IN
SUZUKI-MIYAURA
CROSS-COUPLING
OF
AMIDES
275
9.4
PD(N3-1-T-BU-INDENYL)(IPR)CL-CATALYZED
SUZUKI-MIYAURA
CROSS-COUPLING
OF
AMIDES
279
9.5
PD-PEPPSSI
PRECATALYST
IN
THE
SUZUKI-MIYAURA
CROSS-COUPLING
OF
AMIDES
281
9.6
VARIOUS
PD-NHC
PRECATALYSTS
SUITABLE
FOR
CROSS-COUPLING
OF
AMIDES
286
9.7
CONCLUSION
288
REFERENCES
288
10
CROSS-COUPLING
OF
AMIDES
THROUGH
DECARBONYLATION
293
HONG
LU
AND
HAO
WEI
10.1
10.2
10.2.1
10.2.2
10.3
10.3.1
10.3.2
10.3.3
10.4
INTRODUCTION
293
DECARBONYLATION
OF
CYCLIC
AMIDE
DERIVATIVES
294
PHTHALIMIDES
295
SACCHARINS
AND
OTHER
CYCLIC
AMIDE
DERIVATIVES
297
DECARBONYLATION
OF
ACYCLIC
AMIDE
DERIVATIVES
298
N-ACYL-GLUTARIMIDES
298
N-ACYLSACCHARIN
AMIDES
302
OTHER
ACYCLIC
AMIDES
302
CONCLUSION
305
REFERENCES
305
CONTENTS
11
TRANSITION
METAL-CATALYZED
RADICAL
REACTIONS
OF
AMIDES
307
TALINE
KERACKIAN,
DIDIER
BOUYSSI,
NUNO
MONTEIRO,
AND
ABDERRAHMANE
AMGOUNE
11.1
11.2
INTRODUCTION
307
REACTIONS
INVOLVING
AMIDES
AS
PRECURSORS
TO
ORGANOMETALLIC
COMPOUNDS
308
11.2.1
RADICAL
REACTIONS
OF
AMIDES
VIA
METAL-CATALYZED
C-N
BOND
ACTIVATION
308
11.2.1.1
11.2.1.2
11.2.2
11.2.2.1
11.2.2.2
11.3
REDUCTIVE
CROSS-ELECTROPHILE
CROSS-COUPLING
REACTIONS
309
PHOTOREDOX
CROSS-COUPLING
REACTIONS
312
CHELATION-ASSISTED
RADICAL
REACTIONS
OF
AMIDES
316
AMIDE-DIRECTED
C-H
BOND
FUNCTIONALIZATION
316
AMIDE-DIRECTED
FUNCTIONALIZATION
OF
UNACTIVATED
ALKENES
318
REACTIONS
INVOLVING
AMIDES
AS
PRECURSORS
TO
NITROGEN
OR
CARBON-CENTERED
RADICALS
323
11.3.1
11.3.1.1
11.3.1.2
11.3.2
11.3.2.1
REACTIONS
OF
AMIDES
VIA
AMIDYL
RADICALS
323
VICINAL
DIFUNCTIONALIZATION
OF
PENDANT
OLEFINS
324
DISTANT
C-H
BOND
FUNCTIONALIZATION
325
REACTIONS
OF
AMIDES
VIA
A-AMINOALKYL
RADICALS
328
C-H
BOND
FUNCTIONALIZATION
VIA
RADICAL
ADDITION
TO
ALKENES
328
11.3.2.2
11.3.3
11.4
C-H
BOND
FUNCTIONALIZATION
VIA
CROSS-COUPLING
329
REACTIONS
OF
AMIDES
VIA
CARBAMOYL
RADICALS
331
CONCLUSION
333
REFERENCES
334
12
WEINREB
AMIDE
AS
A
MULTIFACETED
DIRECTING
GROUP
IN
C-H
ACTIVATION
339
JAYABRATA
DAS
AND
DEBABRATA
MAITI
12.1
12.2
12.2.1
12.2.2
12.2.3
12.2.4
12.2.5
12.3
12.4
INTRODUCTION
339
WEINREB
AMIDE-DIRECTED
C(SP
2
)-H
ACTIVATION
340
RU-CATALYZED
REACTIONS
340
CO-CATALYZED
REACTIONS
344
PD-CATALYZED
REACTIONS
346
RH-CATALYZED
REACTIONS
352
IR-CATALYZED
REACTIONS
354
WEINREB
AMIDE-DIRECTED
C(SP
3
)-H
ACTIVATION
359
CONCLUSIONS
AND
OUTLOOK
362
REFERENCES
362
CONTENTS
|
XI
13
COMPUTATIONAL
STUDIES
OF
AMIDE
C-N
BOND
ACTIVATION
365
XIN
HONG,
PEI-PEI
XIE,
ZHI-XIN
QIN,
AND
SHUO-QING
ZHANG
13.1
INTRODUCTION
365
13.2
GENERAL
MECHANISMS
OF
AMIDE
C-N
BOND
CLEAVAGE
AND
DERIVATIZATION
367
13.3
COMPUTATIONAL
STUDIES
ON
THE
MECHANISM
AND
SELECTIVITY
OF
LEWIS
ACID-MEDIATED
NUCLEOPHILIC
SUBSTITUTION
OF
AMIDES
368
13.3.1
COMPUTATIONAL
STUDIES
ON
THE
MECHANISM
AND
SELECTIVITY
OF
LIHMDS-MEDIATED
TRANSAMIDATION
369
13.3.2
COMPUTATIONAL
STUDIES
ON
THE
MECHANISM
AND
REACTIVITY
OF
ZN
CATALYZED
ESTERIFICATION
OF
AMIDES
373
13.3.3
COMPUTATIONAL
STUDIES
ON
THE
MECHANISM
OF
AMMONIUM
SALT-MEDIATED
HYDRAZINOLYSIS
OF
AMIDES
375
13.3.4
COMPUTATIONAL
STUDIES
