Transition metal-catalyzed heterocycle synthesis via C-H activation:
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| Beschreibung: | XXXI, 562 Seiten Illustrationen (teilweise farbig) |
| ISBN: | 9783527338887 9783527691920 |
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| 245 | 1 | 0 | |a Transition metal-catalyzed heterocycle synthesis via C-H activation |c edited by Xiao-Feng Wu |
| 264 | 1 | |a Weinheim |b Wiley-VCH Verlag GmbH & Co. KGaA |c [2016] | |
| 264 | 4 | |c © 2016 | |
| 300 | |a XXXI, 562 Seiten |b Illustrationen (teilweise farbig) | ||
| 336 | |b txt |2 rdacontent | ||
| 337 | |b n |2 rdamedia | ||
| 338 | |b nc |2 rdacarrier | ||
| 650 | 0 | 7 | |a Katalyse |0 (DE-588)4029921-1 |2 gnd |9 rswk-swf |
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| 653 | |a Catalysis | ||
| 653 | |a Chemie | ||
| 653 | |a Chemistry | ||
| 653 | |a Katalyse | ||
| 653 | |a Metallorganische Verbindungen | ||
| 653 | |a Nachhaltige u. Grüne Chemie | ||
| 653 | |a Nachhaltigkeit | ||
| 653 | |a Organometallchemie | ||
| 653 | |a Organometallic Chemistry | ||
| 653 | |a Pharmaceutical & Medicinal Chemistry | ||
| 653 | |a Pharmazeutische u. Medizinische Chemie | ||
| 653 | |a Sustainable Chemistry & Green Chemistry | ||
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| 856 | 4 | 2 | |m X:MVB |q text/html |u http://deposit.dnb.de/cgi-bin/dokserv?id=5327578&prov=M&dok_var=1&dok_ext=htm |3 Inhaltstext |
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CONTENTS
UST OF CONTRIBUTORS XXI
FOREWORD 1 XXVII
FOREWORD 2 XXIX
PREFACE XXXI
YY COMPUTATIONAL STUDIES OF HETEROATOM-ASSISTED C-H ACTIVATION
AT RU, RH, LR, AND PD AS A BASIS FOR HETEROCYCLE SYNTHESIS AND
DERIVATIZATION 1
KEVINJ. T. CARR
YY
STUARTA. MACGREGOR, AND CLAIRE L MCMULLIN
1.1 INTRODUCTION 1
1.2 PALLADIUM 2
1.2.1 INTRAMOLECULAR HETEROATOM-ASSISTED C-H ACTIVATION 2
1.2.1.1 EARLY COMPUTATIONAL STUDIES 2
1.2.1.2 THE ROLE OF THE BASE, SOLVENT, AND ADDITIVES ON PD.MEDIATED
INTRAMOLECULAR C-H ACTIVATION 5
1.2.1.3 INTRAMOLECULAR C-H ACTIVATION OF HETEROCYCLIC SUBSTRATES 9
1.2.2 INTERMOLECULAR C-H ACTIVATION
11
1.2.2.1 EARLY COMPUTATIONAL STUDIES "
1.2.2.2 DIRECT FUNCTIONALIZATION VIA C-H ACTIVATION OF HETEROCYCLIC
SUBSTRATES 15
1.3 RUTHENIUM, RHODIUM, AND IRIDIUM 22
1.3.1 INTRAMOLECULAR HETEROATOM.ASSISTED C-H ACTIVATION 22
1.3.2 INTERMOLECULAR C-H ACTIVATION 25
1.3.3 C-H ACTIVATION AND FUNCTIONALIZATION 27
1.3.3.1 HETEROCYCLE FORMATION WITH INTERNAL OXIDANTS 28
1.3.3.2 HETEROCYCLE FORMATION WITHOUT INTERNAL OXIDANTS 34
1.3.4 ALKENYLATION AND AMINATION 38
1.4 CONCLUSIONS 40
ACKNOWLEDGMENTS 41
REFERENCES 41
2
2.1
2.2
2.3
2.3.1
2.3.2
94
2.5
3
3.1
3.2
3.2.1
3.2.2
3.2.3
3.2.4
3.3
3.3.1
3.3.2
3.4
4
4.1
4 9
4.2.1
4.2.2
4.2.3
4
9
4
4.3
4.3.1
4.3.2
4.3.3
4.4
4.4.1
4
4
9
PD-CATALYZED SYNTHESIS OF NITROGEN-CONTAINING HETEROCYCLES 45
LIXIN LI, XIAOLEIJI, AND HANMING HUANG
INTRODUCTION 45
GENERAL CONSIDERATION ON PALLADIUM CHEMISTRY 45
HETEROCYCLE SYNTHESIS VIA C(SP3)-H ACTIVATION 46
HETEROCYCLE SYNTHESIS VIA ACTIVATED C(SP3)-H BONDS 47
HETEROCYCLE SYNTHESIS VIA UNACTIVATED C(SP3)-H BONDS 49
