Metal catalyzed cross coupling reactions:
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| Format: | Book |
|---|---|
| Language: | German |
| Published: |
Weinheim [u.a.]
Wiley-VCH
1998
|
| Edition: | Reprint. |
| Subjects: | |
| Online Access: | Inhaltsverzeichnis |
| Item Description: | Literaturangaben. - 2. Aufl. mehrbändig |
| Physical Description: | XXI, 517 S. graph. Darst. |
| ISBN: | 352729421X |
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| 245 | 1 | 0 | |a Metal catalyzed cross coupling reactions |c ed. by François Diederich ... |
| 250 | |a Reprint. | ||
| 264 | 1 | |a Weinheim [u.a.] |b Wiley-VCH |c 1998 | |
| 300 | |a XXI, 517 S. |b graph. Darst. | ||
| 336 | |b txt |2 rdacontent | ||
| 337 | |b n |2 rdamedia | ||
| 338 | |b nc |2 rdacarrier | ||
| 500 | |a Literaturangaben. - 2. Aufl. mehrbändig | ||
| 650 | 0 | 7 | |a Katalyse |0 (DE-588)4029921-1 |2 gnd |9 rswk-swf |
| 650 | 0 | 7 | |a Metallverbindungen |0 (DE-588)4169640-2 |2 gnd |9 rswk-swf |
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| 689 | 0 | 1 | |a Katalyse |0 (DE-588)4029921-1 |D s |
| 689 | 0 | 2 | |a Metallverbindungen |0 (DE-588)4169640-2 |D s |
| 689 | 0 | |5 DE-604 | |
| 700 | 1 | |a Diederich, François |d 1952-2020 |e Sonstige |0 (DE-588)109354419 |4 oth | |
| 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=007843420&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |3 Inhaltsverzeichnis |
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CONTENTS
1
PALLADIUM
OR
NICKEL-CATALYZED
CROSS-COUPLING
WITH
ORGANOMETALS
CONTAINING
ZINC,
MAGNESIUM,
ALUMINUM,
AND
ZIRCONIUM
EI-ICHI
NEGISHI,
FANG
LIU
1.1
INTRODUCTION
.
1
1.2
SYSTEMATIC
SURVEY
OF
PALLADIUM-OR
NICKEL-CATALYZED
CROSS-COUPLING
.
.
4
1.2.1
SCOPE
WITH
RESPECT
TO
METAL
COUNTERIONS
AND
INHIBITION
OF
CATALYSIS
BY
ORGANOLITHIUMS
.
4
1.2.2
CROSS-COUPLING
BETWEEN
TWO
UNSATURATED
CARBON
GROUPS
.
6
1.2.2.1
PALLADIUM-CATALYZED
CROSS-COUPLING
INVOLVING
ALKYNYLMETALS
AND
RELATED
ALKYNYL
NUCLEOPHILES:
ALKYNYL-ARYL,
ALKYNYL-ALKENYL,
AND
ALKYNYL-ALKYNYL
COUPLING
.
6
1.2.2.2
HYDROMETALLATION
CROSS-COUPLING
AND
CARBOMETALLATION
-
CROSS-COUPLING
TANDEM
PROTOCOLS
AND
OTHER
ALKENYL-ARYL,
ALKENYL-ALKENYL,
AND
ALKENYL
ALKYNYL
COUPLING
REACTIONS:
DOUBLE
METAL
CATALYSIS
.
7
1.2.2.3
ARYL-ARYL
COUPLING
.
10
1.2.3
PALLADIUM-CATALYZED
CROSS-COUPLING
INVOLVING
ALKYL
GROUPS
WITHOUT
PROXIMAL
UNSATURATION
.
12
1.2.4
CROSS-COUPLING
INVOLVING
ALLYL,
BENZYL,
AND PROPARGYL
GROUPS
.
16
1.2.4.1
COUPLING
REACTIONS
OF
ALKENYL
AND
ARYLMETALS
WITH
ALLYL,
BENZYL,
AND
PROPARGYL
ELECTROPHILES
.
16
1.2.4.2
CROSS-COUPLING
WITH
ALLYL
AND
BENZYLMETALS
.
18
1.2.5
CROSS-COUPLING
INVOLVING
CARBONYL
COMPOUNDS
.
18
1.2.5.1
PALLADIUM-CATALYZED
ACYLATION
OF
ORGANOMETALS
WITH
ACYL HALIDES.
.
18
1.2.5.2
PALLADIUM-CATALYZED
ALLYLATION
AND
RELATED
REACTIONS
OF
ENOLATES
.
19
1.2.5.3
^-SUBSTITUTION
OF
CARBONYL
COMPOUNDS
WITH
UNSATURATED
CARBON
GROUPS
.
21
1.2.6
LEAVING
GROUPS
.
24
1.2.7
LIGANDS
.
26
1.3
ASSYMETRIC
CROSS-COUPLING
.
27
1.4
PALLADIUM-CATALYZED
TANDEM
PROCESSES
INVOLVING
CROSS-COUPLING
REACTIONS
.
30
1.5
MECHANISM
OF
CROSS-COUPLING
.
34
1.6
CONCLUSIONS
.
37
XII
CONTENTS
1.7
REPRESENTATIVE
EXPERIMENTAL
PROCEDURES
.
39
1.7.1
P-METHOXYPHENYLETHYNE
.