ON
THE
MECHANISM
OF
ORGANOCATALYTIC
ASYMMETRIC
ALCOHOLYSIS
OF
N-SULFONYL
AMIDE
378
13.4
COMPUTATIONAL
STUDIES
ON
THE
MECHANISM
AND
SELECTIVITY
OF
TRANSITION
METAL
CATALYZED
CROSS-COUPLING
OF
AMIDES
380
13.4.1
COMPUTATIONAL
STUDY
ON
THE
MECHANISM
AND
REACTIVITY
OF
NI-CATALYZED
ESTERIFICATION
OF
AMIDES
381
13.4.2
COMPUTATIONAL
STUDY
ON
THE
MECHANISM OF
NI-CATALYZED
SUZUKI-MIYAURA
COUPLING
OF
AMIDES
387
13.4.3
COMPUTATIONAL
STUDY
ON
THE
MECHANISM
AND
SELECTIVITY
OF
NI-CATALYZED
C-N
BOND
ACTIVATION
OF
TWISTED
AMIDES
388
13.4.4
COMPUTATIONAL
STUDY
ON
THE
STRUCTURE-ACTIVITY
RELATIONSHIP
OF
NI-CATALYZED
C-N
BOND
ACTIVATION
OF
AMIDES
391
13.4.5
COMPUTATIONAL
STUDY
ON
THE
MECHANISM
OF
PD-CATALYZED
SUZUKI-MIYAURA
COUPLING
OF
AMIDES
395
13.4.6
COMPUTATIONAL
STUDY
ON
THE
MECHANISM
OF
PD-CATALYZED
TRANSAMIDATION
OF
AMIDES
398
13.5
OUTLOOK
398
REFERENCES
399
14
ESTERS
AS
VIABLE
ACYL
CROSS-COUPLING
ELECTROPHILES
403
OMID
DANESHFAR
AND
STEPHEN
G.
NEWMAN
14.1
INTRODUCTION
403
14.2
EARLY
WORK
IN
THE
CROSS-COUPLING
OF
CARBOXYLIC
ACID
DERIVATIVES
404
14.3
DECARBONYLATIVE
COUPLING
OF
ARYL
ESTERS
408
14.3.1
MIZOROKI-HECK-TYPE
COUPLING
408
14.3.2
C-H
BIARYL
COUPLING
409
XII
CONTENTS
14.3.3
14.3.4
14.3.5
14.3.5.1
14.3.5.2
14.3.5.3
14.3.5.4
14.3.5.5
14.3.6
14.3.6.1
14.3.6.2
14.3.6.3
14.3.6.4
14.4
14.4.1
14.4.2
14.4.3
14.4.4
14.4.5
14.4.6
14.5
14.5.1
14.5.2
14.5.3
14.6
14.6.1
14.6.2
14.6.3
14.7
SUZUKI-MIYAURA
COUPLING
412
SILYLATION
AND
BORYLATION
41
7
OTHER
C-C/C-H
BOND
FORMING
REACTIONS
419
SONOGASHIRA-TYPE
COUPLINGS
419
REDUCTION
421
NEGISHI-TYPE
COUPLING
421
CYANATION
422
METHYLATION
422
OTHER
C-HETEROATOM
BOND
FORMING
REACTIONS
424
ETHERIFICATION
424
AMINATION
424
THIOETHERIFICATION
427
CARBON-PHOSPHORUS
BOND
FORMATION
428
CARBONYL
RETENTIVE
COUPLING
OF
PHENYL
ESTERS
429
SUZUKI-MIYAURA
COUPLING
429
AMIDATION
433
CROSS-ELECTROPHILE
COUPLING
434
ESTER
TRANSFER
AND
ESTER
DANCE
435
DEOXYGENATIVE
ORGANOPHOSPHORUS
COUPLING
437
ALKYNE
INSERTION
438
CARBONYL
RETENTIVE
COUPLING
OF
ALKYL
ESTERS
439
AMIDATION
439
MIZOROKI-HECK-TYPE
DOMINO
REACTIONS
441
SUZUKI-MIYAURA
COUPLING
443
DECARBONYLATIVE
COUPLINGS
OF
ALKYL
ESTERS
444
DIRECTING
GROUP
ASSISTANCE
444
METHYLATION
445
ORGANOSTANNANE
FORMATION
445
CONCLUSION
AND
OUTLOOK
446
REFERENCES
447
15
CROSS-COUPLING
OF
AROMATIC
ESTERS
BY
DECARBONYLATION
453
KEI
MUTO
AND
JUNICHIRO
YAMAGUCHI
15.1
15.2
15.3
15.4
15.5
15.6
15.7
15.8
15.9
15.10
15.11
15.12
INTRODUCTION
453
OVERVIEW
OF
DECARBONYLATIVE
COUPLING
453
DECARBONYLATIVE
MIZOROKI-HECK
REACTION
457
DECARBONYLATIVE
ALKYNE
INSERTIONS
459
SUZUKI-MIYAURA
COUPLING
460
NEGISHI
COUPLING
463
SONOGASHIRA
COUPLING
464
A-ARYLATION
465
CYANATION
465
C-H
ARYLATION
466
C-N
BOND
FORMATIONS
470
C-P
BOND
FORMATION
471
CONTENTS
XIII
15.13
ETHERIFICATION
473
15.14
15.15
15.16
15.17
15.18
THIOETHERIFICATION
473
HYDROGENATION
473
BORYLATION,
SILYLATION,
AND
STANNYLATION
475
MISCELLANEOUS
478
SUMMARY
483
REFERENCES
483
INDEX
487
|
| adam_txt |
CONTENTS
PREFACE
XV
1
BRIDGED
LACTAMS
AS
MODEL
SYSTEMS
FOR
AMIDIC
DISTORTION
1
TYLER
J.