HETEROCYCLES VIA C(SP2)-H ACTIVATION 55
CONCLUSIONS 61
REFERENCES 62
PD-CATALYZED SYNTHESIS OF OXYGEN-CONTAINING HETEROCYCLES 65
YUDONG YANG ONDJINGSONG YOU
INTRODUCTION 65
PALLADIUM-CATALYZED C-.H ACTIVATION/C-C FORMATION TO CONSTRUCT
OXACYCLES 66
PALLADIUM-CATALYZED C-H BOND ARYLATION 67
PALLADIUM-CATALYZED C-H OLEFINATION 69
PALLADIUM-CATALYZED C-H ALKYLATION 75
PALLADIUM-CATALYZED C-H CARBONYLATION AND CARBOXYLATION 76
PALLADIUM-CATALYZED C-H ACTIVATION/C-O FORMATION TO CONSTRUCT
OXACYCLES 80
PALLADIUM-CATALYZED C
-
O BOND FORMATION VIA C(SP2)-H
ACTIVATION 81
PALLADIUM-CATALYZED C
-
O BOND FORMATION VIA ALLYLIC C-H
ACTIVATION 84
CONCLUSIONS 86
REFERENCES 87
PD-CATALYZED SYNTHESIS OF OTHER HETEROATOM.CONTAINING
HETEROCYCLES 91
ZHANXIONG LIU AND YUHONG ZHANG
INTRODUCTION 91
SULFUR-CONTAINING HETEROCYCLES 91
BENZ0[7]THI0PHER1ES 92
BENZOTHIAZOLES 95
SULTONES 98
SULTAMS 100
PHOSPHORUS-CONTAINING H
ETEROY 102
P-C HETEROCYCLES (DIBENZOPHOSPHOLE OXIDES) 102
0
-YY
=
0 HETEROCYCLES
106
YY-YY HETEROCYCLES 107
SILICON-CONTAINING HETEROCYCLES 108
BENZOSILOLES 108
OXASILINE AND AZASILINE 110
4.5 SUMMARY AND CONCLUSIONS 112
REFERENCES 113
5 RH-CATALYZED SYNTHESIS OF NITROGEN-CONTAINING
HETEROCYDES 117
KRISHNAMOORTHYMUROLIRAJAN ANDCHIEN-HONG CHENG
5.1 INTRODUCTION 117
5.2 SYNTHESIS OF FIVE-MEMBERED NITROGEN HETEROCYCLES 118
5.2.1 SYNTHESIS OF INDOLES 118
5.2.2 SYNTHESIS OF ISOINDOLINES 122
5.2.3 SYNTHESIS OF UNPROTECTED INDOLES 123
5.2.4 SYNTHESIS OF INDOLINES 124
5.2.5 SYNTHESIS OF INDAZOLES 124
5.2.6 SYNTHESIS OF ISOXAZOLES 125
5.2.7 SYNTHESIS OF PYRROLES 126
5.2.8 SYNTHESIS OF ISOINDOLINYYL
YYONES
128
5.2.9 SYNTHESIS OF 3-HYDR0XYIS0IND01IN-L0YYNES 129
5.2.10 SYNTHESIS OF 3YY(IMIN0)IS0IND01IN0NES 129 .
5.2.11 SYNTHESIS OF DIHYDROCARBAZOLES 131
5.2.12 SYNTHESIS OF SULTAMS 131
5.2.13 SYNTHESIS OF PHTHALIMIDES 132
5.3 SYNTHESIS OF SIX-MEMBERED NITROGEN HETEROCYCLES 133
5.3.1 SYNTHESIS OF ISOQUINOLINES BY RH(I) CATALYSIS 133
5.3.2 SYNTHESIS OF ISOQUINOLINES BY RH(III) CATALYSIS 134
5.33 SYNTHESIS OF L
YYAMINOISOQUINOLINES
136
5.3.4 SYNTHESIS OF ISOQUINOLONES AND RELATED DERIVATIVES 137
5.3.5 SYNTHESIS OF PHENANTHRIDINONES 142
5.3.6 SYNTHESIS OF QUINOLINES 143
5.3.7 SYNTHESIS OF NAPHTHYRIDINES 144
5.3.8 SYNTHESIS OF PHTHALAZINES 145
5.3.9 SYNTHESIS OF ACRIDINES AND PHENAZINES 145
5.3.10 SYNTHESIS OFCINNOLINES 146
5.3.11 SYNTHESIS OF ISOQUINOLINONES AND CINNOLINONES 147
5.3.12 SYNTHESIS OF DIHYDROPYRIDINES 147
5.3.13 SYNTHESIS OF PYRIDINES 148
5.3.14 SYNTHESIS OF PYRIDONES ISO
5.3.15 SYNTHESIS OF PYRIMIDINONES 150
5.4 SYNTHESIS OF QUATERNARY AMMONIUM SALTS 151
5.4.1 SYNTHESIS OF ISOQUINOLINIUM SALTS 151
5.4.2 SYNTHESIS OF QUINOLIZINIUM AND PYRIDINIUM SALTS 153
5.4.3 SYNTHESIS OFCINNOLINIUM SALTS 153
5.4.4 SYNTHESIS OF ISOQUINLINE AT-OXIDES AND PYRIDINE ^O
XIDES
154
5.5 SYNTHESIS OF SEVEN.MEMBERED NITROGEN HETEROCYCLES 155
5.5.1 SYNTHESIS OF AZEPINONES 155
5.5.2 SYNTHESIS OF L,2YYOXAZEPINES 155
7.3
7.4
7
-
4-1
749
7.4.3
74.4
7.5
7.5.1
XII I CONTENTS
5.6
YY
6.1
6.2
6
.
2.1
6
.
2
.
1.1
6
.
2
.
1.2
6.2.1.3
6
.
2.2
6
.
2
.
2.1
6
.
2
.
