Rhodium catalysis in organic synthesis: methods and reactions
Gespeichert in:
| Weitere Verfasser: | |
|---|---|
| Format: | Buch |
| Sprache: | English |
| Veröffentlicht: |
Weinheim
Wiley-VCH
[2019]
|
| Schlagworte: | |
| Online-Zugang: | http://www.wiley-vch.de/publish/dt/books/ISBN978-3-527-34364-5/ Inhaltsverzeichnis |
| Beschreibung: | xv, 667 Seiten Illustrationen |
| ISBN: | 9783527343645 |
Internformat
MARC
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| 016 | 7 | |a 1165248123 |2 DE-101 | |
| 020 | |a 9783527343645 |c hbk. |9 978-3-527-34364-5 | ||
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| 245 | 1 | 0 | |a Rhodium catalysis in organic synthesis |b methods and reactions |c edited by Ken Tanaka |
| 264 | 1 | |a Weinheim |b Wiley-VCH |c [2019] | |
| 264 | 4 | |c © 2019 | |
| 300 | |a xv, 667 Seiten |b Illustrationen | ||
| 336 | |b txt |2 rdacontent | ||
| 337 | |b n |2 rdamedia | ||
| 338 | |b nc |2 rdacarrier | ||
| 650 | 0 | 7 | |a Rhodium |0 (DE-588)4178038-3 |2 gnd |9 rswk-swf |
| 650 | 0 | 7 | |a Rhodiumkomplexe |0 (DE-588)4314155-9 |2 gnd |9 rswk-swf |
| 650 | 0 | 7 | |a Katalyse |0 (DE-588)4029921-1 |2 gnd |9 rswk-swf |
| 650 | 0 | 7 | |a Organische Synthese |0 (DE-588)4075695-6 |2 gnd |9 rswk-swf |
| 653 | |a Chemie | ||
| 653 | |a Chemistry | ||
| 653 | |a Homogene Katalyse | ||
| 653 | |a Homogeneous Catalysis | ||
| 653 | |a Methods - Synthesis & Techniques | ||
| 653 | |a Organische Chemie / Methoden, Synthesen, Verfahren | ||
| 653 | |a Organische Synthese | ||
| 653 | |a Pharmaceutical & Medicinal Chemistry | ||
| 653 | |a Pharmazeutische u. Medizinische Chemie | ||
| 653 | |a Rhodium | ||
| 655 | 7 | |0 (DE-588)4143413-4 |a Aufsatzsammlung |2 gnd-content | |
| 689 | 0 | 0 | |a Rhodiumkomplexe |0 (DE-588)4314155-9 |D s |
| 689 | 0 | 1 | |a Organische Synthese |0 (DE-588)4075695-6 |D s |
| 689 | 0 | 2 | |a Katalyse |0 (DE-588)4029921-1 |D s |
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| 689 | 1 | 1 | |a Organische Synthese |0 (DE-588)4075695-6 |D s |
| 689 | 1 | 2 | |a Rhodium |0 (DE-588)4178038-3 |D s |
| 689 | 1 | |8 1\p |5 DE-604 | |
| 700 | 1 | |a Tanaka, Ken |d 1967- |0 (DE-588)118258070X |4 edt | |
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| 776 | 0 | 8 | |i Erscheint auch als |n Online-Ausgabe, ePDF |z 978-3-527-81187-8 |
| 776 | 0 | 8 | |i Erscheint auch als |n Online-Ausgabe, ePub |z 978-3-527-81189-2 |
| 776 | 0 | 8 | |i Erscheint auch als |n Online-Ausgabe, oBook |z 978-3-527-81190-8 |
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Datensatz im Suchindex
| _version_ | 1804179440411869184 |
|---|---|
| adam_text | CONTENTS
PREFACE
XV
PART
I
RHODIUM(L)
CATALYSIS
1
1
RHODIUM(L)-CATALYZED
ASYMMETRIC
HYDROGENATION
3
TSUNEO
IMAMOTO
1.1
INTRODUCTION
3
1.2
CHIRAL
PHOSPHORUS
LIGANDS
3
1.2.1
P-CHIROGENIC
BISPHOSPHINE
LIGANDS
4
1.2.1.1
ELECTRON-RICH
C
2
SYMMETRIC
LIGANDS
4
1.2.1.2
THREE-HINDERED
QUADRANT
LIGANDS
5
1.2.1.3
LIGANDS
BEARING
TWO
OR
THREE
ARYL
GROUPS
AT