FULTON,
YUN
E.
DU,
AND
BRIAN
M.
STOLTZ
1.1
1.2
1.2.1
1.2.2
INTRODUCTION
AND
SCOPE
1
GENERAL
PROPERTIES
OF
BRIDGED
LACTAMS
3
PARAMETERS
OF
AMIDE
BOND
DISTORTION
3
BOND
LENGTHS,
BOND
ANGLES,
AND
SPECTROSCOPIC
PROPERTIES
OF
BRIDGED
LACTAMS
5
1.2.3
N
VS.
O-PROTONATION
AND
METHYLATION
AND
STRUCTURAL
EFFECTS
OF
N-COORDINATION
7
1.2.4
1.3
1.3.1
1.3.1.1
1.3.1.2
1.3.2
1.3.2.1
1.3.2.2
1.3.2.3
1.3.2.4
1.3.2.5
1.3.3
1.3.4
1.3.4.1
1.4
TWISTED
AMIDE
BASICITY
AND
PK,
MEASUREMENTS
14
REACTIVITY
OF
BRIDGED
LACTAMS
15
REACTIVITY
OF
THE
LACTAM
NITROGEN
15
HYDROLYSIS
OF
THE
N-C(O)
BOND
15
CLEAVAGE
OF
THE
O
C-N
BOND
17
REACTIVITY
OF
THE
CARBONYL
GROUP
18
HETEROATOM
NUCLEOPHILES
18
ORGANOME
TALLIES
19
REDUCTION
OF
THE
CARBONYL
20
OLEFINATION
AND
EPOXIDATION
REACTIONS
20
ENOLATE
AND
CONJUGATE
ADDITION
CHEMISTRY
21
POLYMERIZATION
REACTIONS
22
MISCELLANEOUS
REACTIONS
23
RING
OPENING
VIA
OLEFIN
METATHESIS
23
CONCLUSIONS
AND
OUTLOOK
24
REFERENCES
24
VI
CONTENTS
2
MODIFICATION
OF
AMIDIC
RESONANCE
THROUGH
HETEROATOM
SUBSTITUTION
AT
NITROGEN:
ANOMERIC
AMIDES
29
STEPHEN
A,
GLOVER
AND
ADAM
A.
ROSSER
2.1
2.2
2.2.1
2.2.2
2.2.3
2.2.4
2.2.5
INTRODUCTION
29
PROPERTIES
OF
ANOMERIC
AMIDES
32
STRUCTURAL
PROPERTIES
32
NATURAL
BOND
ORDER
ANALYSIS
33
THEORETICAL
DETERMINATION
OF
AMIDE
BOND
RESONANCE
35
SOURCES
OF
ANOMERIC
AMIDES
37
EXPERIMENTAL
EVIDENCE
FOR
REDUCED
RESONANCE
IN
ANOMERIC
AMIDES
38
2.2.6
2.2.7
SPECTROSCOPIC
PROPERTIES
OF
ANOMERIC
AMIDES
43
THEORETICAL
STRUCTURES
AND
AMIDICITIES
OF
MODEL
ANOMERIC
AMIDES
46
2.3
2.3.1
2.3.2
2.3.2.1
2.3.2.2
2.3.3
2.3.3.1
2.3.3.2
2.3.3.3
REACTIVITY
OF
ANOMERIC
AMIDES
50
THE
ANOMERIC
EFFECT
50
REACTIVITY
AT
THE
ANOMERIC
AMIDE
NITROGEN
53
S
N
2
REACTIONS
53
ELIMINATION
REACTIONS
(S
N
1-TYPE
PROCESSES)
56
AMIDE
BOND
SCISSION
REACTIONS:
THE
HERON
REACTION
57
HERON
REACTIONS
OF
N-ALKOXY-N-AMINOAMIDES
58
OTHER
HERON
REACTIONS
60
THE
ROLE
OF
THE
NY-O*NX
ANOMERIC
EFFECT
AND
RESONANCE
IN
HERON
REACTIONS
63
2.4
CONCLUDING
REMARKS
66
REFERENCES
68
3
AMIDE
BOND
ACTIVATION
BY
TWISTING
AND
NITROGEN
PYRAMIDALIZATION
79
YUKO
OTANI
AND
TOMOHIKO
OHWADA
3.1
3.2
INTRODUCTION
79
NONPLANAR
AMIDES
THAT
ARE
SUFFICIENTLY
STABLE
FOR
CHEMICAL
MODIFICATION
80
3.2.1
3.2.2
3.2.3
3.3
NONPLANAR
AMIDES
80
THIOAMIDES
83
CHEMICAL
STABILITY
OF
NITROGEN
PYRAMIDAL
AMIDES
83
APPLICATION
TO
AMINO
ACIDS:
ARTIFICIAL
HELICES
COMPOSED
OF
BICYCLIC
AMINO
ACIDS
85
3.3.1
3.3.2
3.3.3
3.3.3.1
3.4
CONFORMATIONAL
PREFERENCE
OF
BICYCLIC
P
AMINO
ACIDS
85
BRIDGEHEAD-SUBSTITUTED
BICYCLIC
AMINO
ACIDS
88
APPLICATION
TO
ARTIFICIAL
HELICES
AND
STRAND
MIMICS
90
HETEROOLIGOMERS
90
APPLICATIONS
OF
HELICAL
PEPTIDES
AS