39
1.7.1.1
PREPARATION
OF
ETHYNYLZINC
CHLORIDE
.
39
1.7.1.2
PREPARATION
OF
P-METHOXYPHENYLETHYNE
.
39
1.7.2
(7E,9E,11E,13E)-RETINOL
(VITAMIN
A)
.
40
1.7.3
A-FAMESENE
.
41
1.7.4
(Z)-L-[L'-METHYL-(E)-2'-HEPTENYLIDENE]INDAN
.
41
ABBREVIATIONS
.
42
REFERENCES
.
42
2
CROSS-COUPLING
REACTIONS
OF
ORGANOBORON
COMPOUNDS
WITH
ORGANIC
HALIDES
AKIRA
SUZUKI
2.1
INTRODUCTION
.
49
2.2
PREPARATION
OF
ORGANOBORON
COMPOUNDS
.
49
2.2.1
HYDROBORATION
OF
ALKENES
AND
ALKYNES
.
49
2.2.2
HALOBORATION
OF
TERMINAL
ALKYNES
.
51
2.2.3
PREPARATION
FROM
ORGANOLITHIUM
AND
MAGNESIUM
REAGENTS
.
52
2.2.4
MISCELLANEOUS
METHODS
.
53
2.3
PALLADIUM-CATALYZED
REACTIONS
OF
ORGANOBORON
COMPOUNDS
AND
THEIR
MECHANISM
.
54
2.3.1
CROSS-COUPLING
REACTIONS
.
54
2.3.2
OTHER
REACTIONS
CATALYZED
BY
TRANSITION-METAL
COMPLEXES
.
61
2.4
CROSS-COUPLING
REACTIONS
OF
ORGANOBORON
COMPOUNDS
.
63
2.4.1
COUPLING
OF
1
-ALKENYLBORON
DERIVATIVES:
SYNTHESIS
OF
CONJUGATED
DIENES
.
63
2.4.2
COUPLING
OF
ARYLBORON
COMPOUNDS:
SYNTHESIS
OF
BIARYLS
.
70
2.4.3
COUPLING
OF
ALKYBORON
DERIVATIVES
.
74
2.4.4
REACTIONS
WITH
TRIFLATES
.
79
2.4.5
CARBONYLATIVE
COUPLING
.
81
2.5
CONCLUSIONS
.
82
2.6
EXPERIMENTAL
PROCEDURES
.
84
2.6.1
REACTION
OF
1
-ALKENYLBORONATES
WITH
VINYLIC
HALIDES:
SYNTHESIS
OF
(1Z,
3E)-1-PHENYL-1,3-OCTADIENE
.
84
2.6.1.1
(E)-L-HEXENYL
1,3,
2-BENZODIOXABOROLE
.
84
2.6.1.2
(1Z,
3E)-1-PHENYL-1,3-OCTADIENE
.
85
2.6.2
REACTION
OF
ARYLBORONIC
ACIDS
WITH
HALOARENES:
SYNTHESIS
OF
STERICALLY
HINDERED
BIARYLS
.
85
2.6.3
REACTION
OF
9-ALKYL-9-BORABICYCLO[3.3.1]NONANE
WITH
1-BROMO-L
PHENYLTHIOETHENE:
SYNTHESIS
OF
4-(3-CYCLOHEXENYL)-2-PHENYLTHIO-L-BUTENE
.
86
2.6.3.1
1
-BROMO-1-PHENYLTHIOETHENE
.
86
2.6.3.2
9-[2-(3-CYCLOHEXENYL)ETHYL]-9-BBN
.
86
CONTENTS
XIII
2.6.3.3
4-(3-CYCLOHEXENYL)-3-PHENYLETHIO-L-BUTENE
.
87
2.6.4
INTRAMOLECULAR
CROSS-COUPLING
OF
ENOL
TRIFLATES
WITH
ORGANOBORON
COMPOUNDS:
SYNTHESIS
OF
2,3-TRIMETHYLENE-3-CARBOMETHOXYCYCLOHEPTENE
88
2.6.4.1
2-ALLYL-2-CARBOMETHOXYCYCLO-7-HEPTENYL
TRIFLATE
.
88
2.6.4.2
2,3-TRIMETHYLENE-3-CARBOMETHOXYCYCLO-7-HEPTENE
.
88
2.6.5
CARBONYLATIVE
COUPLING
REACTION:
SYNTHESIS
OF
()-5-PENTADECEN-7-ONE
.
88
ABBREVIATIONS
.
89
REFERENCES
.
89
3
PALLADIUM-CATALYZED
COUPLING
OF
ORGANYL
HALIDES
TO
ALKENES
-
THE
HECK
REACTION
STEFAN
BRASE,
ARMIN
DE
MEIJERE
3.1
INTRODUCTION
.
99
3.2
PRINCIPLES
.
99
3.2.1
THE
MECHANISM
.
99
3.2.2
THE
CATALYSTS
.
101
3.2.3
THE
ALKENES
.
102
3.2.4
EFFECTS
OF
BASES,
LIGANDS,
AND
ADDITIVES
.
105
3.2.5
THE
LEAVING
GROUPS
.
107
3.2.6
STEREOCHEMICAL
REQUIREMENTS
IN
INTRAMOLECULAR
CYCLIZATIONS
.
112
3.3
CASCADE
REACTIONS
AND
MULTIPLE
COUPLINGS
.
