Catalyzed carbon-heteroatom bond formation:
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2011
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| Beschreibung: | XVIII, 505 S. graph. Darst. |
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IMAGE 1
CONTENTS
PREFACE XIII LIST OF CONTRIBUTORS XV
1 SYNTHESIS OF SATURATED FIVE-MEMBERED NITROGEN HETEROCYCLES VIA
PD-CATALYZED C-N BOND-FORMING REACTIONS 1 JOHN P. WOLFE, JOSHUA D.
NEUKOM, AND DUY H. MAI 1.1 INTRODUCTION 2
1.2 PD-CATALYZED AMINATION OF ARYL HALIDES 1 1.3 SYNTHESIS OF SATURATED
NITROGEN HETEROCYCLES VIA ALKENE, ALKYNE, OR ALLENE AMINOPALLADATION
REACTIONS 3
1.3.1 PD"-CATALYZED OXIDATIVE AMINATION OF ALKENES 4 1.3.2 PD-CATALYZED
HYDROAMINATION REACTIONS OF ALKENES AND ALKYNES 6 1.3.3 PD-CATALYZED
CARBOAMINATION REACTIONS OF ALKENES 8 1.3.4 PD"-CATALYZED CARBOAMINATION
REACTIONS OF ALKENES 10 1.3.5 PD-CATALYZED CARBOAMINATION REACTIONS OF
ALKYNES, ALIENES,
AND DIENES 10
1.3.6 VICINAL DIFUNCTIONALIZATION OF ALKENES AND ALIENES 13 1.4
SYNTHESIS OF NITROGEN HETEROCYCLES VIA INTERMEDIATE JR-ALLYLPALLADIUM
COMPLEXES 16
1.4.1 REACTIONS INVOLVING OXIDATIVE ADDITION OF ALLYLIC ELECTROPHILES 16
1.4.2 REACTIONS INVOLVING 7T-ALLYLPALLADIUM INTERMEDIATES GENERATED VIA
ALKENE CARBOPALLADATION 1 9 1.4.3 REACTIONS INVOLVING AMINOPALLADATION
OF 1,3-DIENES 21
1.4.4 GENERATION OF AJLYLPALLADIUM INTERMEDIATES THROUGH C-H ACTIVATION
21 1.5 SYNTHESIS OF NITROGEN HETEROCYCLES VIA PD-CATALYZED 1,3-DIPOLAR
CYCLOADDITION REACTIONS 22
1.6 SYNTHESIS OF NITROGEN HETEROCYCLES VIA CARBONYLATIVE PROCESSES 23
1.6.1 TRANSFORMATIONS INVOLVING CO INSERTION INTO ARYL OR ALKENYL
PD-CARBON BONDS 23
CATALYZED CARBON-HETEROATOM BOND FORMATION. EDITED BY ANDREI K. YUDIN
COPYRIGHT 2011 WILEY-VCH VERLAG GMBH & CO. KGAA, WEINHEIM ISBN:
978-3-527-32428-6
BIBLIOGRAFISCHE INFORMATIONEN HTTP://D-NB.INFO/100097393X
DIGITALISIERT DURCH
IMAGE 2
VI CONTENTS
1.6.2 TRANSFORMATIONS INVOLVING CO INSERTION INTO A PD-HETEROATOM
BOND 25
1.6.3 WACKER-TYPE CARBONYLATIVE PROCESSES 26 1.7 SUMMARY AND FUTURE
OUTLOOK 28 REFERENCES 28
2 TRANSITION METAL CATALYZED APPROACHES TO LACTONES INVOLVING C-O BOND
FORMATION 35
CHARLES S. YEUNG, PETER K. DOMAN, AND VY M. DONG 2.1 INTRODUCTION 35
2.2 SYNTHESIS OF LACTONES INVOLVING CO 36 2.2.1 CARBONYLATIONOF C-X
BONDS 36 2.2.2 CARBONYLATION OF C-M BONDS 39 2.2.3 HYDROCARBONYLATION OF
C=C AND C=C BONDS 40 2.2.4 CARBOCARBONYLATION OF C=C AND CSC BONDS 42