INHIBITORS
OF
P53-MDM2/MDMX
INTERACTION
92
CONTENTS
VII
3.5
NONPLANAR
LACTAM
AMIDE
SPINNING
93
3.5.1
LACTAM
AMIDE
ROTATION
94
3.6
CONCLUSION
AND
PROSPECTS
95
REFERENCES
96
4
TRANSITION-METAL-FREE
REACTIONS
OF
AMIDES
BY
TETRAHEDRAL
INTERMEDIATES
101
MARCO
BLANGETTI,
KAREN
DE
LA
VEGA-HERNANDEZ,
MARGHERITA
MIELE,
AND
VITTORIO
PACE
4.1
INTRODUCTION
101
4.2
SYNTHESIS
OF
CARBONYLS
FROM
AMIDES
102
4.2.1
ADDITION
TO
CANONICAL
AMIDES
102
4.2.2
VARIATION
OF
THE
AMIDE
STRUCTURE
107
4.2.3
ISOLATION
OF
TETRAHEDRAL
INTERMEDIATES
115
4.3
RECENT
USES
OF
AMIDES
AND
/V-ALKOXYAMIDES
FOR
THE
SYNTHESIS
OF
AMINES
119
4.4
ELECTROPHILIC
AMIDE
LINKAGE
ACTIVATION
128
4.4.1
GENERAL
CONCEPT
128
4.4.2
SYNTHESIS
OF
CARBONYL-LIKE
COMPOUNDS
129
4.4.3
SYNTHESIS
OF
AMINE-LIKE
COMPOUNDS
137
4.4.4
ACTIVATION
OF
AMIDES
WITH
DIFFERENT
ELECTROPHILIC
AGENTS
144
4.5
SYNTHESIS
OF
HETEROCYCLES
145
4.6
CONCLUSIONS
AND
OUTLOOK
150
REFERENCES
150
5
ELECTROPHILIC
AMIDE
BOND
FUNCTIONALIZATION
157
CARLOS
R.
GONSALVES
AND
DANIEL
KAISER
5.1
INTRODUCTION:
ELECTROPHILIC
ACTIVATION
157
5.2
INTRODUCTION:
ELECTROPHILIC
ACTIVATION
OF
AMIDES
158
5.3
EARLY
ENDEAVORS
IN
ELECTROPHILIC
AMIDE
ACTIVATION
159
5.3.1
HISTORY
OF
THE
ACTIVATION
OF
SECONDARY
AMIDES
159
5.3.2
HISTORY
OF
THE
ACTIVATION
OF
TERTIARY
AMIDES
160
5.4
AMIDE
BOND
FUNCTIONALIZATION
OF
ACTIVATED
TERTIARY
AMIDES
164
5.4.1
[2+2]-CYCLOADDITIONS
164
5.4.2
STEREOSELECTIVE
CYCLOADDITIONS
167
5.4.3
NUCLEOPHILE
ADDITION
168
5.4.3.1
CARBON
NUCLEOPHILES
168
5.4.3.2
HYDRIDIC
REDUCTION
170
5.4.3.3
HETEROATOM
NUCLEOPHILES
171
5.5
AMIDE
BOND
FUNCTIONALIZATION
OF
ACTIVATED
SECONDARY
AMIDES
175
5.5.1
SYNTHESIS
AND
FUNCTIONALIZATION
OF
HETEROCYCLES
176
5.5.2
KETONE
SYNTHESIS
179
5.6
CONCLUSIONS
180
REFERENCES
181
VIII
CONTENTS
6
TRANSAMIDATION
OF
CARBOXAMIDES
AND
AMIDE
DERIVATIVES:
MECHANISTIC
INSIGHTS,
CONCEPTS,
AND
REACTIONS
187
PAOLA
ACOSTA-GUZMAN,
JOHN
CORREDOR-BARINAS,
AND
DIEGO
GAMBA-SANCHEZ
6.1
6.2
6.3
6.3.1
6.3.2
6.3.3
6.3.4
6.3.4.1
6.3.4.2
6.3.4.3
6.3.4.4
6.3.5
6.4
INTRODUCTION
187
HISTORICAL
BACKGROUND
188
DIRECT
TRANSAMIDATION
OF
CARBOXAMIDES
190
MECHANISTIC
INSIGHTS
190
TRANSITION
METAL
CATALYSIS
193
ORGANOCATALYSIS
195
OTHER
CATALYTIC
AND
PROMOTED
PROCESSES
198
BASES
198
BORON
DERIVATIVES
199
HETEROGENEOUS
CATALYSIS
200
OTHER
PROMOTERS
201
CATALYST
AND
PROMOTER-FREE
PROCESSES
203
TRANSAMIDATION
BY
THE
PREVIOUS
FUNCTIONALIZATION
OF
THE
AMIDE
BOND
204
6.4.1
6.4.2
TRANSAMIDATION
OF
ACTIVATED
SUBSTRATES
USING
METALLIC
CATALYSTS
205
TRANSAMIDATION
OF
ACTIVATED
SUBSTRATES
USING
FLUORIDE
AS
AN
AUXILIARY
207
6.4.3
6.4.4
TRANSAMIDATION
OF
ACTIVATED
SUBSTRATES
USING
OTHER