2.2
6.3
6.3.1
6.3.1.1
6.3.1.2
6.3.1.3
6.3.1.4
6.3.2
6.4
SUMMARY AND CONCLUSIONS 156
REFERENCES 156
RHYYCATALYZED SYNTHESIS OF OXYGEN-CONTAINING HETEROCYCLES 161
BIN LIU, FANG HU, ANDBING-FERIG SHI
INTRODUCTION 161
SYNTHESIS OF FIVE-MEMBERED OXYGEN-CONTAINING HETEROCYCLES 161
INTERMOLECULAR ANNULATION 161
PHTHALIDES 161
FURANS 103
OTHER FIVE-MEMBERED OXYGEN-CONTAINING HETEROCYCLES 165
INTRAMOLECULAR CYCLIZATION 167
DIHYDROBENZOFURANS 16/
DIBENZOFURAN 168
SYNTHESIS OF SIX.MEMBERED OXYGEN-CONTAINING HETEROCYCLES 168
INTERMOLECULAR ANNULATION 168
CHROMENES 168
CHROMONES 174
COUMARIN 175
OTHER SIX-MEMBERED OXYGEN-CONTAINING HETEROCYCLES 178
INTRAMOLECULAR CYCLIZATION 178
SYNTHESIS OF SEVEN-, EIGHTYY, AND NINE-MEMBERED OXYGEN-CONTAINING
HETEROCYCLES 179
INTERMOLECULAR ANNULATION 179
INTRAMOLECULAR CYCLIZATION 180
SUMMARY AND CONCLUSIONS 181
REFERENCES 182
RUTHENIUM-CATALYZED SYNTHESIS OF HETEROCYCLES VIA CYY
H BOND
ACTIVATION 187
BINLIANDBAIQUON WANG
INTRODUCTION 187
RUTHENIUM-CATALYZED HETEROCYCLE SYNTHESIS VIA INTRAMOLECULAR C-C
BOND FORMATION BASED ON C-H BOND ACTIVATION 188
RUTHENIUM-CATALYZED HETEROCYCLE SYNTHESIS VIA INTRAMOLECULAR C-N
BOND FORMATION BASED ON C_H BOND ACTIVATION 192
RUTHENIUM-CATALYZED HETEROCYCLE SYNTHESIS VIA INTERMOLECULAR
C-C/C-O BOND FORMATION BASED ON C-H BOND ACTIVATION 194
CYCLIZATION WITH ALKYNES 194
CYCLIZATION WITH ALKENES 198
CYCLIZATION WITH CARBON MONOXIDE 201
CYCLIZATIONWITHL,2-DIOL 202
RUTHENIUM-CATALYZED HETEROCYCLE SYNTHESIS VIA INTERMOLECULAR
C-C/C-N BOND FORMATION BASED ON C-H BOND ACTIVATION 203
CYCLIZATION WITH ALKYNES 203
4
.
4
YY
6
6
6
7
.
1
7.2
7.5.2 CYCLIZATION WITH ALKENES 220
7.5.3 CYCLIZATION WITH CARBON MONOXIDE 225
7.5.4 CYCLIZATION WITH ISOCYANATE 228
7.6 SUMMARY AND CONCLUSIONS YY
REFERENCES 229
YY
CU-CATALYZED HETEROCYCLE SYNTHESIS 233
FENG CHEN AND HING JIAO
8.1 INTRODUCTION 233
8.2 FOUR
YYYY
MEMBEREDYYRING FORMATION 233
8.3 FIVE-MEMBERED-RING FORMATION 234
8.3.1 COPPER-CATALYZED SYNTHESIS OF PYRROLES 234
8.3.2 COPPER-CATALYZED SYNTHESIS OF PYRROLIDINES 237
8.3.3 COPPER-CATALYZED SYNTHESIS OF INDOLES 240
8.3.4 COPPER-CATALYZED SYNTHESIS OF INDOLINES 242
8.3.5 COPPER-CATALYZED SYNTHESIS OFOXINDOLES 245
8.3.6 COPPER-CATALYZED SYNTHESIS OFINDOLE
YYYY
2,3
YY
(LIONE (ISATINS)
248
8.3.7 COPPER-CATALYZED SYNTHESIS OF INDOLIZINES 250
8.3.8 COPPER-CATALYZED SYNTHESIS OF CARBAZOLES 250
8.3.9 COPPER-CATALYZED SYNTHESIS OF IMIDAZOLES 251
8.3.10 COPPER-CATALYZED SYNTHESIS OF BENZIMIDAZOLES 254
8.3.11 COPPER-CATALYZED SYNTHESIS OF IMIDAZOPYRIDINES 256
8.3.12 COPPER-CATALYZED SYNTHESIS OFPYRAZOLES AND INDAZOLES 260
8.3.13 COPPER-CATALYZED SYNTHESIS OFOXAZOLES 261
8.3.14 COPPER-CATALYZED SYNTHESIS OF B
EN
ZOX
262
8.3.15 COPPER-CATALYZED SYNTHESIS OF L,2,3YYTRIAZOLES 263
8.3.16 COPPER-CATALYZED SYNTHESIS OFL,2,3-TETRAZ01ES 264
8.3.17 COPPER-CATALYZED SYNTHESIS OFFURANS 264
8.4 SIXYYMEMBEREDYYRING FORMATION 266
8.4.1 COPPER-CATALYZED SYNTHESIS OF PYRIDINES 266
8.4.2 COPPER-CATALYZED SYNTHESIS OF QUINOLINES 267
8.4.3 . COPPER-CATALYZED SYNTHESIS OF ISOQ^^ 271
8.4.4 COPPER-CATALYZED SYNTHESIS OFQUINOLINONES 272
8.4.5 COPPER-CATALYZED SYNTHESIS OFACRIDONES 273
8.4.6 COPPER-CATALYZED SYNTHESIS OFPHENANTHRIDINE 275
8.4.7 COPPER-CATALYZED SYNTHESIS OF QUINAZOLINE AND
QUINAZOLINONES 276
8.4.8 COPPER-CATALYZED SYNTHESIS OFCINNOLINES 277
8.4.9 COPPER-CATALYZED SYNTHESIS OF PYRIMIDINONE 278
8.4.10 COPPER.CATALYZED SYNTHESIS OF L,4YYDIHYDROPYRAZINE
DERIVATIVES 278
8.4.11 COPPER-CATALYZED SYNTHESIS 0
F
L,3
0
YYXAZINES
279
8.4.12 COPPER-CATALYZED SYNTHESIS OF OXAZN^^ 280
8.4.13 COPPER-CATALYZED SYNTHESIS OFCHROMAN DERIVATIVES 280
8.4.14 COPPER-CATALYZED SYNTHESIS OFBENZOLACTONE DERIVATIVES 281
8.4.15
8.4.16
8.4.17
8.5
Q
9.1
9.2
YY
91
9.2.2
9.3
9.3.1
9.3.2
9.4
10
10.1
10.2
10.3
10.4
10.5
11
11.1
11.2
11
.