2.2.5 HETEROCARBONYLATION OF C=C AND C=C BONDS 43 2.2.6 MISCELLANEOUS
LACTONE SYNTHESES INVOLVING CO 45 2.3 SYNTHESIS OF LACTONES VIA C=C AND
CSC ADDITION 46 2.3.1 HYDROCARBOXYLATION OF C=C AND C=C BONDS 46
2.3.2 CARBO- AND OXY-CARBOXYLATION OF C=C AND C=C BONDS 50 2.4 SYNTHESIS
OF LACTONES VIA C=O HYDROACYLATION 52 2.4.1 ALDEHYDE HYDROACYLATION 52
2.4.2 KETONE HYDROACYLATION 53 2.4.3 [4 + 2] ANNULATION 55 2.5
MISCELLANEOUS SYNTHESES OF LACTONES 56 2.5.1 OXIDATIVE LACTONIZATION OF
DIOLS 56 2.5.2 REDUCTIVE CYCLIZATION OF KETOACIDS AND KETOESTERS 57
2.5.3 C-H OXYGENATION 58 2.5.4 RING CLOSURE OF BENZOIC ACIDS WITH
DIHALOALKANES 59 2.5.5 BAEYER-VILLIGER OXIDATION OF CYCLIC KETONES 60
2.5.6 RING OPENING OF CYCLOPROPANES WITH CARBOXYLIC ACIDS 60 2.5.7 RING
CLOSURE OF O-IODOBENZOATES WITH ALDEHYDES 61 2.5.8 SYNTHESIS OF LACTONES
INVOLVING CO 2 62 2.5.9 MICHAEL ADDITION OF A,SS-UNSATURATED
N-ACYLPYRROLIDINES 62 2.5.10 [2 + 2] CYCLOADDITION OF KETENES AND
ALDEHYDES 63 2.5.11 TANDEM CROSS-METATHESIS/HYDROGENATION ROUTE TO
LACTONES 63 2.5.12 MODERN CATALYTIC VARIANTS OF CLASSICAL
MACROLACTONIZATIONS 64 2.6 CONCLUSIONS AND OUTLOOK 65
REFERENCES 65
3 THE FORMATION OF CSP 2-S AND CSPZ-SE BONDS BY SUBSTITUTION AND
ADDITION REACTIONS CATALYZED BY TRANSITION METAL COMPLEXES 69 IRINA P.
BELETSKAYA AND VALENTINE P. ANANIKOV 3.1 INTRODUCTION 69
3.2 CATALYTIC CROSS-COUPLING REACTIONS 70
IMAGE 3
CONTENTS VII
3.2.1 PD-CATALYZED TRANSFORMATIONS 70
3.2.2 NI-CATALYZED TRANSFORMATIONS 77 3.2.3 CU-CATALYZED TRANSFORMATIONS
79 3.2.4 OTHER TRANSITION METALS AS CATALYSTS 88 3.3 CATALYTIC ADDITION
OF RZ-ZR DERIVATIVES TO ALKYNES (Z=S, SE) 90 3.3.1 PD AND NI-CATALYZED
FORMATION OF VINYL CHALCOGENIDES 90 3.3.2 NI-CATALYZED SYNTHESIS OF
DIENES 200 3.3.3 RH-CATALYZED REACTIONS 202 3.3.4 CATALYTIC ADDITION OF
S-X AND SE-X BONDS TO ALKYNES 202 3.3.5 CATALYTIC ADDITION TO ALIENES
103 3.4 CATALYTIC ADDITION OF RZ-H DERIVATIVES TO ALKYNES (ZSS, SE) 204
3.4.1 PD AND NI-CATALYZED ADDITION OF THIOLS AND SELENOLS 204 3.4.2 RH
AND PT-CATALYZED ADDITION OF THIOLS TO ALKYNES 209 3.4.3 CATALYTIC
ADDITION OF THIOLS AND SELENOLS TO ALIENES 122 3.5 CONCLUSIONS 222
REFERENCES 223
4 PALLADIUM CATALYSIS FOR OXIDATIVE 1,2-DIFUNCTIONALIZATION OF ALKENES 2
29 BEATRICE JACQUES AND KILIAN MUNIZ
4.1 INTRODUCTION 119
4.2 PALLADIUM-CATALYZED L^-DIFUNCTIONALIZATION REACTIONS: HALOGENATION
