Metal-catalyzed cross-coupling reactions and more:
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| 245 | 1 | 0 | |a Metal-catalyzed cross-coupling reactions and more |c ed. by Armin de Meijere ... |
| 264 | 1 | |a Weinheim |b Wiley-VCH | |
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CONTENTS TO VOLUME 1
PREFACE XV
LIST OF CONTRIBUTORS XVII
1 MECHANISTIC ASPECTS OF METAL-CATALYZED C,C- AND C,X-BOND FORMING
REACTIONS 1
ANTONIO M. ECHAVARREN AND ANNA HOMS
1.1 MECHANISMS OF CROSS-COUPLING REACTIONS 1
1.1.1 THE EARLIER MECHANISTIC PROPOSAL: THE STILLE REACTION 2
1.1.2 THE OXIDATIVE ADDITION 3
1.1.2.1 CIS-COMPLEXES IN THE OXIDATIVE ADDITION 4
1.1.2.2 THE ROLE OF ALKENE AND ANIONIC LIGANDS 5
1.1.2.3 CROSS-COUPLINGS IN THE PRESENCE OF BULKY PHOSPHINES 6
1.1.2.4 N-HETEROCYCLIC CARBENES AS LIGANDS 12
1.1.2.5 PALLADACYDES AS CATALYSTS 13
1.1.2.6 INVOLVEMENT OF PD(IV) IN CATALYTIC CYCLES 14
1.1.2.7 OXIDATIVE ADDITION OF STANNANES TO PD(0) 16
1.1.3 THE TRANSMETALLATION IN THE STILLE REACTION 16
1.1.3.1 ISOLATION OF THE TRANSMETALLATION STEP 16
1.1.3.2 DISSOCIATIVE MECHANISTIC PROPOSALS 18
1.1.3.3 CYCLIC AND OPEN ASSOCIATIVE TRANSMETALLATION 19
1.1.3.4 THE COPPER EFFECT 23
1.1.3.5 TRANSMETALLATION IN THE SUZUKI-MIYAURA REACTION 24
1.1.3.6 TRANSMETALLATION IN THE NEGISHI REACTION 27
1.1.3.7 TRANSMETALLATION IN THE HIYAMA REACTION 28
1.1.3.8 COUPLINGS CATALYZED BY COPPER AND GOLD 30
1.1.3.9 COUPLINGS CATALYZED BY IRON AND COBALT 32
1.1.4 REDUCTIVE ELIMINATION 33
1.2 PALLADIUM-CATALYZED A-ARYLATION OF CARBONYL COMPOUNDS AND
NITRILES 35
1.3 FORMATION OF C-X (X = N, O, S) BONDS IN METAL-CATALYZED
REACTIONS 36
HTTP://D-NB.INFO/1034510851
VI | CONTENTS
1.3.1 REDUCTIVE ELIMINATION TO GENERATE C-N, C-O, AND C-S BONDS FROM *
ORGANOPALLADIUM(II) COMPLEXES 39
1.3.2 NICKEL- AND COPPER-CATALYZED FORMATION OF C-X BONDS 44
1.4 SUMMARY AND OUTLOOK 46
LIST OF ABBREVIATIONS 46
REFERENCES 47
2 STATE-OF-THE-ART IN METAL-CATALYZED CROSS-COUPLING REACTIONS OF
ORGANOBORON COMPOUNDS WITH ORGANIC ELECTROPHILES 65
JACK C.H. LEE AND DENNIS G. HALL
2.1 INTRODUCTION 66
2.1.1 CATALYTIC CYCLE 66
2.1.2 IMPROVEMENTS TOWARD MORE EFFICIENT CROSS-COUPLING CONDITIONS 69
2.1.2.1 DEVELOPMENT OF NEW PHOSPHINE AND NHC LIGANDS 69
2.1.2.2 USAGE OF MASKED BORON DERIVATIVES AS CROSS-COUPLING PARTNERS 70
2.1.2.3 LEWIS ACIDS AS ADDITIVES 72