2.1
11
.
2.2
11.2.3
11.3
11.3.1
COPPER-CATALYZED SYNTHESIS OF COUMARIN DERIVATIVES 282
COPPER-CATALYZED SYNTHESIS OF XANTHONE DERIVATIVES 283
COPPER-CATALYZED SYNTHESIS OF N,SYYHETEROCYCLES 284
SUMMARY 285
REFERENCES 285
FE- AND YYYY-CATALYZED SYNTHESIS OF HETEROCYCLES 291
JIN-HENG YYYY
YY AND REN-JIE SONG
INTRODUCTION 291
IRON-CATALYZED SYNTHESIS OF HETEROCYCLES 291
IRON-CATALYZED SYNTHESIS OF NITROGEN-CONTAINING HETEROCYCLES 292
IRON-CATALYZED SYNTHESIS OF OXYGEN-CONTAINING HETEROCYCLES 304
SILVER-CATALYZED SYNTHESIS OF HETEROCYCLES 307
SILVER-CATALYZED SYNTHESIS OFNITROGEN-CONTAINING
HETEROCYCLES 308
SILVER CATALYZED SYNTHESIS OF OXYGENYY OR PHOSPHORUS-CONTAINING
HETEROCYCLES 311
CONCLUSION AND OUTLOOK 312
REFERENCES 314
HETEROCYCLES SYNTHESIS VIA CO-CATALYZED C-H BOND
FUNCTIONALIZATION 317
NAOHIKOYOSHIKAI
INTRODUCTION 317
HETEROCYCLE SYNTHESIS VIA LOW-VALENT COBALT-CATALYZED C-H
ACTIVATION 319
HETEROCYCLE SYNTHESIS VIA HIGH-VALENT COBALT-CATALYZED C-H
ACTIVATION 325
HETEROCYCLE SYNTHESIS VIA C-H FUNCTIONALIZATION UNDER C
0
(II)-BASED
METALLORADICAL CATALYSIS 331
SUMMARY AND CONCLUSIONS 335
REFERENCES 335
IR.CATALYZED HETEROCYCLES SYNTHESIS 339
YASUSHI OBORA
INTRODUCTION 339
IRYYCATALYZED HETEROCYCLIZATION BY ORTHO-KXYL C-H ACTIVATION 340
IRYYCATALYZED [3+2] CYCLIZATION OFKETIMINES WITH
L,3YYDIENES/ALKYNES 340
IRYYCATALYZED CYCLIZATION OF BENZOIC ACID TO GIVE
2YYHYDR0XY6YYHYYBENZ0[C]CHR0M
EN0
YY6YY
NES
342
IR-CATALYZED CYCLIZATION OFAS-ARYLCARBAMOYL CHLORIDES WITH
ALKYNES 342
IR-CATALYZED HETEROCYCLIZATION BY BENZYLIC C-H ACTIVATION 343
IRYYCATALYZED ASYYCYCLIZATION OF ARYL AZIDES 343
11.3.2
IR-CATALYZED SILYLATION OFBENZYLIC AMINES AND 2,ASYYDIALKYLANILINES
VIA ARYL C-H BOND ACTIVATION 343
11.4 IR-CATALYZED HETEROCYCLIZATION BY SP3 C-H ACTIVATION 344
11.4.1 IRYYCATALYZED N-CYCLIZATION OF ARYL AZIDES 344
11.5 HETEROCYCLIZATION BY IR CATALYST AS LEWIS ACID 345
11.6 IR-CATALYZED HETEROCYCLIZATION BY C-H BOND ACTIVATION THROUGH
TRANSFER HYDROGENATION 345
11.6.1 IRYYCATALYZED "-HETEROCYCLIZATION OF NAPHTHYLAMINES WITH
DIOLS 345
11.6.2 IRYYCATALYZED REACTION OF ANILINES WITH DIOLS TO GIVE
2,3-DISUBSTITUTED INDOLES 346
11.6.3 IR-CATALYZED SYNTHESIS OF INDOLE FROM 2YYAMINOARYL ETHYL
ALCOHOL 347
11.6.4 IR CATALYSTS WITH PYRAZOYL AND PYRAZOYLYYL,2,3YYBIDENTATE (YY-YY)
LIGANDS FOR THE SYNTHESIS OF TRICYCLIC INDOLES 347
11.7 MISCELLANEOUS REACTIONS 349
11.7.1 IRYYCATALYZED ARYLATIVE CYCLIZATION OFALKYNONES WITH ARYLBORONIC
ACID 349
11.7.2 AA-HETEROCYCLIZATION OF AMINOALCOHOL BY IR CATALYST WITH A
TRIAZOLYL-DIYLIDENE LIGAND 349
11.7.3 SYNTHESIS OF INDOLES FROM AMINOALCOHOL AND ALKYNYL ALCOHOLS BY
IR-PT CATALYST 350
11.7.4 SYNTHESIS OF PYRR010[L,2YYCT]QUIN0XALINES BY IRIDIUM
COMPLEX-CATALYZED ANNULATION OF 2YYALKYLQUINOXALKINES 351
11.7.5 IRYYMOFYYCATALYZED HYDROSILYLATION/ORI/ZYYYYSILYLATION TO
BENZOXASILOLES 352
11.7.6 SYNTHESIS OF FURANES AND PYRROLES INVOLVING ALKYLATION OF
L,3YYDICARBONYL COMPOUNDS BY IRIDIUM-TIN BIMETALLIC
CATALYST 353
11.8 SUMMARY AND CONCLUSIONS 353
REFERENCES 354
12 AU- AND PT-CATALYZED C-H ACTIVATION/FUNCTIONALIZATIONS FOR THE
SYNTHESIS OF HETEROCYCLES 359
YUANJINGXIAO ANDJUNLIANG ZHANG
12.1 INTRODUCTION 359
12.2 SYNTHESIS OF O-HETEROCYCLES 360
12.2.1 SYNTHESIS OF FIVE-MEMBERED O-HETEROCYCLES 360