THE
PHOSPHORUS
ATOM
5
1.2.2
DUPHOS,
BPE,
AND
ANALOGOUS
LIGANDS
6
1.2.3
FERROCENE-BASED
BISPHOSPHINE
LIGANDS
7
1.2.4
C
2
SYMMETRIC
TRIARYL-
OR
DIARYLPHOSPHINE
LIGANDS
WITH
AXIAL
CHIRALITY
9
1.2.5
PHOSPHINE-PHOSPHITE
AND
PHOSPHINE-PHOSPHORAMIDE
LIGANDS
9
1.2.6
OTHER
BIDENTATE
LIGANDS
9
1.2.7
MONODENTATE
PHOSPHORUS
LIGANDS
11
1.3
APPLICATION
OF
CHIRAL
PHOSPHORUS
LIGANDS
IN
RHODIUM-CATALYZED
ASYMMETRIC
HYDROGENATION
12
1.3.1
HYDROGENATION
OF
ALKENES
12
1.3.1.1
HYDROGENATION
OF
ENAMIDES
12
1.3.1.2
HYDROGENATION
OF
ENOL
ESTERS
18
1.3.1.3
HYDROGENATION
OF
A,(3-UNSATURATED
ACIDS,
ESTERS,
AND
RELATED
SUBSTRATES
19
1.3.1.4
HYDROGENATION
OF
OTHER
FUNCTIONALIZED
ALKENES
21
1.3.1.5
HYDROGENATION
OF
UNFUNCTIONALIZED
ALKENES
24
1.3.1.6
HYDROGENATION
OF
HETEROARENES
24
1.3.2
HYDROGENATION
OF
KETONES
25
1.3.3
HYDROGENATION
OF
IMINES,
OXIMES,
AND
HYDRAZONES
26
1.4
ENANTIOSELECTION
MECHANISM
OF
RHODIUM-CATALYZED
ASYMMETRIC
HYDROGENATION
27
1.5
CONCLUSION
28
REFERENCES
29
2
RHODIUM(L)-CATALYZED
HYDROBORATION
AND
DIBORATION
39
KOHEI
ENDO
2.1
2.2
2.2.1
2.2.2
2.2.3
2.3
2.3.1
2.3.2
2.4
INTRODUCTION
39
HYDROBORATION
OF
ALKENES
39
DEVELOPMENT
OF
CATALYST
SYSTEMS
39
ENANTIOSELECTIVE
REACTIONS
41
HYDROBORATION
OF
FUNCTIONALIZED
MOLECULES
44
DIBORATION
45
1,1
-DIBORATION
REACTIONS
45
1,2-DIBORATION
REACTIONS
45
CONCLUSION
46
REFERENCES
47
3
RHODIUM(L)-CATALYZED
HYDROFORMYLATION
AND
HYDROAMINATION
49
ZHIWEI
CHEN
AND
VY
M.
DONG
3.1
3.2
3.2.1
3.2.2
3.3
3.3.1
3.3.2
3.4
INTRODUCTION
49
RHODIUM(I)-CATALYZED
HYDROFORMYLATION
49
ASYMMETRIC
HYDROFORMYLATION
OF
CHALLENGING
SUBSTRATES
49
TRANSFER
HYDROFORMYLATION
50
RHODIUM(I)-CATALYZED
HYDROAMINATION
54
ASYMMETRIC
RHODIUM(I)-CATALYZED
HYDROAMINATION
54
ANTI-MARKOVNIKOV RHODIUM(I)-CATALYZED
HYDROAMINATION
56
CONCLUSION
59
REFERENCES
61
4
RHODIUM(L)-CATALYZED
HYDROACYLATION
63
MAITANE
FERNANDEZ
AND
MICHAEL
C.
WILLIS
4.1
4.2
4.2.1
4.2.2
4.3
4.3.1
4.3.2
4.3.3
4.3.4
4.4
INTRODUCTION
63
RHODIUM(I)-CATALYZED
INTRAMOLECULAR
HYDROACYLATION
63
SMALL
RING
SYNTHESIS:
FIVE-MEMBERED
RINGS
63
LARGER
RING
SYNTHESIS:
SIX-,
SEVEN-,
AND
EIGHT-MEMBERED
RINGS
66
RHODIUM(I)-CATALYZED
INTERMOLECULAR
HYDROACYLATION
68
TV-BASED
CHELATION
CONTROL
69
O-BASED
CHELATION
CONTROL
70
S-BASED
CHELATION
CONTROL
73
C=O
AS
A
DIRECTING GROUP
FOR
HYDROACYLATION
79
CONCLUSION
81
REFERENCES
81
5
RHODIUM(L)-CATALYZED
ASYMMETRIC
ADDITION
OF
ORGANOMETALLIC
REAGENTS
TO
UNSATURATED
COMPOUNDS
85
HSYUEH-LIANG
WU
AND
PING-YU
WU
5.1
INTRODUCTION
85
5.2
A,
P-UNSATURATED
KETONES
85
5.2.1
CHIRAL
PHOSPHORUS
LIGANDS
85
5.2.2
CHIRAL
DIENE
LIGANDS
89
5.2.3
CHIRAL
BIS-SULFOXIDE
LIGANDS
92
5.2.4
CHIRAL
HYBRID
LIGANDS
92
5.3
A,
P-UNSATURATED
ALDEHYDES
95
5.4
A,P-UNSATURATED
ESTERS
98
5.5
A,
P-UNSATURATED
AMIDES
102
5.6
A,P-UNSATURATED
PHOSPHONATES
70S
5.7
A,P-UNSATURATED
SULFONYL
COMPOUNDS
105
5.8
NITROOLEFIN
COMPOUNDS
707
5.9
ALKENYLHETEROARENE
AND
ALKENYLARENE
COMPOUNDS
111
5.10
CONCLUSION
111
REFERENCES
112
6
RHODIUM(L)-CATALYZED
ALLYLATION
WITH
ALKYNES
AND
ALLENES
117
ADRIAN
B.