2.1.2.4 ADJUSTING THE NUDEOPHILICITY OF ORGANOBORON CROSS-COUPLING
PARTNERS 73
2.1.2.5 COPPER SALTS AS ADDITIVES 74
2.2 ADVANCES IN CROSS-COUPLING REACTIONS FOR THE FORMATION OF
C(SP
2
)-C(SP
2
) BONDS 75
2.2.1 BACKGROUND 75
2.2.2 RECENT DEVELOPMENTS IN THE USE OF NEW ELECTROPHILIC COUPLING
PARTNERS 75
2.2.2.1 CHLORIDES 75
2.2.2.2 FLUORIDES 79
2.2.2.3 PSEUDOHALIDES 82
2.2.3 RECENT DEVELOPMENTS IN ORGANOBORON CROSS-COUPLING PARTNERS 92
2.2.3.1 TRIFLUOROBORATE SALTS 93
2.2.3.2 N-METHYLIMINODIACETIC ACID (MIDA) BORONATES 97
2.2.3.3 OTHER ORGANOBORON CROSS-COUPLING PARTNERS 99
2.2.4 SYNTHESIS OF ENANTIOMERICALLY ENRICHED ATROPISOMERS 101
2.3 ADVANCES IN THE CROSS-COUPLING REACTIONS FOR THE FORMATION OF
C(SP
3
)-C(SP
2
) OR C(SP
3
)-C(SP
3
) BONDS 103
2.3.1 BACKGROUND 103
2.3.1.1 STEREOCHEMISTRY 104
2.3.2 CROSS-COUPLINGS BETWEEN UNSATURATED SP
2
CARBON CENTERS AND SP
3
CARBON CENTERS 105
2.3.2.1 CROSS-COUPLINGS BETWEEN SP
3
ALKYL HALIDES AND SP
2
ALKENYL OR ARYL
BORON DERIVATIVES 105
2.3.2.2 CROSS-COUPLINGS BETWEEN SP
3
ALKYL BORON DERIVATIVES WITH SP
2
ALKENYL
OR ARYL HALIDES 110
2.3.3 CROSS-COUPLINGS BETWEEN SP
3
CARBON CENTERS WITH SP
3
CARBON
CENTERS 117
2.3.3.1 CROSS-COUPLINGS BETWEEN ACHIRAL SUBSTRATES 117
CONTENTS IVII
2.3.3.2 STEREOSELECTIVE CROSS-COUPLING REACTIONS OF SP
3
ALKYL HALIDES WITH SP
3
ALKYLBORANES 118
2.4 EXPERIMENTAL PROCEDURES 121
2.4.1 2,6-DIMETHOXY-2',6'-DIMETHYLBIPHENYL (55) 121
2.4.2 4-METHOXYBIPHENYL (R = C(0)NET2, R' = H, AR =
4-METHOXYPHENYL) 121
2.4.3 1-PHENYLNAPHTHALENE (ROH = NAPHTHOL, AR = PH) 122
2.4.4 L-(3,5-DIMETHOXYPHENYL)-5-PHENYLPENTAN-3-ONE (RAIKYI-BFJK = 197,
R
1
= CH2CH2PI1, R' = 3,5-DIMETHOXYBENZENE) 122
2.4.5 L-PHENYL-L-(4-ACETYLPHENYL-ETHANE (ARL = 4-IODOACETOPHENONE) 122
2.4.6 NAPHTHALENE-L,8-DIAMIDO (DAN) DERIVATIVE (AR = PH) 123
2.4.7 2-METHYL-5-PHENYLPENTYL BENZYL(PHENYL)CARBAMATE (R
A
LKYI = ME,
X = BR, R'AIKYI
= CH
2
CH
2
CH
2
PH) 123
2.5 SUMMARY AND OUTLOOK 124
REFERENCES 124
3 PD-CATALYZED CROSS-COUPLING WITH ORGANOMETALS CONTAINING ZN, AL, ZR,
AND SO ON - THE NEGISHI COUPLING AND ITS RECENT ADVANCES 133
SHIQING XU, HIROFUMI KAMADA, EUN HOO KIM, AKIMICHI ODA, AND
EI-ICHI NEGISHI
3.1 BACKGROUND AND DISCOVERY 134
3.1.1 WHY METALS? WHY TRANSITION METALS? 134
3.1.2 WHY TRANSITION METAL-CATALYZED ORGANOMETALLIC REACTIONS? 136