12.2.1.1 VIA YYYY-CATALYZED C(SP)-H FUNCTIONALIZATION 360
12.2.1.2 VIA AUYYCATALYZED ARYL C(SP2)-H FUNCTIONALIZATION 360
12.2.1.3 VIA YYYY-CATALYZED C(SP3)-H FUNCTIONALIZATION
362
12.2.1.4 VIA PT.CATALYZED C(SP3)-H FUNCTIONALIZATION 362
12.2.1.5 VIA YYYY-CATALYZED C(SP)-H AND C(SP3)YYH FUNCTIONALIZATION 362
12.2.2 SYNTHESIS OFSIX.MEMBERED O.HETEROCYCLES 363
12.2.2.1 VIA AUYYCATALYZED C(SP)-H FUNCTIONALIZATION 363
12.2.2.2 VIA AUYYCATALYZED FORMYL C(SP2)-H FUNCTIONALIZATION 364
12.2.2.3 VIA AUYYCATALYZED ARYL C(SP2)-H FUNCTIONALIZATION 365
12.2.2.4 VIA AUYYCATALYZED C(SP3)-H FUNCTIONALIZATION
367
12.3 SYNTHESIS OFN-HETEROCYCLES 369
12.3.1 SYNTHESIS OF FIVE.MEMBERED ASYYHETEROCYCLES 369
12.3.1.1 VIA AUYYCATALYZED C(SP)-H FUNCTIONALIZATION 369
12.3.1.2 VIA AU.CATALYZED C(SP)-H AND ALKENYL C(SP2)-YYH
FUNCTIONALIZATION YY
12.3.1.3 VIA AUYYCATALYZED C(SP)-H
YY
C(SP3)-H
YY
OR ARYL C(SP2)-H
FUNCTIONALIZATION 369
12.3.1.4 VIA AUYYCATALYZED ARYL C(SP2)-H FUNCTIONALIZATION 370
12.3.1.5 VIA AUYYCATALYZEDC(SP3)-H FUNCTIONALIZATION 374
12.3.1.6 VIA YYYY-CATALYZED MISCELLANEOUS REACTIONS 374
12.3.2 SYNTHESIS OF SIXYYMEMBERED AS-HETEROCYCLES 376
12321 VIA AUYYCATALYZED C(SP)-H AND ARYL C(SP2)-H
FUNCTIONALIZATION 376
12.3.2.2 VIA AU.CATALYZED FORMYL C(SP2)-H FUNCTIONALIZATION 376
12.3.2.3 VIA AUYYCATAIYZED C(SP)-H AND C(SP3)_H FUNCTIONALIZATION 377
12.3.2.4 VIA AU.CATALYZED ARYL C(SP2)-H FUNCTIONALIZATION 377
12.3.2.5 VIA PTYYCATALYZED ARYL C(SP2)-H FUNCTIONALIZATION 379
12.3.2.6 VIA YYYY-CATALYZED C(SP3)-H FUNCTIONALIZATION 380
12.3.3 SYNTHESIS OF SEVEN.MEMBERED N
YYHETEROCYCLES
382
12.3.3.1 VIA YYYY-CATALYZED C(SP2)-H FUNCTIONALIZATION 382
12.3.3.2 VIA YYYY-CATALYZED C(SP3)-H FUNCTIONALIZATION 382
12.4 SYNTHESIS OF .YY.HETEROCYCLES 383 -
12.4.1 SYNTHESIS OF SEVEN-MEMBERED .S-HETEROCYCLES VIA AU-CATALYZED
ARYL C(SP2)-H FUNCTIONALIZATION 383
12.5 SYNTHESIS OFO-HETEROCYCLES AND N-HETEROCYCLES 383
12.5.1 SYNTHESIS OF FIVE-MEMBERED O-HETEROCYCLES AND
^-HETEROCYCLES 383
12.5.1.1 VIA AU-CATALYZED C(SP)-H FUNCTIONALIZATION 383
12.5.1.2 VIA AU.CATALYZED ARYL C(SP2)-H FUNCTIONALIZATION 385
12.5.2 SYNTHESIS OT B
1
XYYMEMBERED O-HETEROCYCLES AND
AA-HETEROCYCLES 386
12.5.2.1 VIA PT OR AU.CATALYZED ARYL C(SP2)-H FUNCTIONALIZATION 386
12.6 SYNTHESIS OF FUSED POLYCYCLIC POLYHETEROCYCLES 389
12.6.1 VIA AU-CATALYZED ARYL C(SP2)-H FUNCTIONALIZATION 389
12.6.2 VIA AU- OR PT-CATALYZED ARYL C(SP2)-H FUNCTIONALIZATION 393
32.6
YY
VIA PTYYCATALYZED ARYL C(SP2)-H FUNCTIONALIZATION 394
12.6.4 VIA AU.CATALYZED C(SP3)_H FUNCTIONALIZATION 395
12.6.5 VIA PTYYCATALYZED C(SP3)-H FUNCTIONALIZATION 396
12.7 CONCLUSIONS 397
REFERENCES 398
13
13.1
13.2
13.2.1
13.2.2
13.3
13.3.1
13.3.2
13.3.3
13.4
14
14.1
149
14.3
144
15
15.1
15.2
15.2.1
15.3
15.3.1
15.4
15.4.1
15.4.2
15.5
15.5.1
15.5.2
15.5.3
HETEROCYCLE SYNTHESIS BASED ON VISIBLE-LIGHMNDUCED PHOTOCATALYTIC
C.H FUNCTIONALIZATION 403
WEI DING, WEI GUO, TING-TING ZENG, LIANG-QIU LU AND WEN-JING XIAO
INTRODUCTION 403
DE NOVO SYNTHESIS OF HETEROCYCLES 404
PHOTOCATALYTIC SP3 C-H FUNCTIONALIZATION FOR HETEROCYCLE
SYNTHESIS 404
PHOTOCATALYTIC SP2 C-H FUNCTIONALIZATION FOR HETEROCYCLE
SYNTHESIS 415
DIRECT C-H FUNCTIONALIZATION OF HETEROARENES 427
THE PHOTOCATALYTIC ALKYLATION OF HETEROARENES 427
THE PHOTOCATALYTIC ARYLATION OF HETEROARENES 437