220 4.3 AMINOHALOGENATION REACTIONS 222 4.4 DIALKOXYLATION 125
4.5 AMINOACETOXYLATION REACTIONS 227 4.6 DIAMINATION REACTIONS 232
4.7 CONCLUSION 234
REFERENCES 234
5 RHODIUM-CATALYZED C-H AMINATIONS 137 HELENE LEBEL 137 5.1 METAL
NITRENES FROM IMINOIODINANES 239 5.1.1 INTRAMOLECULAR C-H AMINATION 140
5.1.2 INTERMOLECULAR C-H AMINATIONS 244
5.1.3 MECHANISM OF C-H AMINATION USING HYPERVALENT IODINE REAGENTS 247
5.2 METAL NITRENES FROM N-TOSYLOXYCARBAMATES 249 REFERENCES 254
6 THE PALLADIUM-CATALYZED SYNTHESIS OF AROMATIC HETEROCYCLES 257
YINGDONG LU AND BRUCE A. ARNDTSEN
6.1 INTRODUCTION 257
6.2 PALLADIUM IR-LEWIS ACIDITY; INTRAMOLECULAR NUCLEOPHILIC ATTACK ON
UNSATURATED BONDS 259
IMAGE 4
VILI CONTENTS
6.2.1 ADDITION TO ALKYNES 259
6.2.2 HETEROATOM ADDITION TO ALKYNES WITH FUNCTIONALIZATION 264 6.2.3
HETEROATOM ADDITION TO ALLENES 268 6.2.4 HETEROATOM ADDITIONS TO ALKENES
272 6.3 PALLADIUM-CATALYZED CARBON-HETEROATOM BOND FORMING
REACTIONS 274
6.3.1 PALLADIUM-CATALYZED CARBON-NITROGEN BOND FORMATION 274 6.3.2
PALLADIUM-CATALYZED CARBON-OXYGEN BOND FORMATION 177 6.4
PALLADIUM-CATALYZED CARBON-HETEROATOM BOND FORMATION WITH ALKYNES 278
6.5 HECK CYDIZATIONS 282
6.6 PALLADIUM CATALYZED C-H BOND ACTIVATION 285 6.7 MULTICOMPONENT
COUPLING REACTIONS 289 6.8 SUMMARY AND OUTLOOK 194
REFERENCES 194
7 NEW REACTIONS OF COPPER ACETYLIDES: CATALYTIC DIPOLAR CYCLOADDITIONS
AND BEYOND 199 VALERY V. FOKIN 7.1 INTRODUCTION 299
7.2 AZIDE-ALKYNE CYCLOADDITION: BASICS 200 7.3 COPPER-CATALYZED
CYCLOADDITIONS 203 7.3.1 CATALYSTS AND IIGANDS 203
7.3.2 CUAAC WITH IN SITU GENERATED AZIDES 208 7.3.3 MECHANISTIC ASPECTS
OF THE CUAAC REACTION 208 7.3.4 REACTIONS OF SULFONYL AZIDES 225 7.3.5
SULFONYL TRIAZOLES AS STABLE CARBENE PRECURSORS 215
7.3.6 REACTIONS OF 1-IODOALKYNES 228 7.3.7 REACTIONS OF COPPER
ACETYLIDES WITH OTHER DIPOLES 220 REFERENCES 222
8 TRANSITION METAL-CATALYZED SYNTHESIS OF MONOCYCLIC FIVE-MEMBERED
AROMATIC HETEROCYCLES 227 ALEXANDER S. DUDNIK AND VLADIMIR CEVORGYAN 8.1
INTRODUCTION 227
8.2 MONOCYCLIC FIVE-MEMBERED HETEROCYCLES 228 8.2.1 FURANS 228
8.2.1.1 SYNTHESIS OF FURANS VIA CYCLOISOMERIZATION REACTIONS 228 8.2.1.2
SYNTHESIS OF FURANS VIA "3 + 2" CYCLOADDITION REACTIONS 264 8.2.2
PYRROLES 273
8.2.2.1 SYNTHESIS OF PYRROLES VIA CYCLOISOMERIZATION REACTIONS 273
8.2.2.2 SYNTHESIS OF PYRROLES VIA "4 + 1" CYCLOADDITION REACTIONS 283
8.2.2.3 SYNTHESIS OF PYRROLES VIA "3 + 2" CYDOADDITION REACTIONS 293