114
3.3.1
HECK
CASCADES
INVOLVING
SP
2
CENTERS
.
115
3.3.2
HECK-REACTION
CASCADES
INVOLVING
SP
2
AND
SP
CENTERS
.
116
3.3.3
CASCADES
CONSISTING
OF
HECK
AND
SUBSEQUENT
CYCLOADDITION
OR
ELECTROCYCLIZATION
REACTIONS
.
117
3.3.3.1
HECK
AND
DIELS-ALDER
CASCADES
.
117
3.3.3.2
HECK
(VR-ELECTROCYCLIZATION
CASCADES
.
118
3.3.4
HECK
COMBINED
WITH
OTHER
CROSS-COUPLING
PROCESSES
.
121
3.3.5
PALLADIUM-CATALYZED
REACTIONS
WITH
NUCLEOPHILIC
SUBSTRATES
.
122
3.3.6
HECK-ALDOL
AND
HECK-MICHAEL
CASCADES
.
126
3.3.7
C
-
H
ACTIVATION
IN
HECK-TYPE
PROCESSES
.
127
3.3.8
HECK
WITH
CONSECUTIVE
CARBONYLATION
REACTIONS
.
130
3.3.9
MULTIPLE
HECK
COUPLINGS
.
130
3.4
RELATED
PALLADIUM-CATALYZED
REACTIONS
.
133
3.5
ENANTIOSELECTIVE
HECK-TYPE
REACTIONS
.
134
3.6
SYNTHESES
OF
NATURAL
PRODUCTS
AND
BIOLOGICALLY
ACTIVE
COMPOUNDS
.
139
3.7
CONCLUSIONS
.
141
3.8
EXPERIMENTAL
PROCEDURES
.
148
3.8.1
DIPOTASSIUM
(E)-4,
4'
-DIPHENYLSTILBENE-4"-4"'-DISULFONATE
(STILBENE
I)
.
.
148
3.8.2
TRANS-4-ACETYLSTILBENE
.
149
XIV
CONTENTS
3.8.3
METHYL
3-(E)-(2-[2-(E)-METHOXYCARBONYLETHENYL]CYCLOPENT-L-ENYL}
ACRYLATE
.
150
3.8.4
DIETHYL
4'-CHLORO-4'-METHOXYCARBONYLSPIRO[CYCLOPROPANE-L,3'
BICYCLO[4.3.0]NON-R(6')-ENE]-8',8'-DICARBOXYLATE
.
150
3.8.5
(R)-2-CYCLOHEXENYL-2,5-DIHYDROFURAN
.
151
3.8.6
METHOXY-L-(S)-ETHENYL
1,2,3,
4-TETRAHYDRONAPHTHALENE
.
151
ACKNOWLEDGMENTS
.
152
ABBREVIATIONS
AND
ACRONYMS
.
152
REFERENCES
.
154
4
ORGANOTIN
REAGENTS
IN
CROSS-COUPLING
TERENCE
N.
MITCHELL
4.1
INTRODUCTION
.
167
4.2
STILLE
COUPLING
OF
ALKENYLTINS
.
167
4.2.1
INTERMOLECULAR
REACTIONS
.
168
4.2.1.1
REACTIONS
INVOLVING
ORGANIC
HALIDES
AND
TRIFLATES
.
168
4.2.1.2
REACTIONS
INVOLVING
ACID
CHLORIDES
.
170
4.2.1.3
REACTIONS
INVOLVING
ALLYL
CARBONATES
.
171
4.2.2
INTRAMOLECULAR
REACTIONS
.
172
4.2.3
REACTIONS
OF
DISTANNYLALKENES
.
173
4.2.4
LESS
CONVENTIONAL
REACTIONS
.
175
4.2.5
MECHANISTIC
CONSIDERATIONS
AND
THE
CHOICE
OF
CATALYST
.
178
4.3
REACTIONS
OF
SUBSTRATES
WHERE
TIN
IS
ATTACHED
TO
A
HETEROCYCLIC
RING
.
.
.
179
4.3.1
STANNYLFURANS,-THIOPHENES,
AND-PYRROLES
.
179
4.3.2
STANNYLPYRIDINES
(AND-QUINOLINES)
.
180
4.3.3
STANNYLINDOLES
.
182
4.3.4
OTHER
HETEROCYCLES
.
182
4.4
REACTIONS
OF
ARYLTINS
.
182
4.4.1
REACTIONS
WITH
TRIFLATES
.
182
4.4.2
REACTIONS
WITH
HALIDES
.
183
4.5
REACTIONS
OF
ALKYNYLTINS
.
185
4.6
REACTIONS
OF
ALKYLTINS
.
187
4.7
REACTIONS
INVOLVING
VARIOUS
TYPES
OF
TETRAORGANOTIN
.
187
4.8
REACTIONS
OF
ALLYL-,
ALLENYL-,
AND
PROPARGYLTINS
.
188
4.9
RELATED
PALLADIUM-CATALYZED
REACTIONS
.
189
4.9.1
REACTIONS
OF
DITINS
(AND
SILYLSTANNANES)
.
189
4.9.1.1
CROSS-COUPLING
REACTIONS
.
190
4.9.1.2
ADDITION
REACTIONS
.
190
4.9.2
REACTIONS
OF
TIN
HYDRIDES
.
190
4.9.3
REACTIONS
OF
TIN
ALKOXIDES,
THIOALKOXIDES,
AND
STANNYLAMINES
.