THE PHOTOCATALYTIC AMINATION AND SULFURATION OF HETEROARENES 439
SUMMARY AND OUTLOOK 443
REFERENCES 444
HETEROGENEOUS C-H ACTIVATION FOR THE HETEROCYCLE SYNTHESIS 449
LIN HE AND MATTHIAS BEUER
INTRODUCTION 449
HETEROGENEOUS PDYYCATALYZED HETEROCYCLE SYNTHESIS VIA
C_H ACTIVATION 450
HETEROGENEOUS PHOTOCATALYSIS FOR THE HETEROCYCLE SYNTHESIS VIA
C-H ACTIVATION 460
SUMMARY 464
REFERENCES 464
TRANSITION METAL-CATALYZED CARBONYLATIVE SYNTHESIS OF HETEROCYCLES
VIA C-H ACTIVATION 467
JIANBIN CHEN ONDXIOO-FENG WU
INTRODUCTION 467
COBALT-CATALYZED HETEROCYCLIC SYNTHESIS VIA CARBONYLATIVE
C-H ACTIVATION 468
FIVE-MEMBERED RING SYNTHESIS 468
RHODIUM-CATALYZED HETEROCYCLIC SYNTHESIS VIA CARBONYLATIVE
C-H ACTIVATION 471
FIVE-MEMBERED RING SYNTHESIS 471
RUTHENIUM-CATALYZED HETEROCYCLIC SYNTHESIS VIA CARBONYLATIVE
C-H ACTIVATION 472
FIVEYYMEMBERED RING SYNTHESIS 472
SIX-MEMBERED RING SYNTHESIS 476
PALLADIUM-CATALYZED HETEROCYCLIC SYNTHESIS VIA CARBONYLATIVE
C-H ACTIVATION 477
FOUR-MEMBERED RING SYNTHESIS 477
FIVE.MEMBERED RING SYNTHESIS 479
SIXYYMEMBERED RING SYNTHESIS 485
15.6
16
16.1
16.2
16.2.1
16.2.1.1
16.2.1.2
16.2.1.3
1
^
9
1
4
YY
.
16.2.1
16.2.1.6
16.2.1.7
16.2.1.8
16.2.1.9
16.2.1.10
16.2.2
16.2.2.1
16.2.2.2
16.2.2.3
16.2.2.4
16.2.3
16.2.3.1
16.23.2
16.2.3.3
16.2.4
16.2.4.1
16.2.4.2
SUMMARY AND OUTLOOK
SOO
REFERENCES 501
SYNTHESIS OF NATURAL PRODUCTS AND PHARMACEUTICALS VIA CATALYTIC C-H
FUNCTIONALIZATION 505
JUNICHIRO YOMOGUCHI, KOZUMAAMAIKE, ANDKENICHIRO ITAMI
INTRODUCTION SOS
NATURAL PRODUCTS CONTAINING HETEROAROMATICS 505
INDOLES AND RELATED COMPOUNDS SOS
DRAGMACIDIN D (C-H ARYLATION OF INDOLES AT THE YYYY POSITION) 507
CLAVICIPITIC ACID (C-H ALKENYLATION OF INDOLES AT THE YYYY
POSITION) 507
PARAHERQUAMIDE B (INTRAMOLECULAR C-H ALKYLATION OF INDOLES AT THE
C2 POSITION) 507
PKC INHIBITOR (INTRAMOLECULAR C-H ALKYLATION OF INDOLES AT THE C2
POSITION) 509
CLAVICIPITIC ACID (C-H ALKENYLATION OF INDOLES AT THE C4
POSITION) SII
HIPPADINE (C-H BORYLATION OF INDOLES AT THE C7 POSITION) 511
DICTYODENDRIN B (C-H ARYLATION OF PYRROLES AT THE YYYY POSITION, C-H
BORYLATION OF INDOLES AT THE C7 POSITION, AND NITRENE C-H INSERTION
OF INDOLES AT THE C4 POSITION) 512
PAULLONE (OXIDATIVE LAROCK INDOLE SYNTHESIS) 514
HORSFILINE (INDOLE SYNTHESIS BY INTERMOLECULAR C-H COUPLING) YY
14
DIMEBOLIN (INDOLE SYNTHESIS BY NITRENOID C-H INSERTION
REACTION) 515
PYRROLES AND RELATED COMPOUNDS 516
RHAZINILAM (INTRAMOLECULAR AND INTERMOLECULAR C-H ARYLATION OF
PYRIOLES AT THE C4 POSITION) 516
RHAZINILAM AND ASPIDOSPERMIDINE (C-H BORYLATION AND C-H
ALKYLATION OF PYRROLES AT THE C4 AND C5 POSITIONS) 518
LAMELLARINS
C
AND I (INTER- AND INTRAMOLECULAR C-H ARYLATION OF
PYRROLES AT THE C2, YYYY, AND C4 POSITIONS) 518
DICTYODENDRINS A AND F (C-H ARYLATION AND C-H INSERTION OF
PYRROLES ON C2, YYYY, AND C5 POSITION) 521
CARBAZOLES AND RELATED COMPOUNDS 522
CLAUSINE P AND GLYCOZOLIDINE (SYNTHESIS OF CARBAZOLES BY
INTRAMOLECULAR AR-H/AR-X ARYLATION) 522
CLAUSENINE (SYNTHESIS OF CARBAZOLES BY INTRAMOLECULAR C-H/C-H
ARYLATION) 523
CLAUSINE C AND GLYCOZOLINE (SYNTHESIS OF CARBAZOLES BY
INTRAMOLECULAR C-H AMINATION) 524
BENZOFURAN AND RELATED COMPOUNDS 524
FRONDOSIN B (C-H ALKENYLATION OF BENZOFURAN) 524
DIPTOINDONESIN G (C-H ARYLATION OF BENZOFURAN) 525