8.2.2.4 SYNTHESIS OF PYRROLES VIA "2 + 2 + 1" CYDOADDITION REACTIONS 298
IMAGE 5
CONTENTS IX
8.3 CONCLUSION 303
8.4 ABBREVIATIONS 308
REFERENCES 309
9 TRANSITION METAL-CATALYZED SYNTHESIS OF FUSED FIVE-MEMBERED AROMATIC
HETEROCYCLES 327 ALEXANDER S. DUDNIK AND VLADIMIR CEVORGYAN 9.1
INTRODUCTION 327
9.2 FUSED FIVE-MEMBERED HETEROCYCLES 328 9.2.1 BENZOFURANS 328
9.2.1.1 SYNTHESIS OF BENZOFURANS VIA CYCLOISOMERIZATION REACTIONS 328
9.2.1.2 SYNTHESIS OF BENZOFURANS VIA INTRAMOLECULAR ARYLATION REACTIONS
327 9.2.1.3 SYNTHESIS OF BENZOFURANS VIA "4 + 1" CYDOADDITION REACTIONS
329 9.2.1.4 SYNTHESIS OF BENZOFURANS VIA "3 + 2" CYDOADDITION REACTIONS
332
9.2.2 BENZOTHIOPHENES 333 9.2.2.1 SYNTHESIS OF BENZOTHIOPHENES VIA
CYCLOISOMERIZATION REACTIONS 334 9.2.2.2 SYNTHESIS OF BENZOTHIOPHENES
VIA "4 + 1" CYDOADDITION REACTIONS 337 9.2.2.3 SYNTHESIS OF
BENZOTHIOPHENES VIA "3 + 2" CYDOADDITION REACTIONS 338 9.2.3 INDOLES 339
9.2.3.1 SYNTHESIS OF INDOLES VIA CYCLOISOMERIZATION REACTIONS 340
9.2.3.2 SYNTHESIS OF INDOLES VIA INTRAMOLECULAR ARYLATION REACTIONS 362
9.2.3.3 SYNTHESIS OF INDOLES VIA "4 + 1" CYDOADDITION REACTIONS 368
9.2.3.4 SYNTHESIS OF INDOLES VIA "3 + 2" CYDOADDITION REACTIONS 373
9.2.4 ISOINDOLES 381
9.2.4.1 SYNTHESIS OF ISOINDOLES VIA CYCLOISOMERIZATION REACTIONS 382
9.2.4.2 SYNTHESIS OF ISOINDOLES VIA "4 + 1" CYDOADDITION REACTIONS 383
9.2.5 INDOLIZINES 383
9.2.5.1 SYNTHESIS OF INDOLIZINES VIA CYCLOISOMERIZATION REACTIONS 385
9.2.5.2 SYNTHESIS OF INDOLIZINES VIA "3 + 2" CYDOADDITION REACTIONS 396
9.3 CONCLUSION 399
9.4 ABBREVIATIONS 401
REFERENCES 402
10 CARBON-HETEROATOM BOND FORMATION BY RH'-CATALYZED RING-OPENING
REACTIONS 422 MATTHEWJ. FLEMING AND MARK TAUTENS 10.1 INTRODUCTION 422
10.2 RING-OPENING MESO-OXABICYCLIC ALKENES WITH OXYGEN-BASED
NUCLEOPHILES 422 10.3 RING-OPENING MESO-OXABICYDIC ALKENES WITH
NITROGEN-BASED NUCLEOPHILES 427
10.4 RING-OPENING MESO-AZABICYCLIC ALKENES WITH NITROGEN-BASED
NUCLEOPHILES 419 10.5 RING-OPENING MESO-OXABICYCLIC ALKENES WITH
SULFUR-BASED NUCLEOPHILES 423
IMAGE 6
CONTENTS
10.6 MECHANISTIC MODEL 424
10.7 RING-OPENING UNSYMMETRICAL OXA- AND AZA-BICYDIC ALKENES WITH
HETEROATOM NUCLEOPHILES 427 10.8 RING-OPENING OF VINYL EPOXIDES WITH
HETEROATOM NUDEOPHILES 432 10.9 CONCLUSION 434
REFERENCES 435
11 COLD-CATALYZED ADDITION OF NITROGEN AND SULFUR NUCLEOPHILES TO C-C
MULTIPLE BONDS 437 ROSS A. WIDENHOEFER AND FEIJIE SONG