192
CONTENTS
XV
4.10
REACTIONS
INDUCED
BY
COPPER
.
192
4.11
NICKEL-CATALYZED
REACTIONS
.
193
4.12
MECHANISTIC
DISCUSSION
AND
CONCLUSION
.
194
4.13
EXPERIMENTAL
PROCEDURES
.
195
4.13.1
INDANOMYCIN
.
195
4.13.2
7V,7V'-BIS(TRIFLUOROMETHANESULFONYL)PAPUAMINE.
196
4.13.3
RAPAMYCIN
.
196
4.13.4
A
NICKEL-CATALYZED
PROCEDURE:
L-PHENYLPENT-4-EN-L-YNE
.
196
ABBREVIATIONS
.
197
REFERENCES
.
197
5
CROSS-COUPLING
REACTIONS
TO
SP
CARBON ATOMS
KENKICHI
SONOGASHIRA
5.1
INTRODUCTION
.
203
5.2
CROSS-COUPLING
REACTIONS
OF
ALKYNYLMETAL
REAGENTS
WITH
SP
2
CARBON
ATOMS
.
203
5.2.1
ALKYNYLCOPPER
REAGENTS
.
203
5.2.2
ALKYNYLBORANE
REAGENTS
.
205
5.3
TRANSITION-METAL-CATALYZED
CROSS-COUPLING
.
206
5.3.1
ALKY
NYLZINC
REAGENTS
.
206
5.3.2
ALKYNYLTIN
REAGENTS
.
208
5.3.3
ALKYNYLMAGNESIUM
REAGENTS
.
211
5.3.4
ALKYNYLBORANE
REAGENTS
.
212
5.3.5
TERMINAL
ACETYLENE
WITH
SP
2
-
CARBON
HALIDES
.
213
5.3.5.1
SYNTHESIS
OF
INTERNAL
ACETYLENES
.
213
5.3.5.2
SYNTHESIS
OF
TERMINAL
ACETYLENES
.
216
5.3.5.3
STEREOSPECIFIC
SYNTHESIS
.
220
5.3.5.6
CROSS-COUPLING
OF
HALOALKYNES
WITH
ORGANOMETALLIC
COMPOUNDS
.
.
.
.
222
5.4
CONCLUSIONS
.
223
5.5
EXPERIMENTAL
PROCEDURES
.
224
5.5.1
UNDECA-3,5-DIYN-L-OL
.
224
5.5.2
ALK-3,5-DIYN-L-OL
.
224
5.5.3
(E)-5-UNDECEN-3-YN-L-OL
.
224
5.5.4
DIPHENYLACETYLENE
.
225
5.5.5
4-PHENYLBUT-L-EN-3-YNE
.
225
5.5.6
P-NITROETHYNYLBENZENE
.
226
5.5.7
(7Z)-7-PENTADECEN-5,9-YN-L-OL
.
226
5.5.8
TERMINAL
ACETYLENE
BY
POTASSIUM-HYDROXIDE-CATALYZED
RETRO-FAVORSKY
REACTION
.
226
ABBREVIATIONS
.
227
REFERENCES
.
227
XVI
CONTENTS
6
INTRAMOLECULAR
HECK
REACTIONS
IN
NATURAL
PRODUCT
CHEMISTRY
J.
T.
LINK,
LARRY
E.
OVERMAN
6.1
INTRODUCTION
.
231
6.2
MECHANISTIC
OUTLINE
.
231
6.3
RING
SYNTHESIS
.
233
6.3.1
FIVE-MEMBERED
RINGS
.
233
6.3.2
SIX-MEMBERED
RINGS
.
236
6.3.3
SEVEN-MEMBERED
RINGS
.
242
6.3.4
EIGHT-MEMBERED
RINGS
.
243
6.3.5
LARGE
RINGS
.
244
6.4
CYCLOISOMERIZATION
OF
ENYNES
.
246
6.5
TANDEM
REACTIONS
.
248
6.6
ASYMMETRIC
REACTIONS
.
256
6.7
CONCLUDING
COMMENTS
.
260
6.8
REPRESENTATIVE
EXPERIMENTAL
PROCEDURES
.
'
.
.
261
6.8.1
GENERAL
COMMENTS
ABOUT
CATALYSTS,
REAGENTS,
AND
CONDITIONS
.
261
6.8.2
[7A,8A]-DISPIRO[L,3-DIOXOLANE-2,R-CYCLOHEX-2'-ENE-4',8
W
-
7"[(METHOXYCARBONYL)AMINOMETHYL][5H-L,3]DIOXO[4,5-G][2]BENZOPYRAN]
263
6.8.3
(
-
)-5,6-DEHYDRO
17-[
10,11
-DIHYDRO-5#-DIBENZO[A,
TFLCYCLOHEPTEN-5-YL]
4-BENZYLOXY-3-METHOXYMORPHINAN
.
263
6.8.4
(5/J,17/?)-(P-METHOXYBENZYL)OXYMETHYL-5,19-METHYLENEDIOXYANDROSTAN
1,8(14),9(1
L)-TRIENE
.
263
6.8.5
(2R*,4A5*,7S'*,9A5*)-2-HYDROXY-4-(4-HYDROXYBUTYL)-7-METHYL-L,2,5,6,7,
9A-HEXAHYDRO-4A,7-METHANO-4AH-BENZOCYCLOHEPTENE
.