PRITZIUS
AND
BERNHARD
BREIT
6.1
INTRODUCTION
117
6.2
RH(I)-CATALYZED
ADDITION
OF
O-NUCLEOPHILES
117
6.3
RH(I)-CATALYZED
ADDITION
OF
S-NUCLEOPHILES
123
6.4
RH(I)-CATALYZED
ADDITION
OF
N-NUCLEOPHILES
124
6.5
RH(I)-CATALYZED
ADDITION
OF
C-NUCLEOPHILES
127
6.6
APPLICATION
OF
RHODIUM-CATALYZED
ADDITION
IN
TOTAL
SYNTHESIS
127
6.7
CONCLUSION
129
REFERENCES
130
7
RHODIUM(L)-CATALYZED
REDUCTIVE
CARBON-CARBON
BOND
FORMATION
133
ADAM
D.
J.
CALOW
AND
JOHN
F.
BOWER
7.1
INTRODUCTION
133
7.2
HYDROFORMYLATION
133
7.2.1
DIRECTED
RH-CATALYZED
HYDROFORMYLATION
134
7.2.2
REVERSIBLY
BOUND
DIRECTING
GROUPS
IN
RH-CATALYZED
HYDROFORMYLATION
135
7.3
REDUCTIVE
C
*
C
BOND
FORMATION
BETWEEN
ELECTRON-DEFICIENT
ALKENES
AND
CARBONYLS
OR
IMINES
137
7.3.1
REDUCTIVE
ALDOL
REACTIONS
137
7.3.2
REDUCTIVE
MANNICH
REACTIONS
142
7.4
REDUCTIVE
C
*
C
BOND
FORMATION
BETWEEN
LESS
POLARIZED
CARBON-BASED
JR-UNSATURATED
SYSTEMS
AND
CARBONYLS,
IMINES,
OR
ANHYDRIDES
144
7.4.1
REDUCTIVE
C
*
C
BOND
FORMATIONS
BETWEEN
ALKENES
AND
CARBONYLS,
IMINES,
OR
ANHYDRIDES
144
7.4.2
REDUCTIVE
C
*
C
BOND
FORMATIONS
BETWEEN
ALKYNES
AND
CARBONYLS
OR
IMINES
146
7.4.3
MISCELLANEOUS
PROCESSES
150
7.5
REDUCTIVE
C
*C
BOND
FORMATION
BETWEEN
CARBON-BASED
JC-UNSATURATED
SYSTEMS
151
7.5.1
C
*
C
BOND-FORMING
REACTIONS
BETWEEN
ALKENES
AND
ALKYNES
151
7.5.2
C
*
C
BOND-FORMING
REACTIONS
BETWEEN
ALKYNES
AND
ALKYNES
154
7.6
CONCLUSIONS
156
REFERENCES
156
8
RHODIUM(L)-CATALYZED
[2+2+1]
AND
[4+1]
CYCLOADDITIONS
161
TSUMORU
MORIMOTO
8.1
INTRODUCTION
161
8.2
[2+2+1]
CYCLOADDITION
161
8.2.1
[2+2+1]
CYCLOADDITION
OF
AN
ALKYNE,
AN
ALKENE,
AND
CO
(PAUSON-KHAND-TYPE
REACTION)
161
8.2.1.1
PAUSON-KHAND-TYPE
REACTION
USING
ALDEHYDES
AS
A
CL
COMPONENT
162
8.2.1.2
PAUSON-KHAND-TYPE
REACTION
USING
FORMATES
AS
A
CL
COMPONENT
171
8.2.1.3
PAUSON-KHAND-TYPE
REACTION
USING
OXALIC
ACID
AS
A
CL
COMPONENT
171
8.2.1.4
PAUSON-KHAND-TYPE
REACTION
USING
SUPPORTED
CARBON
MONOXIDE
172
8.2.2
[2+2+1]
CYCLOADDITION
OF
TWO
ALKYNES
AND
CO
172
8.2.3
CARBONYLATIVE
[2+2+1]
CYCLOADDITION
INCLUDING
/ZETERO-MULTIPLE
BONDS
174
8.3
[4+1]
CYCLOADDITION
176
8.3.1
CYCLOADDITION
OF
ALL
CARBON
4JR-CONJUGATED
SYSTEMS
WITH
CO
176
8.3.2
CYCLOADDITION
OF
4RC-CONJUGATED
SYSTEMS
INCLUDING
NITROGEN
ATOM
178
8.4
CONCLUSION
179
REFERENCES
179
9
RHODIUM(L)-CATALYZED
[2+2+2]
AND
[4+2]
CYCLOADDITIONS
183
YU
SHIBATA
AND
KEN
TANAKA
9.1
INTRODUCTION
183
9.2
[2+2+2]
CYCLOADDITION
183
9.2.1
[2+2+2]
CYCLOADDITION
OF
ALKYNES
184
9.2.2
[2+2+2]
CYCLOADDITION
OF
ALKYNES
WITH
NITRILES
199
9.2.3
[2+2+2]
CYCLOADDITION
OF
ALKYNES
WITH
HETEROCUMULENES
200
9.2.4
[2+2+2]
CYCLOADDITION
OF
ALKYNES