3.2 DISCOVERY OF THE PD- OR NI-CATALYZED CROSS-COUPLING REACTIONS OF
ORGANOMETALS CONTAINING ZN, AL, ZR, AND B 137
3.3 THE CURRENT SCOPE OF THE PD- OR NI-CATALYZED CROSS-COUPLING AND ITS
APPLICATION TO THE SYNTHESIS OF NATURAL PRODUCTS AND OTHER COMPLEX
ORGANIC COMPOUNDS
154
3.3.1 CROSS-COUPLING BETWEEN TWO UNSATURATED (ARYL, ALKENYL, AND/OR
ALKYNYL) GROUPS 156
3.3.1.1 ARYL-ARYL COUPLING 156
3.3.1.2 ARYL-ALKENYL AND ALKENYL-ARYL COUPLINGS 158
3.3.1.3 ALKENYL-ALKENYL COUPLING 159
3.3.1.4 PD-CATALYZED ALKYNYLATION 191
3.3.2 CROSS-COUPLING INVOLVING ONE ALLYL, BENZYL, OR PROPARGYL GROUP 197
3.3.2.1 1,4-DIENES VIA PD-CATALYZED ALKENYL-ALLYL AND ALLYL-ALKENYL
COUPLING
AND 1,4-ENYNES BY PD-CATALYZED ALKYNYL-ALLYL COUPLING 197
3.3.2.2 BENZYL-ARYL, ARYL-BENZYL COUPLING 203
3.3.2.3 ALLYLBENZENE DERIVATIVES VIA PD-CATALYZED ALKENYL-BENZYL
COUPLING
AND ARYL-ALLYL AND ALLYL-ARYL COUPLING 204
3.3.2.4 BENZYLATED ALKYNES VIA PD-CATALYZED ALKYNYL-BENZYL COUPLING AND
ARYL-PROPARGYL AS WELL AS PROPARGYL-ARYL COUPLING 204
3.3.2.5 1,4-DIYNES VIA ALKYNYL-PROPARGYL COUPLING 207
VIII
| CONTENTS
3.3.2.6 SYNTHESIS OF NATURAL PRODUCTS CONTAINING 1,4-DIENE AND ALLYLATED
ARENES BY PD-CATALYZED ALLYLATION, BENZYLATION, AND
PROPARGYLATION 208
3.3.3 CROSS-COUPLING BETWEEN TWO ALLYL, BENZYL, AND/OR PROPARGYL
GROUPS 210
3.3.3.1 1,5-DIENES AND 1,5-ENYNES VIA PD-CATALYZED CROSS-COUPLINGS WITH
ALLYL, BENZYL, PROPARGYL ELECTROPHILES 210
3.3.3.2 1,5-DIENES AND 1,5-ENYNES VIA PD-CATALYZED HOMOALLYL-ALKENYL
COUPLING AND HOMOPROPARGYL-ALKENYL COUPLING 212
3.3.3.3 BIBENZYLS, HOMOALLYLARENES, 1,5-DIENES, HOMOPROPARGYLARENES, AND
1,5-ENYNES VIA PD-CATALYZED NEGISHI COUPLING 214
3.3.4 CROSS-COUPLING INVOLVING ALKYLMETALS AND/OR ALKYL ELECTROPHILES
OTHER THAN THOSE CONTAINING ALLYL, BENZYL, AND/OR PROPARGYL
GROUPS 216
3.3.4.1 PD-CATALYZED ALKYL-ALKYL COUPLING 219
3.3.4.2 NI-CATALYZED ALKYL-ALKYL COUPLING 221
3.3.4.3 CATALYTIC ASYMMETRIC CROSS-COUPLING REACTIONS WITH SECONDARY
ALKYL
HALIDES 223
3.3.5 PD-CATALYZED ACYLATION, CYANATION, AND A-SUBSTITUTION OF ENOLATES
AND
RELATED DERIVATIVES 227
3.3.5.1 PD-CATALYZED ACYLATION 227
3.3.5.2 PD-CATALYZED CYANATION 232
3.3.5.3 PD-CATALYZED A-SUBSTITUTION OF ENOLATES AND RELATED DERIVATIVES
233
3.4 ZR-CATALYZED ASYMMETRIC CARBOALUMINATION OF ALKENES (ZACA)
ZACA-PD- OR CU-CATALYZED CROSS-COUPLING SEQUENTIAL PROCESSES AS A