264
6.8.6
(5)-3-FORMYLMETHYL
1
,2-DIHYDRO-5-METHOXY
1
,3-DIMETHYL-2-OXO
[3/7]INDOLE
.
265
ABBREVIATIONS
.
266
REFERENCES
.
266
7
CARBOMETALLATION
REACTIONS
HANE
MAREK,
JEAN
F.
NORMANT
7.1
INTRODUCTION
.
271
7.2
CARBOMETALLATION
OF
ALKYNES
.
271
7.2.1
INTERMOLECULAR
CARBOMETALLATION
.
271
7.2.2
INTRAMOLECULAR
CARBOMETALLATION
.
276
7.2.2.1
FIVE-MEMBERED
RING
SYNTHESIS
.
276
7.2.2.2
FOUR-MEMBERED
RING
SYNTHESIS
.
282
7.2.2.3
SIX-MEMBERED RING
SYNTHESIS
.
282
CONTENTS
XVII
7.3
CARBOMETALLATION
OF
ALLENES
.
283
7.3.1
INTRAMOLECULAR
CARBOMETALLATION
.
283
7.3.2
INTENNOLECULAR
CARBOMETALLATION
.
286
7.4
CARBOMETALLATION
OF
CONJUGATED
ENYNES
.
287
7.4.1
INTERMOLECULAR
CARBOMETALLATION
.
287
7.4.2
INTRAMOLECULAR
CARBOLITHIATION
OF
CONJUGATED
SILYLATED
ENYNES
.
287
7.5
CARBOMETALLATION
OF
ALKENES
.
289
7.5.1
INTRAMOLECULAR
CARBOMETALLATION
.
290
7.5.1.1
FIVE-MEMBERED
RING
SYNTHESIS
.
290
7.5.1.2
SIX-MEMBERED
RING
SYNTHESIS
.
304
7.5.1.3
FOUR-MEMBERED
RING
SYNTHESIS
AND
REARRANGEMENTS
OF
BIS(HOMOALLYL)
METALS
.
305
7.5.1.4
THREE-MEMBERED
RING
SYNTHESIS
.
306
7.5.1.5
FIVE-MEMBERED
RING
SYNTHESIS
VIA
CYCLIZATION
OF
VINYLLITHIUM
DERIVATIVES
306
7.5.2
INTERMOLECULAR
CARBOMETALLATION
.
307
7.6
ENANTIOSELECTIVE
CARBOMETALLATION
OF
ALKENES
.
322
7.7
CONCLUSIONS
.
328
7.8
EXPERIMENTAL
PROCEDURES
.
329
7.8.1
(E)-L-CHLORO-2-ALLYL-3-TERT-BUTOXY)HEX-L-ENE
.
329
7.8.2
GENERAL
PROCEDURE
FOR
THE
CYCLIZATION
INVOLVING
RIEKE
'
S
ACTIVATED
ZINC
.
330
7.8.3
TYPICAL
PROCEDURE
FOR
THE
CYCLIZATION
OF
PROPARGYLIC
ORGANOZINC
REAGENTS
330
7.8.4
ANTZ-(3S*,4R*)-DIMETHYLNON-L-ENE
.
331
7.8.5
(S)-2-BENZYLHEXAN-L-OL
.
331
ABBREVIATIONS
.
331
REFERENCES
AND
NOTES
.
332
8
PALLADIUM-CATALYZED
1,4-ADDITIONS
TO
CONJUGATED
DIENES
JAN-E.
BACKVALL
8.1
INTRODUCTION
.
339
8.2
PALLADIUM(0)-CATALYZED
REACTIONS
.
339
8.2.1
ADDITION
OF
H-NU
.
340
8.2.1.1
1,4-HYDROSILYLATION
.
340
8.2.1.2
1,4-HYDROSTANNATION
.
342
8.2.1.3
1,4-HYDROAMINATION
.
342
8.2.1.4
ADDITION
OF
ACTIVE
METHYLENE
COMPOUNDS
.
343
8.2.1.5
1,4-HYDROSULFONATION
.
344
8.2.1.6
1,4-HYDROBORATION
.
344
8.2.1.7
1,4-HYDROCYANATION
.
345
8.2.2
1,4-COUPLING
WITH
R~
AND
NU
.
345
8.2.2.1
1,4-CARBOAMINATION
.
346
XVIII
CONTENTS
8.2.2.2
1,4
ADDITION
OF
R
_
(ARYL
OR
VINYL)
AND
STABILIZED
CARBANIONS
.
347
8.2.2.3
1,4
ADDITION
OF
CARBON
AND
OXYGEN
NUCLEOPHILES
.
349
8.2.2.4
1,4-CARBOSILYLATION
.
350
8.3
PALLADIUM(II)-CATALYZED
REACTIONS
.
352
8.3.1
1,4
ADDITION
OF
TWO
NUCLEOPHILES
.
352
8.3.1.1
1,4-DIACYLOXYLATION
.
353
8.3.1.2
1,4-HALOACYLOXYLATION
.
364
8.3.1.3
1,4
ADDITION
OF
AN
ALKOXIDE
AND
ANOTHER
OXY
GEN
FUNCTION
OR
A
HALIDE
.
.
372
8.3.1.4
1,4-OXYAMINATION
AND
1,4-CHLOROAMINATION
.