WITH
ALKENES
207
9.2.5
[2+2+2]
CYCLOADDITION
OF
ALKYNES
WITH
CARBONYL
COMPOUNDS
AND
IMINES
211
9.3
[4+2]
CYCLOADDITION
214
9.3.1
[4+2]
CYCLOADDITION
OF
ALKYNES
WITH
1,3-DIENES 215
9.3.2
[4+2]
CYCLOADDITION
VIA
C
*
H
BOND
CLEAVAGE
218
9.4
CONCLUSION
222
REFERENCES
225
10
RHODIUM(L)-CATALYZED
CYCLOADDITIONS
INVOLVING
VINYLCYDOPROPANES
AND
THEIR
DERIVATIVES
229
XING
FAN,
CHENG-HANG
LIU,
AND
ZHI-XIANG
YU
10.1
INTRODUCTION
229
10.2
VCP
ISOMERIZATION
CATALYZED
BY
RH(I)
230
10.3
CYCLOADDITION
REACTIONS
USING
VCPS
5C
SYNTHON
231
10.3.1
[5+1]
CYCLOADDITIONS
OF
VCPS
AND
CO
231
10.3.2
[5+1]
CYCLOADDITION
REACTIONS
OF
VCP
DERIVATIVES
AND
CO
233
10.3.3
INTERMOLECULAR
[5+2]
CYCLOADDITION
REACTIONS
237
10.3.4
INTRAMOLECULAR
[5+2]
CYCLOADDITION
REACTIONS
239
10.3.5
[5+2]
CYCLOADDITION
REACTIONS
OF
VCP
DERIVATIVES
WITH
2
JT
COMPONENTS
245
10.3.6
[5+2+1]
AND
[5+1+2+1]
CYCLOADDITION
REACTIONS
251
10.4
CYCLOADDITION
REACTIONS
USING
VCPS
3C
SYNTHON
255
10.4.1
[3+2]
CYCLOADDITION
REACTIONS
OF
VCPS
255
10.4.2
[3+2]
CYCLOADDITION
REACTIONS
OF
VCP
DERIVATIVES
AND
2JR-COMPONENTS
261
10.4.3
[3+2+1]
CYCLOADDITION
REACTIONS
262
10.4.4
[3+4]
AND
[3+3]
CYCLOADDITION
REACTIONS
OF
VINYLAZIRIDINES
264
10.5
MISCELLANEOUS
CYCLOADDITION
266
10.5.1
[7+1]
CYCLOADDITION
OF
BUTA-L,3-DIENYLCYCLOPROPANES
266
10.5.2
INTRAMOLECULAR
REACTIONS
OF
ACPS
AND
2N-8YNTHON
266
10.5.3
INTRAMOLECULAR
HYDROACYLATION
OF
VCPS
268
10.6
CONCLUSION
270
ACKNOWLEDGMENTS
270
REFERENCES
271
11
RHODIUM(L)-CATALYZED
REACTIONS
VIA
CARBON-HYDROGEN
BOND
CLEAVAGE
277
TAKANORI
SHIBATA
11.1
INTRODUCTION
277
11.2
C-H
ARYLATION
277
11.3
C-H
ALKYLATION
279
11.3.1
DIRECTED
C-H
ALKYLATION
BY
ALKENES
279
11.3.2
UNDIRECTED
C-H
ALKYLATION
BY
ALKENE
281
11.4
C-H
ALKENYLATION
283
11.5
TANDEM
REACTION
INITIATED
BY
C-H
ACTIVATION
285
11.6
C-H
BORYLATION
287
11.7
UNDIRECTED
DEHYDROGENATIVE
C-H/SI-H
COUPLING
290
11.8
CONCLUSION
295
REFERENCES
295
12
RHODIUM(L)-CATALYZED
REACTIONS
VIA
CARBON-CARBON
BOND
CLEAVAGE
299
MASAHIRO
MURAKAMI
AND
NAOKI
ISHIDA
12.1
INTRODUCTION
299
12.2
12.3
12.4
12.5
12.6
12.7
REACTIONS
OF
CYCLOPROPANES
AND
CYCLOBUTANES
299
REACTIONS
VIA
CLEAVAGE
OF
C(CARBONYL)
*
C
BONDS
310
REACTIONS
VIA
DIRECTING
GROUP-ASSISTED
C
*
C
BOND
CLEAVAGE
315
REACTIONS
OF
ALCOHOLS
VIA
C
*
C
BOND
CLEAVAGE
323
REACTIONS
VIA
CLEAVAGE
OF
C
*
CN
BOND
330
REACTIONS
VIA
DECARBONYLATION
OF
ALDEHYDES
AND
CARBOXYLIC
ACID
DERIVATIVES
332
12.8
CONCLUSION
333
REFERENCES
334
PART
II
RHODIUM(LL)
CATALYSIS
341
13
RHODIUM(LL)
TETRACARBOXYLATE-CATALYZED
ENANTIOSELECTIVE
C-H
FUNCTIONALIZATION
REACTIONS
343
SIDNEY
M.
WILKERSON-HILL
AND
HUW
M.