11.1 INTRODUCTION 437 11.2 ADDITION OF NITROGEN NUCLEOPHILES TO ALKYNES
437 11.2.1 HYDROAMINATION 437 11.2.1.1 INTRAMOLECULAR PROCESSES 437
11.2.1.2 INTERMOLECULAR PROCESSES 440 11.2.2 ACETYLENIC SCHMIDT REACTION
442 11.2.3 TANDEM C-N/C-C BOND FORMING PROCESSES 442 11.2.4 TANDEM
C-N/C-X BOND FORMING PROCESSES 446
11.3 HYDROAMINATION OF ALIENES 448 11.3.1 INTRAMOLECULAR PROCESSES 448
11.3.2 INTERMOLECULAR PROCESSES 449 11.3.3 ENANTIOSELECTIVE PROCESSES
451 11.4 HYDROAMINATION OF ALKENES AND DIENES 453 11.4.1 UNACTIVATED
ALKENES 453 11.4.1.1 SULFONAMIDES AS NUCLEOPHILES 453 11.4.1.2
CARBOXAMIDE DERIVATIVES AS NUDEOPHILES 454 11.4.1.3 AMMONIUM SALTS AS
NUCLEOPHILES 455 11.4.2 METHYLENECYCLOPROPANES, VINYLCYDOPROPANES, AND
DIENES 456 11.5 ADDITION OF SULFUR NUCLEOPHILES TO C-C MULTIPLE BONDS
457 11.5.1 ALKYNES 457 11.5.2 ALIENES AND DIENES 458
REFERENCES 459
12 GOLD-CATALYZED ADDITION OF OXYGEN NUCLEOPHILES TO C-C MULTIPLE BONDS
463 ROSS A. WIDENHOEFER AND FEIJIE SONG
12.1 INTRODUCTION 463 12.2 ADDITION TO ALKYNES 464 12.2.1 CARBINOLS AS
NUCLEOPHILES 464 12.2.1.1 INTERMOLECULAR PROCESSES 464 12.2.1.2
INTRAMOLECULAR PROCESSES 465 12.2.1.3 TANDEM C-O/C-C BOND FORMING
PROCESSES 466 12.2.2 KETONES AS NUCLEOPHILES 467 12.2.3 ALDEHYDES AS
NUCLEOPHILES 469 12.2.4 CARBOXYLIC ACIDS AS NUCLEOPHILES 471
IMAGE 7
CONTENTS XI
12.2.5 REARRANGEMENTS OF PROPARGYLIC CARBOXYLATES 472
12.2.5.1 ACYL MIGRATION FOLLOWED BY NUCLEOPHILC ATTACK 472 12.2.5.2 ACYL
MIGRATION FOLLOWED BY C=C/CSC ADDITION 473 12.2.5.3 ACYL MIGRATION
LEADING TO DIENE/KETONE FORMATION 474 12.2.6 CARBONATES AND CARBAMATES
AS NUCLEOPHILES 475 12.2.7 ETHERS AND EPOXIDES AS NUCLEOPHILES 476
12.2.8 ADDITIONAL NUCLEOPHILES 477 12.3 ADDITION TO ALLENES 478
12.3.1 CARBINOLS AS NUCLEOPHILES 478 12.3.1.1 INTRAMOLECULAR PROCESSES
478 12.3.1.2 ENANTIOSELECTIVE PROCESSES 480 12.3.1.3 INTERMOLECULAR
PROCESSES 482
12.3.2 KETONES AS NUCLEOPHILES 483 12.3.3 CARBOXYLIC ACID DERIVATIVES AS
NUCLEOPHILES 484 12 A ADDITION TO ALKENES 485
12.4.1 ALKENES AND DIENES 485 12.4.2 CYCLIZATION/NUDEOPHILE CAPTURE OF
ENYNES 487 REFERENCES 488
INDEX 493 |
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| id | DE-604.BV036763831 |
| illustrated | Illustrated |
| indexdate | 2024-07-20T10:51:16Z |
| institution | BVB |
| isbn | 9783527324286 |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-020680811 |
| oclc_num | 682148252 |
| open_access_boolean | |