376
8.3.1.5
INTRAMOLECULAR
1,4-ADDITIONS
WITH
C
-
C
BOND
FORMATION
.
377
8.4
EXPERIMENTAL
PROCEDURES
.
380
8.4.1
(3AS*,57?*,7AA*)-5-ACETOXY-2-OXO-2,3,3A,4,5,7A-HEXAHYDROBENZOFURAN
.
380
8.4.2
CA-4-CHLORO-3-[4-(BENZYLOXY)BUTYL]-2-CYCLOHEXEN
1-YL
ACETATE
.
380
8.4.3
(3A7?*,5S*,7A/?*)-L-(BENZYLOXYCARBONYL)-5-CHLORO-2,3,3A,4,5,7A
HEXAHY
DROINDOLE
.
381
8.4.4
(15*,4S*,67?*)-4-CHLORO-7,7-DI(METHOXYCARBONYL)-9
METHYLENEBICYCLO[4.4.0]DEC-2-ENE
.
381
ABBREVIATIONS
.
381
REFERENCES
AND
NOTES
.
382
9
CARBON-CARBON
BOND
FORMATION
REACTIONS
MEDIATED
BY
ORGANOZINC
REAGENTS
PAUL
KNOCHEL
9.1
INTRODUCTION
.
387
9.1.1
METHODS
OF
PREPARATION
OF
ZINC
ORGANOMETALLICS
.
388
9.2
UNCATALYZED
CROSS-COUPLING
REACTIONS
.
391
9.3
COPPER-CATALYZED
CROSS-COUPLING
REACTIONS
.
393
9.3.1
CROSS-COUPLING
REACTIONS
WITH
ALLYLIC
HALIDES
AND
RELATED
REACTIVE
HALIDES
393
9.3.2
CROSS-COUPLING
REACTIONS
WITH
ALKYNYL,
ALKENYL,
AND
ARYL
HALIDES
.
396
9.3.3
CROSS-COUPLING
REACTIONS
WITH
ALKYL
HALIDES
.
398
9.3.4
ACYLATION
REACTIONS
.
398
9.4
TRANSITION-METAL-CATALYZED
CROSS-COUPLING
REACTIONS
.
399
9.4.1
PALLADIUM
AND
NICKEL-CATALYZED
C
-
BOND
FORMATION
REACTIONS
.
399
9.4.1.1
ADDITION
TO
UNACTIVATED
DOUBLE
BONDS
.
399
9.4.1.2
ADDITION
TO
UNACTIVATED
TRIPLE
BONDS:
NICKEL-CATALYZED
CARBOZINCATION
.
.
403
9.4.1.3
CATALYTIC
C
SP
3-C
SP
3
CROSS-COUPLING
REACTIONS
.
403
9.4.1.4
PALLADIUM-CATALYZED
CROSS-COUPLING
BETWEEN
POLYFUNCTIONAL
UNSATURATED
SUBSTRATES
.
406
9.4.2
COBALT-,
MANGANESE-,
AND
IRON-CATALYZED
CROSS-COUPLING
REACTIONS
.
.
.
407
9.4.2.1
CARBONYLATIONS
AND
ACYLATIONS
.
407
CONTENTS
XIX
9.4.2.2
COBALT-CATALYZED
CROSS-COUPLING
REACTIONS
.
408
9.4.2.3
MANGANESE
AND
COPPER-CATALYZED
RADICAL
CYCLIZATIONS
.
409
9.5
CONCLUSIONS
.
410
9.6
EXPERIMENTAL
PROCEDURES
.
410
9.6.1
(E)-6-CHLORO-2-HEXENENITRILE
.
410
9.6.2
(3-MYRTANYL)CYCLOPENTANONE
.
410
9.6.3
QUINIDINE
DERIVATIVE
21
.
411
9.6.4
6-CHLORO-L-CYCLOHEXENYL
1
-HEXYNE
.
411
9.6.5
3-(4-PENTYNYL)-2-CYCLOHEXEN-L-ONE
.
412
9.6.6
(E)-10-PIVALOXY-5-DECENENITRILE
.
412
9.6.7
10-NITRO-9-PHENYLDECYL
ACETATE
.
412
9.6.8
2,5-DIBENZOYLTHIOPHENE
.
413
9.6.9
1
-BUTYL-L-(3-NITRO-2-PHENYLPROPYL)CYCLOPENTANE
.
413
9.6.10
ETHYL
12-ACETOXY-2-DODECANOATE
.
414
9.6.11
(E)-4-(5-CHLORO-L-PENTENYL)BENZONITRILE
.
414
9.6.12
4-CHLOROBIPHENYL
.
414
9.6.13
(4'-CHLORO-3-TRIFLUOROMETHANESULFONYLOXY)BIPHENYL
.
414
9.6.14
4"-CYANO-4-METHOXY-L,R,2',L"-TERPHENYL
.
415
9.6.15
DI(4-CHLOROBUTYL)
KETONE
.
415
9.6.16
5-OXODODECYL
PIVALATE
.
416
9.6.17
CIS-BICYCLO[4.3.0]NONAN-L-OL
.
416
ABBREVIATIONS
.
416
REFERENCES
.
416
10
ORGANOSILICON
COMPOUNDS
IN
CROSS-COUPLING
REACTIONS
TAMEJIRO
HIYAMA
10.1
INTRODUCTION
.