16.2.4.3 LITHOSPERMIC ACID (FORMATION OF DIHYDROBENZOFURAN USING
C-HALKYLATION) 526
16.2.4.4 LITHOSPERMIC ACID (FORMATION OF DIHYDROBENZOFURAN USING
C-H INSERTION AND C-H ALKENYLATION AT THE C4 POSITION OF
DIHYDROBENZOFURAN) 526
16.2.4.5 MORPHINE (INTRAMOLECULAR C-HINERTION TO
DIHYDROBENZOFURAN) 527
16.2.5 IMIDAZOLES OXAZOLES, YYAZOLES, AND RELATED LOMPOUNDS 528
16.2.5.1 JNK3 INHIBITORS (C-H ALKYLATION OF IMIDAZOLES) 528
16.2.5.2 TYROSINE KINASE INHIBITOR (C-H ARYLATION OF IMIDAZOLES) 529
16.2.5.3 TEXALINE, FEBUXOSTAT, AND MUSCORIDE A (C-H ARYLATION OF
OXAZOLES
OR YYAZOLES) 531
16.2.5.4 ANNULOLINE AND SIPHONAZOLE B (C-H ALKENYLATION OF OXAZOLES AT
THE
C2 POSITION) 534
16.2.6 QUINAZOLINES AND RELATED COMPOUNDS 535
16.2.6.1 LUOTONIN B (INTRAMOLECULAR C-H ARYLATION OF QUINAZOLINE) 535
16.2.6.2 VASICOLINE (C-H ALKYLATION OF QUINAZOLINE) 535
16.2.7 QUINOLINES, ISOQUINOLINES, PHENANTHRIDINES, AND RELATED
COMPOUNDS 536
16.2.7.1 NORCHELERYTHRINE (INTRAMOLECULAR C-H ARYLATION) 536
16.2.7.2 NITIDINE AND NK 109 (CATELLANI-TYPE C-H
ARYLATIONW.ARYLATION) 536
16.2.7.3 LYYB4 ANTAGONIST AND MCH-1R RECEPTOR MODULATOR
(SP3 C-H ARYLATION/INTRAMOLECULAR C-H AMINATION) 537
16.2.7.4 TIPIFARNIB (C-H ALKENYLATION AND CYCLIZATION) 537
16.2.7.5 OXYCHELERYTHRINE (C-H ALKENYLATION AND ANNULATION) 538
16.2.8 PYRIDINES AND RELATED COMPOUNDS 539
16.2.8.1 SODIUM CHANNEL INHIBITOR AND ANTIMALARIAL AGENT (C-H ARYLATION
OF PYRIDINES AT THE C2 POSITION) 539
16.2.8.2 COMPLANADINE A AND YY (C-H BORYLATION OF PYRIDINE AT YYYY
POSITION
OR C-H ARYLATION OF PYRIDINES AT C2 POSITION) 539
16.2.8.3 ANABASHINE (C-H ARYLATION OFLMINOPYRIDIUM YLIDES) 540
16.2.8.4 PRECLAMOL (C-H ARYLATION OF PYRIDINE AT THE YYYY POSITION) 542
16.2.9 OTHER HETEROCYCLES 542
16.2.9.1 CELECOXIB (C-H ARYLATION OF PYRAZOLES) 542
16.2.9.2 GABA 2/3 AGONIST (C-H ARYLATION OF IMIDAZOPYRIMIDINES) 543
16.2.9.3 NIGELLIDINE HYDROBROMIDE, YD-3, AND Y
C
L (C-H ARYLATION OF
INDAZOLES) 543
16.2.9.4 PSEUDOHELIOTRIDANE (FORMATION OF PYRROLIDINES USING SP3 C-H
INSERTION) 544
16.2.9.5 AERUGINOSIN (SP3 C-H ALKENYLATION AND ARYLATION) 545
16.3 SUMMARY 546
REFERENCES 547
\
YY
VDEX SSI |
| any_adam_object | 1 |
| author2 | Wu, Xiao-Feng 1985- |
| author2_role | edt |
| author2_variant | x f w xfw |
| author_GND | (DE-588)1019231688 |
| author_facet | Wu, Xiao-Feng 1985- |
| building | Verbundindex |
| bvnumber | BV043526539 |
| classification_rvk | VK 5560 VK 7200 |
| ctrlnum | (OCoLC)915163482 (DE-599)DNB1074254694 |
| dewey-full | 540 |
| dewey-hundreds | 500 - Natural sciences and mathematics |
| dewey-ones | 540 - Chemistry and allied sciences |
| dewey-raw | 540 |
| dewey-search | 540 |
| dewey-sort | 3540 |
| dewey-tens | 540 - Chemistry and allied sciences |
| discipline | Chemie / Pharmazie |
| format | Book |
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| genre | (DE-588)4143413-4 Aufsatzsammlung gnd-content |
| genre_facet | Aufsatzsammlung |
| id | DE-604.BV043526539 |
| illustrated | Illustrated |
| indexdate | 2025-03-10T15:04:35Z |
| institution | BVB |
| isbn | 9783527338887 9783527691920 |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-028942332 |
| oclc_num | 915163482 |
| open_access_boolean | |
| owner | DE-11 DE-703 DE-19 DE-BY-UBM |
| owner_facet | DE-11 DE-703 DE-19 DE-BY-UBM |