L
DAVIES
13.1
13.2
13.3
INTRODUCTION
343
MECHANISTIC
INSIGHTS
AND
GENERAL
CONSIDERATIONS
344
DEVELOPMENT
OF
RH
2
(S-DOSP)
4
AS
A
CHIRAL
CATALYST
FOR
C-H
FUNCTIONALIZATION
347
13.4
13.5
COMBINED
C-H
FUNCTIONALIZATION/COPE
REARRANGEMENT
350
PHTHALIMIDO
AMINO
ACID-DERIVED
CATALYSTS
FOR
INTRAMOLECULAR
C-H
FUNCTIONALIZATION
353
13.6
DEVELOPMENT
OF
TRIARYLCYCLOPROPANE
CARBOXYLATE
RH(II)
COMPLEXES
FOR
CATALYST-CONTROLLED
SITE-SELECTIVE
C-H
FUNCTIONALIZATION
359
13.7
EMERGING
CHIRAL
DIRHODIUM
CATALYST
FOR
ENANTIOSELECTIVE
C-H
FUNCTIONALIZATION
364
13.8
13.9
NEW
PARADIGMS
IN
THE
LOGIC
OF
CHEMICAL
SYNTHESIS
365
CONCLUSION
368
ACKNOWLEDGMENTS
369
REFERENCES
369
14
RHODIUM(LL)-CATALYZED
NITROGEN-ATOM
TRANSFER
FOR
OXIDATION
OF
ALIPHATIC
C
*
H
BONDS
373
TOM
G.
DRIVER
14.1
14.2
14.2.1
INTRODUCTION
373
MECHANISM-INSPIRED
DEVELOPMENT
OF
NEW
RH
2
(II)
CATALYSTS
374
MECHANISM
OF
INTRAMOLECULAR
RH
2
(II)-CATALYZED
C
*
H
BOND
AMINATION
374
14.2.2
TETRADENTATE
CARBOXYLATE
LIGANDS
FOR
BIMETALLIC
RHODIUM(II)
COMPLEXES
375
14.2.3
14.3
DESIGN,
SYNTHESIS,
AND
PERFORMANCE
OF
RH
2
II
IN
COMPLEXES
381
THE
DEVELOPMENT
OF
NEW
INTRAMOLECULAR
RH
2
(II)-CATALYZED
SP
3
-C
*
H
BOND
AMINATION
383
14.3.1
14.3.2
C
*
H
BOND
AMINATION
OF
ETHEREAL
BONDS
383
THE
USE
OF
RH
2
(II)-CATALYZED
C
*
H
BOND
AMINATION
TO
CREATE
GLYCANS
AND
GLYCOSIDES
385
14.3.3
C
*
H
BOND
AMINATION
OF
MIDA
BORONATES
386
14.3.4
FORMATION
OF
MEDIUM-RING
N-
HETEROCYCLES
THROUGH
C
*
H
BOND
AMINATION
387
14.3.5
SYNTHESIS
OF
SPIROAMINAL
SCAFFOLDS
387
14.3.6
EXPANDING
THE
SCOPE
OF
C
*
H
BOND
AMINATION
WITH
NEW
NH
2
-BASED
N-ATOM
PRECURSORS
389
14.3.7
N
-TOSYLCARBAMATE
N-ATOM
PRECURSORS
IN
RH
2
(II)-CATALYZED
C
*
H
BOND
AMINATION
REACTIONS
394
14.3.8
ARYL
AZIDE
N-ATOM
PRECURSORS
IN
RH
2
(II)-CATALYZED
SP
3
-C
*
-H
BOND
AMINATION
REACTIONS
398
14.4
INTERMOLECULAR
RH
2
(II)-CATALYZED
SP
3
-C
*
H
BOND
AMINATION
USING
AN
IODINE(III)
OXIDANT TO
GENERATE
THE
NITRENE
400
14.4.1
INTERMOLECULAR
C
*
H
BOND
AMINATION
OF
ACTIVATED
C
*
H
BONDS
400
14.5
NON-OXIDATIVELY
GENERATED
NITRENES
IN
INTERMOLECULAR
RH
2
(II)-CATALYZED
SP
3
-C
*
H
BOND
AMINATION
411
14.5.1
N
-TOSYLCARBAMATES
AS
THE NITROGEN-ATOM
PRECURSOR
IN
INTERMOLECULAR
SP
3
-C
*
H
BOND
AMINATION
PROCESSES
411
14.5.2
AZIDES
AS
THE
NITROGEN-ATOM
PRECURSOR
IN
INTERMOLECULAR
SP
3
-C
*
H
BOND
AMINATION
REACTIONS
414
14.6
DIASTEREOSELECTIVE
RH
2
(II)-CATALYZED
SP
3
-C
*
H
BOND
AMINATION
USING
CHIRAL,
NON-RACEMIC
NITROGEN-ATOM
PRECURSORS
416
14.6.1
INTERMOLECULAR
DIASTEREOSELECTIVE
C
*
H
BOND
AMINATION
USING
SULFONIMIDAMIDES
416
14.6.2
INTERMOLECULAR
DIASTEREOSELECTIVE
C
*
H
BOND
AMINATION
USING
TV-TOSYLCARBAMATES
422
14.7
ENANTIOSELECTIVE
RH
2
(II)-CATALYZED
SP
3
-C
*
H
BOND
AMINATION
422
14.7.1
INTRAMOLECULAR
ASYMMETRIC
C
*
H
BOND
AMINATION
422
14.8
CONCLUSION
429
REFERENCES
430
15
RHODIUM(LL)-CATALYZED
CYCLOPROPANATION
433
VINCENT
N.G.