421
10.1.1
A
BRIEF
HISTORY
OF
THE
CROSS-COUPLING
REACTION
.
421
10.1.2
PREVIOUS
STUDIES
ON
ORGANOSILICON-BASED
CROSS-COUPLING
REACTIONS
.
.
.
421
10.1.3
ACTIVATION
OF
A
C
-
SI
BOND
BY
A
NUCLEOPHILE
.
422
10.2
COUPLING
REACTIONS
OF
ALKENYLSILANES
.
423
10.2.1
TRIMETHYL(VINYL)SILANE
.
423
10.2.2
ALKENYLSILANES
.
424
10.2.3
STEREOCHEMISTRY
.
425
10.2.4
MECHANISM
.
426
10.2.5
SYNTHETIC
APPLICATIONS
.
428
10.3
COUPLING
REACTIONS
OF
ARYLSILANES
.
429
10.3.1
PROTOTYPE
OF
BIARYL
SYNTHESIS
.
429
10.3.2
COUPLING
WITH
CHLOROBENZENE
.
432
10.3.3
USE
OF
SODIUM
HYDROXIDE
ACTIVATOR
.
432
XX
CONTENTS
10.3.4
APPLICATIONS
.
432
10.3.5
CARBONYLATIVE
COUPLING
.
433
10.3.6
MECHANISM
.
434
10.4
COUPLING
REACTIONS
OF
ALKYNYLSILANES
.
435
10.4.1
SYNTHESIS
OF
CONJUGATED
ACETYLENES
.
435
10.4.2
THREE-COMPONENT
COUPLING
REACTION
.
436
10.5
COUPLING
REACTIONS
OF
DISILANES
.
436
10.6
COUPLING
REACTIONS
OF
ALKYLSILANES
.
436
10.6.1
METHYLATION
.
436
10.6.2
ALKYLATION
.
437
10.6.3
LEAVING
GROUPS
OF
THE
COUPLING
PARTNER
.
437
10.6.4
STEREOCHEMISTRY
.
439
10.7
COUPLING
REACTIONS
OF
ALLYLSILANES
.
440
10.7.1
REGIOCHEMISTRY
.
440
10.7.2
STEREOCHEMISTRY
.
442
10.7.3
ASYMMETRIC
CHEMISTRY
.
444
10.8
COUPLING
REACTIONS
WITHOUT
FLUORIDE
ION
.
446
10.8.1
COUPLING
REACTIONS
OF
ALLYLIC
CARBONATES
.
446
10.8.2
COUPLING
REACTIONS
OF
DIENE
MONOXIDES
.
448
10.9
PROSPECTS
.
448
10.9.1
AVAILABILITY
OF
ORGANOSILICON
REAGENTS
.
448
10.9.2
THE
FUTURE
OF
THE
ORGANOSILICON-BASED
CROSS-COUPLING
REACTION
.
449
10.9.3
SUMMARY
.
449
10.10
EXPERIMENTAL
PROCEDURES
.
449
10.10.1
1-VINYLNAPHTHALENE
.
449
10.10.2
TERT-BUTYL(3R,5S,6E')-7-[2-CYCLOPROPYL-4(4-FLUOROPHENYL)QUINOLIN-3-YL]
3,5-ISOPROPYLIDENEDIOXY-6-HEPTENOATE
.
450
10.10.3
4-FLUORO-4'
-METHOXY
1,1'
-BIPHENYL
.
450
10.10.4
3,4-DIFLUORO-4'-(TRANS-4-PROPYLCYCLOHEXYL)-L,L'-BIPHENYL
.
451
ABBREVIATIONS
.
451
REFERENCES
.
452
11
PALLADIUM-CATALYZED
COUPLING
REACTIONS
OF
PROPARGYLIC
COMPOUNDS
JIRO
TSUJI,
TADAKATSU
MANDAI
11.1
INTRODUCTION
.
455
11.2
CLASSIFICATION
OF
PALLADIUM-CATALYZED
REACTIONS
BASED
ON
MECHANISTIC
CONSIDERATIONS
.
455
CONTENTS
XXI
11.3
REACTIONS
VIA
INSERTION
INTO
THE
SP
2
CARBON
BOND
OF
ALLENYLPALLADIUM
INTERMEDIATES
(TYPE
I)
.
459
11.3.1
REACTIONS
OF
ALKENES:
FORMATION
OF
1,2,
4-ALKATRIENES
.
459
11.3.2
CARBONYLATION
.
459
11.3.2.1
REACTION
FEATURES
.
459
11.3.2.2
PREPARATION
OF
2,3-ALKADIENOATES
AND
THEIR
DERIVATIVES
BY
MONOCARBONYLATION
.
461
11.3.2.3
PREPARATION
OF
TRIESTERS
BY
DICARBONYLATION
.
463
11.3.2.4
DICARBONYLATION
OF
PROPARGYL
CHLORIDE
AND
ALCOHOLS
.
466
11.3.2.5
PREPARATION
OF
A-ALKENYLIDENE-Y-LACTONES
.
468
11.3.2.6
PREPARATION
OF
A-ALKENYLIDENE-^-LACTAMS
.
469
11.3.2.7
CARBONYLATION
IN
THE
PRESENCE
OF
ACTIVE
METHYLENE
AND
METHYNE
COMPOUNDS
.
469
11.3.2.8
DOMINO
CARBONYLATION
AND
DIELS-ALDER
REACTION
.