PROMOTERS
208
TRANSAMIDATION
OF
ACTIVATED
SUBSTRATES
WITHOUT
PROMOTERS
OR
CATALYSTS
209
6.5
6.5.1
6.5.2
6.5.3
6.5.4
6.6
TRANSAMIDATION
WITH
ATYPICAL
SUBSTRATES
211
REDUCTIVE
TRANSAMIDATION
211
OXIDATIVE
TRANSAMIDATION
212
USING
CARBONYL
AND
THIOCARBONYL
HETEROCYCLES
AS
ACTIVATORS
213
FROM
AMIDINES
214
CONCLUSIONS
AND
PERSPECTIVES
215
REFERENCES
216
7
AMIDE
BOND
ESTERIFICATION
AND
HYDROLYSIS
221
KAZUSHI
MASHIMA,
TAKAHIRO
HIROI,
AND
HARUKI
NAGAE
7.1
7.2
7.3
7.4
7.5
STOICHIOMETRIC
REACTIONS
221
CATALYTIC
REACTIONS
228
N-P-HYDROXYETHYL
AMIDES
232
CHELATING
AUXILIARY
AT
THE
NITROGEN
ATOM
OF
AMIDES
234
ACTIVATED
AMIDES
235
REFERENCES
237
CONTENTS
IX
8
ACTIVATION
OF
AMIDE
C-N
BONDS
BY
NICKEL
CATALYSIS
243
LIANA
HIE
AND
TEJAS
K.
SHAH
8.1
8.2
8.3
8.4
8.5
8.6
8.7
8.8
INTRODUCTION
243
ESTERIFICATION
OF
AMIDES
243
HYDROLYSIS
OF
AMIDES
248
TRANSAMIDATION
249
SUZUKI-MIYAURA
COUPLING
OF
AMIDES
255
NEGISHI
COUPLING
OF
AMIDES
258
MIZOROKI-HECK
COUPLING
OF
AMIDES
261
REDUCTION
AND
REDUCTIVE
COUPLING
OF
AMIDES
265
REFERENCES
269
9
PD-NHC
CATALYSIS
IN
CROSS-COUPLING
OF
AMIDES
273
FAEZ
S.
ALOTAIBI,
MICHAEL
R.
CHHOUN,
AND
GREGORY
R.
COOK
9.1
9.2
9.3
INTRODUCTION
273
PD(II)-NHC-CATALYZED
CROSS-COUPLING
REACTIONS
OF
AMIDES
274
PD(NHC)(ALLYL)CL
PRECATALYST
IN
SUZUKI-MIYAURA
CROSS-COUPLING
OF
AMIDES
275
9.4
PD(N3-1-T-BU-INDENYL)(IPR)CL-CATALYZED
SUZUKI-MIYAURA
CROSS-COUPLING
OF
AMIDES
279
9.5
PD-PEPPSSI
PRECATALYST
IN
THE
SUZUKI-MIYAURA
CROSS-COUPLING
OF
AMIDES
281
9.6
VARIOUS
PD-NHC
PRECATALYSTS
SUITABLE
FOR
CROSS-COUPLING
OF
AMIDES
286
9.7
CONCLUSION
288
REFERENCES
288
10
CROSS-COUPLING
OF
AMIDES
THROUGH
DECARBONYLATION
293
HONG
LU
AND
HAO
WEI
10.1
10.2
10.2.1
10.2.2
10.3
10.3.1
10.3.2
10.3.3
10.4
INTRODUCTION
293
DECARBONYLATION
OF
CYCLIC
AMIDE
DERIVATIVES
294
PHTHALIMIDES
295
SACCHARINS
AND
OTHER
CYCLIC
AMIDE
DERIVATIVES
297
DECARBONYLATION
OF
ACYCLIC
AMIDE
DERIVATIVES
298
N-ACYL-GLUTARIMIDES
298
N-ACYLSACCHARIN
AMIDES
302
OTHER
ACYCLIC
AMIDES
302
CONCLUSION
305
REFERENCES
305
CONTENTS
11
TRANSITION
METAL-CATALYZED
RADICAL
REACTIONS
OF
AMIDES
307
TALINE
KERACKIAN,
DIDIER
BOUYSSI,
NUNO
MONTEIRO,
AND
ABDERRAHMANE
AMGOUNE
11.1
11.2
INTRODUCTION
307
REACTIONS
INVOLVING
AMIDES
AS
PRECURSORS
TO
ORGANOMETALLIC
COMPOUNDS
308
11.2.1
RADICAL
REACTIONS
OF
AMIDES
VIA
METAL-CATALYZED
C-N
BOND
ACTIVATION
308
11.2.1.1
11.2.1.2
11.2.2
11.2.2.1
11.2.2.2
11.3
REDUCTIVE
CROSS-ELECTROPHILE
CROSS-COUPLING
REACTIONS
309
PHOTOREDOX
CROSS-COUPLING
REACTIONS
312
CHELATION-ASSISTED
RADICAL
REACTIONS
OF
AMIDES
316
AMIDE-DIRECTED
C-H
BOND
FUNCTIONALIZATION
316
AMIDE-DIRECTED
FUNCTIONALIZATION
OF
UNACTIVATED
ALKENES