LINDSAY
15.1
INTRODUCTION
433
15.1.1
MECHANISTIC
CONSIDERATIONS
434
15.2
INTERMOLECULAR
CYCLOPROPANATION
OF
ALKENES
436
15.2.1
VIA
RHODIUM(II)
CARBENES
BEARING
ONE
ELECTRON-WITHDRAWING GROUP
(ACCEPTOR
CARBENES)
438
15.2.2
VIA
RHODIUM(II)
CARBENES
BEARING
ONE
ELECTRON-WITHDRAWING GROUP
AND
ONE
ELECTRON-DONATING
GROUP
(DONOR-ACCEPTOR
CARBENES)
440
15.2.3
VIA
RHODIUM(II)
CARBENES
BEARING
TWO
ELECTRON-WITHDRAWING
GROUPS
(ACCEPTOR-ACCEPTOR
CARBENES)
441
15.3
INTRAMOLECULAR
CYCLOPROPANATION
OF
ALKENES
443
15.4
CYCLOPROPANATION
OF
POORLY
NUCLEOPHILIC
^-SYSTEMS:
ALKYNES,
ARENES,
AND
ALLENES
AS
SUBSTRATES
444
15.5
CONCLUSION
445
REFERENCES
445
16
REACTIONS
OF
A-LMINO
RHODIUM(LL)
CARBENE
COMPLEXES
GENERATED
FROM
N-
SULFONYL-1
,2,3-7
RIAZOLES
449
TOMOYA
MIURA
AND
MASAHIRO
MURAKAMI
16.1
INTRODUCTION
449
16.2
SYNTHESIS
OF
TV-SULFONYL-
1,2,
3-TRIAZOLES
451
16.3
REACTIONS
OF
CARBON
NUCLEOPHILES
WITH
A-IMINO
RHODIUM(II)
CARBENE
COMPLEXES
451
16.4
REACTIONS
OF
OXYGEN
AND
SULFUR
NUCLEOPHILES
WITH
A-IMINO
RHODIUM(II)
CARBENE
COMPLEXES
458
16.5
REACTIONS
OF
NITROGEN
NUCLEOPHILES
WITH
A-IMINO
RHODIUM(II)
CARBENE
COMPLEXES
464
16.6
CONCLUSION
466
REFERENCES
467
17
RHODIUM(LL)-CATALYZED
1,3-
AND
1
,5-DIPOLAR
CYCLOADDITION
471
NIRUPAM
DE,
DONGUK
KO,
AND
EUN
JEONG
YOO
17.1
INTRODUCTION
471
17.2
1,3-DIPOLAR
CYCLOADDITIONS
OF
CARBONYL
YLIDES
471
17.2.1
[3+2]
CYCLOADDITIONS
OF
CARBONYL
YLIDES
AND
DIPOLAROPHILES
471
17.2.2
CHEMOSELECTIVE
[3+2]
CYCLOADDITIONS
OF
CARBONYL
YLIDES
475
17.2.3
APPLICATIONS
TO
NATURAL
PRODUCT
SYNTHESIS
476
17.3
1,3-DIPOLAR
CYCLOADDITIONS
OF
AZOMETHINE
YLIDES
478
17.4
1,3-DIPOLAR
CYCLOADDITIONS
OF
ENOLDIAZO
COMPOUNDS
479
17.5
1,5-DIPOLAR
CYCLOADDITIONS
OF
PYRIDINIUM
ZWITTERIONS
482
17.6
CONCLUSION
484
REFERENCES
484
PART
III
RHODIUM(LLL)
CATALYSIS
487
18
RHODIUM(LLL)-CATALYZED
ANNULATIVE
CARBON-HYDROGEN
BOND
FUNCTIONALIZATION
489
TETSUYA
SATOH
AND
MASAHIRO
MIURA
18.1
INTRODUCTION
489
18.2
TYPE
A
ANNULATION
490
18.2.1
ANNULATION
UTILIZING
OXYGEN-CONTAINING
DIRECTING
GROUP
490
18.2.2
ANNULATION
UTILIZING
NITROGEN-CONTAINING
DIRECTING GROUP
492
18.2.3
ANNULATION
UTILIZING
SULFUR-CONTAINING DIRECTING
GROUP
504
18.2.4
ANNULATION
UTILIZING
PHOSPHORUS-CONTAINING
DIRECTING
GROUP
506
18.3
TYPE
B
ANNULATION
508
18.4
TYPE
C
ANNULATION
510
18.5
TYPE
D
CYCLIZATION
515
18.6
CONCLUSION
516
REFERENCES
517
19
529
540
19.4.5
20
20.1
19.4.3.1
19.4.3.2
19.4.3.3
19.4.4
577
579
564
569
19.4.2
19.4.3
552
555
558
19.5
19.5.1
19.5.2
19.6
19.6.1
19.6.2
19.7
19.8
19.9
19.9.1
19.9.2
19.10
19.11
19.12
STERICALLY
AND
ELECTRONICALLY
TUNED
CP
LIGANDS
FOR
RHODIUM(LLL)-CATALYZED
CARBON-HYDROGEN
BOND
FUNCTIONALIZATION
593
FEDOR
ROMANOV-MICHAIIIDIS,
ERIKJ.T.