| physical | XXXI, 562 Seiten Illustrationen (teilweise farbig) |
| publishDate | 2016 |
| publishDateSearch | 2016 |
| publishDateSort | 2016 |
| publisher | Wiley-VCH Verlag GmbH & Co. KGaA |
| record_format | marc |
| spelling | Transition metal-catalyzed heterocycle synthesis via C-H activation edited by Xiao-Feng Wu Weinheim Wiley-VCH Verlag GmbH & Co. KGaA [2016] © 2016 XXXI, 562 Seiten Illustrationen (teilweise farbig) txt rdacontent n rdamedia nc rdacarrier Katalyse (DE-588)4029921-1 gnd rswk-swf Heterocyclische Verbindungen (DE-588)4159726-6 gnd rswk-swf Chemische Synthese (DE-588)4133806-6 gnd rswk-swf Übergangsmetallverbindungen (DE-588)4061385-9 gnd rswk-swf Catalysis Chemie Chemistry Katalyse Metallorganische Verbindungen Nachhaltige u. Grüne Chemie Nachhaltigkeit Organometallchemie Organometallic Chemistry Pharmaceutical & Medicinal Chemistry Pharmazeutische u. Medizinische Chemie Sustainable Chemistry & Green Chemistry (DE-588)4143413-4 Aufsatzsammlung gnd-content Heterocyclische Verbindungen (DE-588)4159726-6 s Chemische Synthese (DE-588)4133806-6 s Katalyse (DE-588)4029921-1 s Übergangsmetallverbindungen (DE-588)4061385-9 s DE-604 Wu, Xiao-Feng 1985- (DE-588)1019231688 edt Erscheint auch als Online-Ausgabe, EPUB 978-3-527-69193-7 Erscheint auch als Online-Ausgabe, MOBI 978-3-527-69194-4 Erscheint auch als Online-Ausgabe, PDF 978-3-527-69191-3 X:MVB text/html http://deposit.dnb.de/cgi-bin/dokserv?id=5327578&prov=M&dok_var=1&dok_ext=htm Inhaltstext DNB Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=028942332&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Transition metal-catalyzed heterocycle synthesis via C-H activation Katalyse (DE-588)4029921-1 gnd Heterocyclische Verbindungen (DE-588)4159726-6 gnd Chemische Synthese (DE-588)4133806-6 gnd Übergangsmetallverbindungen (DE-588)4061385-9 gnd |
| subject_GND | (DE-588)4029921-1 (DE-588)4159726-6 (DE-588)4133806-6 (DE-588)4061385-9 (DE-588)4143413-4 |
| title | Transition metal-catalyzed heterocycle synthesis via C-H activation |
| title_auth | Transition metal-catalyzed heterocycle synthesis via C-H activation |
| title_exact_search | Transition metal-catalyzed heterocycle synthesis via C-H activation |
| title_full | Transition metal-catalyzed heterocycle synthesis via C-H activation edited by Xiao-Feng Wu |
| title_fullStr | Transition metal-catalyzed heterocycle synthesis via C-H activation edited by Xiao-Feng Wu |
| title_full_unstemmed | Transition metal-catalyzed heterocycle synthesis via C-H activation edited by Xiao-Feng Wu |
| title_short | Transition metal-catalyzed heterocycle synthesis via C-H activation |
| title_sort | transition metal catalyzed heterocycle synthesis via c h activation |
| topic | Katalyse (DE-588)4029921-1 gnd Heterocyclische Verbindungen (DE-588)4159726-6 gnd Chemische Synthese (DE-588)4133806-6 gnd Übergangsmetallverbindungen (DE-588)4061385-9 gnd |
| topic_facet | Katalyse Heterocyclische Verbindungen Chemische Synthese Übergangsmetallverbindungen Aufsatzsammlung |
| url | http://deposit.dnb.de/cgi-bin/dokserv?id=5327578&prov=M&dok_var=1&dok_ext=htm http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=028942332&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT wuxiaofeng transitionmetalcatalyzedheterocyclesynthesisviachactivation |