318
REACTIONS
INVOLVING
AMIDES
AS
PRECURSORS
TO
NITROGEN
OR
CARBON-CENTERED
RADICALS
323
11.3.1
11.3.1.1
11.3.1.2
11.3.2
11.3.2.1
REACTIONS
OF
AMIDES
VIA
AMIDYL
RADICALS
323
VICINAL
DIFUNCTIONALIZATION
OF
PENDANT
OLEFINS
324
DISTANT
C-H
BOND
FUNCTIONALIZATION
325
REACTIONS
OF
AMIDES
VIA
A-AMINOALKYL
RADICALS
328
C-H
BOND
FUNCTIONALIZATION
VIA
RADICAL
ADDITION
TO
ALKENES
328
11.3.2.2
11.3.3
11.4
C-H
BOND
FUNCTIONALIZATION
VIA
CROSS-COUPLING
329
REACTIONS
OF
AMIDES
VIA
CARBAMOYL
RADICALS
331
CONCLUSION
333
REFERENCES
334
12
WEINREB
AMIDE
AS
A
MULTIFACETED
DIRECTING
GROUP
IN
C-H
ACTIVATION
339
JAYABRATA
DAS
AND
DEBABRATA
MAITI
12.1
12.2
12.2.1
12.2.2
12.2.3
12.2.4
12.2.5
12.3
12.4
INTRODUCTION
339
WEINREB
AMIDE-DIRECTED
C(SP
2
)-H
ACTIVATION
340
RU-CATALYZED
REACTIONS
340
CO-CATALYZED
REACTIONS
344
PD-CATALYZED
REACTIONS
346
RH-CATALYZED
REACTIONS
352
IR-CATALYZED
REACTIONS
354
WEINREB
AMIDE-DIRECTED
C(SP
3
)-H
ACTIVATION
359
CONCLUSIONS
AND
OUTLOOK
362
REFERENCES
362
CONTENTS
|
XI
13
COMPUTATIONAL
STUDIES
OF
AMIDE
C-N
BOND
ACTIVATION
365
XIN
HONG,
PEI-PEI
XIE,
ZHI-XIN
QIN,
AND
SHUO-QING
ZHANG
13.1
INTRODUCTION
365
13.2
GENERAL
MECHANISMS
OF
AMIDE
C-N
BOND
CLEAVAGE
AND
DERIVATIZATION
367
13.3
COMPUTATIONAL
STUDIES
ON
THE
MECHANISM
AND
SELECTIVITY
OF
LEWIS
ACID-MEDIATED
NUCLEOPHILIC
SUBSTITUTION
OF
AMIDES
368
13.3.1
COMPUTATIONAL
STUDIES
ON
THE
MECHANISM
AND
SELECTIVITY
OF
LIHMDS-MEDIATED
TRANSAMIDATION
369
13.3.2
COMPUTATIONAL
STUDIES
ON
THE
MECHANISM
AND
REACTIVITY
OF
ZN
CATALYZED
ESTERIFICATION
OF
AMIDES
373
13.3.3
COMPUTATIONAL
STUDIES
ON
THE
MECHANISM
OF
AMMONIUM
SALT-MEDIATED
HYDRAZINOLYSIS
OF
AMIDES
375
13.3.4
COMPUTATIONAL
STUDIES
ON
THE
MECHANISM
OF
ORGANOCATALYTIC
ASYMMETRIC
ALCOHOLYSIS
OF
N-SULFONYL
AMIDE
378
13.4
COMPUTATIONAL
STUDIES
ON
THE
MECHANISM
AND
SELECTIVITY
OF
TRANSITION
METAL
CATALYZED
CROSS-COUPLING
OF
AMIDES
380
13.4.1
COMPUTATIONAL
STUDY
ON
THE
MECHANISM
AND
REACTIVITY
OF
NI-CATALYZED
ESTERIFICATION
OF
AMIDES
381
13.4.2
COMPUTATIONAL
STUDY
ON
THE
MECHANISM OF
NI-CATALYZED
SUZUKI-MIYAURA
COUPLING
OF
AMIDES
387
13.4.3
COMPUTATIONAL
STUDY
ON
THE
MECHANISM
AND
SELECTIVITY
OF
NI-CATALYZED
C-N
BOND
ACTIVATION
OF
TWISTED
AMIDES
388
13.4.4
COMPUTATIONAL
STUDY
ON
THE
STRUCTURE-ACTIVITY
RELATIONSHIP
OF
NI-CATALYZED
C-N
BOND
ACTIVATION
OF
AMIDES
391
13.4.5
COMPUTATIONAL
STUDY
ON
THE
MECHANISM
OF
PD-CATALYZED
SUZUKI-MIYAURA
COUPLING
OF
AMIDES
395
13.4.6
COMPUTATIONAL
STUDY
ON
THE
MECHANISM
OF
PD-CATALYZED
TRANSAMIDATION
OF
AMIDES
398
13.5
OUTLOOK
398
REFERENCES
399
14
ESTERS
AS
VIABLE
ACYL
CROSS-COUPLING
ELECTROPHILES
403
OMID
DANESHFAR
AND
STEPHEN
G.