| owner | DE-92 DE-11 DE-83 DE-29T DE-91G DE-BY-TUM DE-188 |
| owner_facet | DE-92 DE-11 DE-83 DE-29T DE-91G DE-BY-TUM DE-188 |
| physical | XVIII, 505 S. graph. Darst. |
| publishDate | 2011 |
| publishDateSearch | 2011 |
| publishDateSort | 2011 |
| publisher | Wiley-VCH |
| record_format | marc |
| spelling | Catalyzed carbon-heteroatom bond formation ed. by Andrei K. Yudin Weinheim Wiley-VCH 2011 XVIII, 505 S. graph. Darst. txt rdacontent n rdamedia nc rdacarrier Organische Synthese (DE-588)4075695-6 gnd rswk-swf Katalyse (DE-588)4029921-1 gnd rswk-swf Metallorganische Verbindungen (DE-588)4038906-6 gnd rswk-swf Kupplungsreaktion (DE-588)4166199-0 gnd rswk-swf Kupplungsreaktion (DE-588)4166199-0 s Katalyse (DE-588)4029921-1 s Metallorganische Verbindungen (DE-588)4038906-6 s DE-604 Organische Synthese (DE-588)4075695-6 s b DE-604 Yudin, Andrei K. Sonstige (DE-588)131679457 oth text/html http://deposit.dnb.de/cgi-bin/dokserv?id=3443172&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=020680811&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Catalyzed carbon-heteroatom bond formation Organische Synthese (DE-588)4075695-6 gnd Katalyse (DE-588)4029921-1 gnd Metallorganische Verbindungen (DE-588)4038906-6 gnd Kupplungsreaktion (DE-588)4166199-0 gnd |
| subject_GND | (DE-588)4075695-6 (DE-588)4029921-1 (DE-588)4038906-6 (DE-588)4166199-0 |
| title | Catalyzed carbon-heteroatom bond formation |
| title_auth | Catalyzed carbon-heteroatom bond formation |
| title_exact_search | Catalyzed carbon-heteroatom bond formation |
| title_full | Catalyzed carbon-heteroatom bond formation ed. by Andrei K. Yudin |
| title_fullStr | Catalyzed carbon-heteroatom bond formation ed. by Andrei K. Yudin |
| title_full_unstemmed | Catalyzed carbon-heteroatom bond formation ed. by Andrei K. Yudin |
| title_short | Catalyzed carbon-heteroatom bond formation |
| title_sort | catalyzed carbon heteroatom bond formation |
| topic | Organische Synthese (DE-588)4075695-6 gnd Katalyse (DE-588)4029921-1 gnd Metallorganische Verbindungen (DE-588)4038906-6 gnd Kupplungsreaktion (DE-588)4166199-0 gnd |
| topic_facet | Organische Synthese Katalyse Metallorganische Verbindungen Kupplungsreaktion |
| url | http://deposit.dnb.de/cgi-bin/dokserv?id=3443172&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=020680811&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT yudinandreik catalyzedcarbonheteroatombondformation |