470
11.3.2.9
DOMINO
CARBONYLATION
AND
ENE
REACTION
.
471
11.3.2.10
PREPARATION
OF
CYCLOPENTENONECARBOXYLATES
.
473
11.4
REACTIONS
VIA
TRANSMETALLATION
OF
ALLENYLPALLADIUM
INTERMEDIATES
AND
RELATED
REACTIONS
(TYPE
II)
.
475
11.4.1
REACTIONS
OF
HARD
CARBON
NUCLEOPHILES
.
475
11.4.2
REACTION
OF
TERMINAL
ALKYNES:
FORMATION
OF
L,2-ALKADIEN-4-YNES
.
477
11.5
REACTIONS
VIA
ATTACK
BY
SOFT
CARBON
AND
OXO
NUCLEOPHILES
ON
THE CENTRAL
CARBON
OF
ALLENYLPALLADIUM
INTERMEDIATES
(TYPE
III)
.
479
11.5.1
REACTIONS
OF
SOFT
CARBON
NUCLEOPHILES
.
479
11.5.2
REACTION
OF
OXO
NUCLEOPHILES
.
484
11.6
EXPERIMENTAL
PROCEDURES
.
485
11.6.1
REACTION
OF
CARBONATE
WITH
ALKENES
.
485
11.6.2
DOMINO
CARBONYLATION
AND
DIELS-ALDER
REACTION
.
486
11.6.3
REACTION
WITH
ALKYNE
.
487
11.6.4
FURAN
FORMATION
BY
THE
REACTION
WITH
ACETOACETATE
.
487
ABBREVIATIONS
.
487
REFERENCE
.
489
AUTHOR
INDEX
.
491
SUBJECT
INDEX
.
495 |
| any_adam_object | 1 |
| author_GND | (DE-588)109354419 |
| building | Verbundindex |
| bvnumber | BV011638256 |
| classification_rvk | VK 5500 |
| classification_tum | CHE 624f CHE 622f CHE 330f |
| ctrlnum | (OCoLC)845024831 (DE-599)BVBBV011638256 |
| dewey-full | 547.1393 |
| dewey-hundreds | 500 - Natural sciences and mathematics |
| dewey-ones | 547 - Organic chemistry |
| dewey-raw | 547.1393 |
| dewey-search | 547.1393 |
| dewey-sort | 3547.1393 |
| dewey-tens | 540 - Chemistry and allied sciences |
| discipline | Chemie / Pharmazie Chemie |
| edition | Reprint. |
| format | Book |
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| id | DE-604.BV011638256 |
| illustrated | Illustrated |
| indexdate | 2024-08-17T00:53:36Z |
| institution | BVB |
| isbn | 352729421X |
| language | German |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-007843420 |
| oclc_num | 845024831 |
| open_access_boolean | |
| owner | DE-29T DE-703 DE-12 DE-20 DE-355 DE-BY-UBR DE-91G DE-BY-TUM DE-11 |
| owner_facet | DE-29T DE-703 DE-12 DE-20 DE-355 DE-BY-UBR DE-91G DE-BY-TUM DE-11 |
| physical | XXI, 517 S. graph. Darst. |
| publishDate | 1998 |
| publishDateSearch | 1998 |
| publishDateSort | 1998 |
| publisher | Wiley-VCH |
| record_format | marc |
| spelling | Metal catalyzed cross coupling reactions ed. by François Diederich ... Reprint. Weinheim [u.a.] Wiley-VCH 1998 XXI, 517 S. graph. Darst. txt rdacontent n rdamedia nc rdacarrier Literaturangaben. - 2. Aufl. mehrbändig Katalyse (DE-588)4029921-1 gnd rswk-swf Metallverbindungen (DE-588)4169640-2 gnd rswk-swf Kupplungsreaktion (DE-588)4166199-0 gnd rswk-swf Kupplungsreaktion (DE-588)4166199-0 s Katalyse (DE-588)4029921-1 s Metallverbindungen (DE-588)4169640-2 s DE-604 Diederich, François 1952-2020 Sonstige (DE-588)109354419 oth DNB Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=007843420&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Metal catalyzed cross coupling reactions Katalyse (DE-588)4029921-1 gnd Metallverbindungen (DE-588)4169640-2 gnd Kupplungsreaktion (DE-588)4166199-0 gnd |
| subject_GND | (DE-588)4029921-1 (DE-588)4169640-2 (DE-588)4166199-0 |
| title | Metal catalyzed cross coupling reactions |
| title_auth | Metal catalyzed cross coupling reactions |
| title_exact_search | Metal catalyzed cross coupling reactions |
| title_full | Metal catalyzed cross coupling reactions ed. by François Diederich ... |
| title_fullStr | Metal catalyzed cross coupling reactions ed. by François Diederich ... |
| title_full_unstemmed | Metal catalyzed cross coupling reactions ed. by François Diederich ... |
| title_short | Metal catalyzed cross coupling reactions |
| title_sort | metal catalyzed cross coupling reactions |
| topic | Katalyse (DE-588)4029921-1 gnd Metallverbindungen (DE-588)4169640-2 gnd Kupplungsreaktion (DE-588)4166199-0 gnd |
| topic_facet | Katalyse Metallverbindungen Kupplungsreaktion |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=007843420&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT diederichfrancois metalcatalyzedcrosscouplingreactions |