NEWMAN
14.1
INTRODUCTION
403
14.2
EARLY
WORK
IN
THE
CROSS-COUPLING
OF
CARBOXYLIC
ACID
DERIVATIVES
404
14.3
DECARBONYLATIVE
COUPLING
OF
ARYL
ESTERS
408
14.3.1
MIZOROKI-HECK-TYPE
COUPLING
408
14.3.2
C-H
BIARYL
COUPLING
409
XII
CONTENTS
14.3.3
14.3.4
14.3.5
14.3.5.1
14.3.5.2
14.3.5.3
14.3.5.4
14.3.5.5
14.3.6
14.3.6.1
14.3.6.2
14.3.6.3
14.3.6.4
14.4
14.4.1
14.4.2
14.4.3
14.4.4
14.4.5
14.4.6
14.5
14.5.1
14.5.2
14.5.3
14.6
14.6.1
14.6.2
14.6.3
14.7
SUZUKI-MIYAURA
COUPLING
412
SILYLATION
AND
BORYLATION
41
7
OTHER
C-C/C-H
BOND
FORMING
REACTIONS
419
SONOGASHIRA-TYPE
COUPLINGS
419
REDUCTION
421
NEGISHI-TYPE
COUPLING
421
CYANATION
422
METHYLATION
422
OTHER
C-HETEROATOM
BOND
FORMING
REACTIONS
424
ETHERIFICATION
424
AMINATION
424
THIOETHERIFICATION
427
CARBON-PHOSPHORUS
BOND
FORMATION
428
CARBONYL
RETENTIVE
COUPLING
OF
PHENYL
ESTERS
429
SUZUKI-MIYAURA
COUPLING
429
AMIDATION
433
CROSS-ELECTROPHILE
COUPLING
434
ESTER
TRANSFER
AND
ESTER
DANCE
435
DEOXYGENATIVE
ORGANOPHOSPHORUS
COUPLING
437
ALKYNE
INSERTION
438
CARBONYL
RETENTIVE
COUPLING
OF
ALKYL
ESTERS
439
AMIDATION
439
MIZOROKI-HECK-TYPE
DOMINO
REACTIONS
441
SUZUKI-MIYAURA
COUPLING
443
DECARBONYLATIVE
COUPLINGS
OF
ALKYL
ESTERS
444
DIRECTING
GROUP
ASSISTANCE
444
METHYLATION
445
ORGANOSTANNANE
FORMATION
445
CONCLUSION
AND
OUTLOOK
446
REFERENCES
447
15
CROSS-COUPLING
OF
AROMATIC
ESTERS
BY
DECARBONYLATION
453
KEI
MUTO
AND
JUNICHIRO
YAMAGUCHI
15.1
15.2
15.3
15.4
15.5
15.6
15.7
15.8
15.9
15.10
15.11
15.12
INTRODUCTION
453
OVERVIEW
OF
DECARBONYLATIVE
COUPLING
453
DECARBONYLATIVE
MIZOROKI-HECK
REACTION
457
DECARBONYLATIVE
ALKYNE
INSERTIONS
459
SUZUKI-MIYAURA
COUPLING
460
NEGISHI
COUPLING
463
SONOGASHIRA
COUPLING
464
A-ARYLATION
465
CYANATION
465
C-H
ARYLATION
466
C-N
BOND
FORMATIONS
470
C-P
BOND
FORMATION
471
CONTENTS
XIII
15.13
ETHERIFICATION
473
15.14
15.15
15.16
15.17
15.18
THIOETHERIFICATION
473
HYDROGENATION
473
BORYLATION,
SILYLATION,
AND
STANNYLATION
475
MISCELLANEOUS
478
SUMMARY
483
REFERENCES
483
INDEX
487 |
| any_adam_object | 1 |
| any_adam_object_boolean | 1 |
| author2 | Szostak, Michal |
| author2_role | edt |
| author2_variant | m s ms |
| author_GND | (DE-588)1190908603 |
| author_facet | Szostak, Michal |
| building | Verbundindex |
| bvnumber | BV048847374 |
| classification_rvk | VK 5020 VK 5500 VK 7400 VK 7402 |
| ctrlnum | (OCoLC)1369156108 (DE-599)DNB1251016413 |
| dewey-full | 547.042 |
| dewey-hundreds | 500 - Natural sciences and mathematics |
| dewey-ones | 547 - Organic chemistry |
| dewey-raw | 547.042 |
| dewey-search | 547.042 |
| dewey-sort | 3547.042 |
| dewey-tens | 540 - Chemistry and allied sciences |
| discipline | Chemie / Pharmazie |
| discipline_str_mv | Chemie / Pharmazie |
| format | Book |
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| genre_facet | Aufsatzsammlung |
| id | DE-604.BV048847374 |
| illustrated | Illustrated |
| index_date | 2024-07-03T21:39:21Z |
| indexdate | 2024-07-10T09:47:42Z |
| institution | BVB |
| institution_GND | (DE-588)16179388-5 |
| isbn | 9783527348312 352734831X |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-034112705 |
| oclc_num | 1369156108 |
| open_access_boolean | |
| owner | DE-11 DE-19 DE-BY-UBM |
| owner_facet | DE-11 DE-19 DE-BY-UBM |
| physical | xvi, 503 Seiten Illustrationen, Diagramme |
| publishDate | 2023 |
| publishDateSearch | 2023 |
| publishDateSort | 2023 |
| publisher | Wiley-VCH |
| record_format | marc |