PHIPPS
,
AND
TOMISLAV
ROVIS
INTRODUCTION
593
RHODIUM(LLL)-CATALYZED
NON-ANNULATIVE
CARBON-HYDROGEN
BOND
FUNCTIONALIZATION
521
FANG
XIE
AND
XINGWEI
LI
INTRODUCTION
521
ALKENYLATION
AND
ARYLATION
522
RH(III)-CATALYZED
NON-ANNULATIVE
C
*
H
ALKENYLATION
522
OXIDATIVE
DEHYDROGENATIVE
ALKENYLATION
REACTIONS
522
REDOX-NEUTRAL
ALKENYLATION
WITH
INTERNAL
OXIDIZING
ABILITY
523
ALKENYLATIONS
FROM
ALKYNES
525
RH(III)-CATALYZED
NON-ANNULATIVE
C
*
H
ARYLATION
529
NON-ANNULATIVE
OXIDATIVE
DEHYDROGENATIVE
ARYLATION
OTHER
TYPES
OF
C-H
ARYLATION
533
ALKYNYLATION
540
RH(III)-CATALYZED
NON-ANNULATIVE
C
*
H
ALKYNYLATION
ALKYLATION
541
RH(III)-CATALYZED
NON-ANNULATIVE
C
*
H
COUPLINGS
WITH
DIAZO
COMPOUNDS
541
RH(III)-CATALYZED
NON-ANNULATIVE
ALLYLATIONS
543
RH(III)-CATALYZED
NON-ANNULATIVE
ALKYLATIONS
THROUGH
ADDITION
OF
C
*
H
BOND
TO
C=X
(X
=
C,
O,
N)
BONDS
552
ADDITION
OF
C
*
H
BOND
TO
C=C
BOND
ADDITION
OF
C
*
H
BOND
TO
C=O
BOND
ADDITION
OF
C
*
H
BOND
TO
C=N
BOND
RH(III)-CATALYZED
NON-ANNULATIVE
ALKYLATIONS
THROUGH
OPENING
STRAINED
RINGS
560
RH(III)-CATALYZED
NON-ANNULATIVE
ALKYLATIONS
THROUGH
TRANSMETALATION
563
C
*
N
BOND
FORMATION
564
RH(III)-CATALYZED
NON-ANNULATIVE
AMINATIONS
RH(III)-CATALYZED
NON-ANNULATIVE
AMIDATIONS
INTRODUCTION
OF
C=O
BOND
577
RH(III)-CATALYZED
NON-ANNULATIVE
ACYLATIONS
RH(III)-CATALYZED
NON-ANNULATIVE
AMIDATIONS
CYANATION
579
C
*
O
BOND
FORMATION
580
C
*
X
BOND
FORMATION
581
NON-ANNULATIVE
HALOGENATION
OF
ARENES
581
C
*
H
HYPERIODINATION
OF
ARENES
583
NON-ANNULATIVE
THIOLATION
OF
ARENES
585
C
*
SE
BOND
FORMATION
585
CONCLUSION
586
REFERENCES
587
19.1
19.2
19.2.1
19.2.1.1
19.2.1.2
19.2.1.3
19.2.2
19.2.2.1
19.2.2.2
19.3
19.3.1
19.4
19.4.1
20.2
QUANTITATIVE
MODELS
FOR
STERIC
AND
ELECTRONIC
PARAMETERIZATION OF
CP
LIGANDS
ON
RHODIUM(III)
594
20.3
STERICALLY
TUNED
CP
LIGANDS
598
20.3.1
EARLIER
RESULTS
598
20.3.2
SYNTHESIS
OF
ISOQUINOLONES,
PYRIDONES,
AND
DERIVATIVES
599
20.3.3
SYNTHESIS
OF
PYRIDINES
607
20.3.4
CYCLOPROPANATION
AND
CARBOAMINATION
REACTIONS
607
20.4
ELECTRONICALLY
TUNED
CP
LIGANDS
612
20.4.1
SYNTHESIS
OF
PYRIDINES
AND
DERIVATIVES
612
20.4.2
TANAKA
*
S
ETHOXYCARBONYLSUBSTITUTED
CYCLOPENTADIENYL
LIGAND
(CP
E
)
615
20.5
CONCLUSION
626
REFERENCES
626
21
CHIRAL
CP
LIGANDS
FOR
RHODIUM(LLL)-CATALYZED
ASYMMETRIC
CARBON-HYDROGEN
BOND
FUNCTIONALIZATION
629
CHRISTOPHER
G.