| spelling | Amide bond activation concepts and reactions edited by Michal Szostak Weinheim Wiley-VCH [2023] ©2023 xvi, 503 Seiten Illustrationen, Diagramme txt rdacontent n rdamedia nc rdacarrier Organische Synthese (DE-588)4075695-6 gnd rswk-swf Übergangsmetallverbindungen (DE-588)4061385-9 gnd rswk-swf Amide (DE-588)4279702-0 gnd rswk-swf Chemische Bindung (DE-588)4009843-6 gnd rswk-swf Aktivierung Chemie (DE-588)4141761-6 gnd rswk-swf Chemie Chemistry Computational Chemistry & Molecular Modeling Computational Chemistry u. Molecular Modeling Organic Chemistry Organische Chemie Pharmaceutical & Medicinal Chemistry Pharmazeutische u. Medizinische Chemie CH60: Pharmazeutische u. Medizinische Chemie CH80: Organische Chemie CHD0: Computational Chemistry u. Molecular Modeling Technische u. Industrielle Chemie Amidbindung Industrial Chemistry CH30: Technische u. Industrielle Chemie (DE-588)4143413-4 Aufsatzsammlung gnd-content Amide (DE-588)4279702-0 s Aktivierung Chemie (DE-588)4141761-6 s Chemische Bindung (DE-588)4009843-6 s Übergangsmetallverbindungen (DE-588)4061385-9 s Organische Synthese (DE-588)4075695-6 s DE-604 Szostak, Michal (DE-588)1190908603 edt Wiley-VCH (DE-588)16179388-5 pbl Erscheint auch als Online-Ausgabe, PDF 978-3-527-83024-4 Erscheint auch als Online-Ausgabe, EPUB 978-3-527-83026-8 Erscheint auch als Online-Ausgabe, oBook 978-3-527-83025-1 X:MVB http://www.wiley-vch.de/publish/dt/books/ISBN978-3-527-34831-2/ Kurzbeschreibung B:DE-101 application/pdf https://d-nb.info/1251016413/04 Inhaltsverzeichnis DNB Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=034112705&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis 1\p dnb 20230201 DE-101 https://d-nb.info/provenance/plan#dnb |
| spellingShingle | Amide bond activation concepts and reactions Organische Synthese (DE-588)4075695-6 gnd Übergangsmetallverbindungen (DE-588)4061385-9 gnd Amide (DE-588)4279702-0 gnd Chemische Bindung (DE-588)4009843-6 gnd Aktivierung Chemie (DE-588)4141761-6 gnd |
| subject_GND | (DE-588)4075695-6 (DE-588)4061385-9 (DE-588)4279702-0 (DE-588)4009843-6 (DE-588)4141761-6 (DE-588)4143413-4 |
| title | Amide bond activation concepts and reactions |
| title_auth | Amide bond activation concepts and reactions |
| title_exact_search | Amide bond activation concepts and reactions |
| title_exact_search_txtP | Amide bond activation concepts and reactions |
| title_full | Amide bond activation concepts and reactions edited by Michal Szostak |
| title_fullStr | Amide bond activation concepts and reactions edited by Michal Szostak |
| title_full_unstemmed | Amide bond activation concepts and reactions edited by Michal Szostak |
| title_short | Amide bond activation |
| title_sort | amide bond activation concepts and reactions |
| title_sub | concepts and reactions |
| topic | Organische Synthese (DE-588)4075695-6 gnd Übergangsmetallverbindungen (DE-588)4061385-9 gnd Amide (DE-588)4279702-0 gnd Chemische Bindung (DE-588)4009843-6 gnd Aktivierung Chemie (DE-588)4141761-6 gnd |
| topic_facet | Organische Synthese Übergangsmetallverbindungen Amide Chemische Bindung Aktivierung Chemie Aufsatzsammlung |
| url | http://www.wiley-vch.de/publish/dt/books/ISBN978-3-527-34831-2/ https://d-nb.info/1251016413/04 http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=034112705&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT szostakmichal amidebondactivationconceptsandreactions AT wileyvch amidebondactivationconceptsandreactions |
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