NEWTON
AND
NICOLAI
CRAMER
21.1
INTRODUCTION
629
21.2
SEMINAL
WORK
629
21.3
THE
LIGANDS
630
21.3.1
DEVELOPMENT
630
21.3.2
ESTABLISHED
FAMILIES
631
21.3.3
COMPLICATION
METHODS
633
21.4
APPLICATIONS
634
21.4.1
INTRODUCTION
634
21.4.2
HYDROXAMATE
DIRECTING GROUPS
634
21.4.3
PYRIDYL
DIRECTING
GROUPS
638
21.4.4
HYDROXY
DIRECTING
GROUPS
639
21.4.5
OTHER
DIRECTING
GROUPS
641
21.5
CONCLUSION
642
REFERENCES
642
INDEX
645
|
| any_adam_object | 1 |
| author2 | Tanaka, Ken 1967- |
| author2_role | edt |
| author2_variant | k t kt |
| author_GND | (DE-588)118258070X |
| author_facet | Tanaka, Ken 1967- |
| building | Verbundindex |
| bvnumber | BV045503312 |
| classification_rvk | VK 5550 |
| ctrlnum | (OCoLC)1091663350 (DE-599)DNB1165248123 |
| discipline | Chemie / Pharmazie |
| format | Book |
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| genre | (DE-588)4143413-4 Aufsatzsammlung gnd-content |
| genre_facet | Aufsatzsammlung |
| id | DE-604.BV045503312 |
| illustrated | Illustrated |
| indexdate | 2024-07-10T08:19:54Z |
| institution | BVB |
| institution_GND | (DE-588)16179388-5 |
| isbn | 9783527343645 |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-030887977 |
| oclc_num | 1091663350 |
| open_access_boolean | |
| owner | DE-29T DE-83 DE-11 |
| owner_facet | DE-29T DE-83 DE-11 |
| physical | xv, 667 Seiten Illustrationen |
| publishDate | 2019 |
| publishDateSearch | 2019 |
| publishDateSort | 2019 |
| publisher | Wiley-VCH |
| record_format | marc |
| spelling | Rhodium catalysis in organic synthesis methods and reactions edited by Ken Tanaka Weinheim Wiley-VCH [2019] © 2019 xv, 667 Seiten Illustrationen txt rdacontent n rdamedia nc rdacarrier Rhodium (DE-588)4178038-3 gnd rswk-swf Rhodiumkomplexe (DE-588)4314155-9 gnd rswk-swf Katalyse (DE-588)4029921-1 gnd rswk-swf Organische Synthese (DE-588)4075695-6 gnd rswk-swf Chemie Chemistry Homogene Katalyse Homogeneous Catalysis Methods - Synthesis & Techniques Organische Chemie / Methoden, Synthesen, Verfahren Organische Synthese Pharmaceutical & Medicinal Chemistry Pharmazeutische u. Medizinische Chemie Rhodium (DE-588)4143413-4 Aufsatzsammlung gnd-content Rhodiumkomplexe (DE-588)4314155-9 s Organische Synthese (DE-588)4075695-6 s Katalyse (DE-588)4029921-1 s DE-604 Rhodium (DE-588)4178038-3 s 1\p DE-604 Tanaka, Ken 1967- (DE-588)118258070X edt Wiley-VCH (DE-588)16179388-5 pbl Erscheint auch als Online-Ausgabe, ePDF 978-3-527-81187-8 Erscheint auch als Online-Ausgabe, ePub 978-3-527-81189-2 Erscheint auch als Online-Ausgabe, oBook 978-3-527-81190-8 X:MVB http://www.wiley-vch.de/publish/dt/books/ISBN978-3-527-34364-5/ DNB Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=030887977&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis 1\p cgwrk 20201028 DE-101 https://d-nb.info/provenance/plan#cgwrk |
| spellingShingle | Rhodium catalysis in organic synthesis methods and reactions Rhodium (DE-588)4178038-3 gnd Rhodiumkomplexe (DE-588)4314155-9 gnd Katalyse (DE-588)4029921-1 gnd Organische Synthese (DE-588)4075695-6 gnd |
| subject_GND | (DE-588)4178038-3 (DE-588)4314155-9 (DE-588)4029921-1 (DE-588)4075695-6 (DE-588)4143413-4 |
| title | Rhodium catalysis in organic synthesis methods and reactions |
| title_auth | Rhodium catalysis in organic synthesis methods and reactions |
| title_exact_search | Rhodium catalysis in organic synthesis methods and reactions |
| title_full | Rhodium catalysis in organic synthesis methods and reactions edited by Ken Tanaka |
| title_fullStr | Rhodium catalysis in organic synthesis methods and reactions edited by Ken Tanaka |
| title_full_unstemmed | Rhodium catalysis in organic synthesis methods and reactions edited by Ken Tanaka |
| title_short | Rhodium catalysis in organic synthesis |
| title_sort | rhodium catalysis in organic synthesis methods and reactions |
| title_sub | methods and reactions |
| topic | Rhodium (DE-588)4178038-3 gnd Rhodiumkomplexe (DE-588)4314155-9 gnd Katalyse (DE-588)4029921-1 gnd Organische Synthese (DE-588)4075695-6 gnd |
| topic_facet | Rhodium Rhodiumkomplexe Katalyse Organische Synthese Aufsatzsammlung |
| url | http://www.wiley-vch.de/publish/dt/books/ISBN978-3-527-34364-5/ http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=030887977&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT tanakaken rhodiumcatalysisinorganicsynthesismethodsandreactions AT wileyvch rhodiumcatalysisinorganicsynthesismethodsandreactions |