GENERAL ROUTE TO ENANTIOMERICALLY ENRICHED CHIRAL ORGANIC
COMPOUNDS 243
3.4.1 ZIRCONIUM-CATALYZED ASYMMETRIC CARBOALUMINATION OF ALKENES
(ZACA REACTION) 243
3.4.1.1 HISTORICAL AND MECHANISTIC BACKGROUND OF CARBOMETALLATION OF
ALKENES AND ALKYNES WITH ALKYLZIRCONOCENE DERIVATIVES 244
3.4.1.2 CATALYTIC ASYMMETRIC CARBOMETALLATION OF ALKENES PROCEEDING VIA
DZHEMILEV ETHYLMAGNESIATIONS 246
3.4.2 * CURRENT SUMMARY OF DEVELOPMENT AND APPLICATION OF THE ZACA
REACTION AND CONCLUSION 249
3.4.2.1 ZACA-PD-CATALYZED CROSS-COUPLING SEQUENTIAL PROCESSES FOR THE
SYNTHESIS OF DEOXYPOLYPROPIONATES AND RELATED COMPOUNDS 249
3.4.2.2 ZACA-LIPASE-CATALYZED ACETYLATION-PD- OR CU-CATALYZED
CROSS-COUPLING SYNERGY TO CHIRAL ORGANIC COMPOUNDS 253
3.5 REPRESENTATIVE EXPERIMENTAL PROCEDURES 260
3.5.1 (2Z,4S)-5-(TERT-BUTYLDIMETHYLSILYLOXY)-2-PHENYL-4-METHYL-2-
PENTENE 260
3.5.2 (2Z,4,6)-ETHYL TRIDECA-2,4,6-TRIENOATE 260
3.5.3 (2Z)-2-ALLYL-3,7-DIMETHYLOCTA-2,6-DIEN-L-OL 260
3.5.4 ETHYL 2-(4-PHENYLBUTA-L,3-DIYNYL)BENZOATE 261
CONTENTS I IX
3.5.4.1 (E)
- L-CHLORO-4-PHENYL-1 -BUTEN-3 -YNE 261
3.5.4.2 ETHYL 2-(4-PHENYLBUTA-L,3-DIYNYL)BENZOATE 261
3.5.5 O- TERT-BUTYLDIPHENYLSILYL-PROTECTED
(3S,5)-3,9-DIMETHYL-6-ISOPROPYL-5,8-DECADIEN-L-OL 261
3.5.5.1 (L)-L-IODO-2-ISOPROPYL-5-METHYL-L,4-HEXADIENE 261
3.5.5.2 O-TERT-BUTYLDIPHENYLSILYL-PROTECTED
(3 S, 5 E)-3.9-DIMETHYL-6-ISOPROPYL-5,8-DECADIEN-1 -OL 262
3.5.6 1,3-DIPHENYLPROPYNE 262
3.5.7 (4S)-4-PHENYL-L-PENTENE 263
3.5.8 (J?)-2-PHENYLPROPAN-L-OL 263
ACKNOWLEDGMENTS 263
REFERENCES 264
4 CARBON-CARBON BOND FORMING REACTIONS MEDIATED BY ORGANOZINC
REAGENTS 279
FABRICE CHEMLA, FRANCK FERREIRA, OLIVIER JACKOWSKI, LAURENT MICOUIN, AND
ALEJANDRO PEREZ-LUNA
4.1 INTRODUCTION 279
4.2 METHODS OF PREPARATION OF ZINC ORGANOMETALLICS 280
4.2.1 DIRECT INSERTION OF ZN(0) INTO ORGANOHALIDES 280
4.2.2 TRANSMETALLATION REACTIONS 282
4.2.2.1 TRANSMETALLATION REACTIONS WITH MAIN-GROUP AND TRANSITION METAL
ORGANOMETALLICS 282
4.2.2.2 BORON-ZINC EXCHANGE REACTIONS 285
4.2.3 DIRECT ZINCATION REACTIONS 287
4.2.4 HALOGEN-ZINC EXCHANGE REACTIONS 288
4.2.5 HYDRO- AND CARBOZINCATION REACTIONS 290
4.3 UNCATALYZED CROSS-COUPLING REACTIONS OF ORGANOZINC REAGENTS 291
4.4 COPPER-CATALYZED CROSS-COUPLING REACTIONS OF ORGANOZINC
REAGENTS 293
4.4.1 CROSS-COUPLING WITH C(SP)- OR C(SP
2
)-ELECTROPHILES 293
4.4.2 CROSS-COUPLING REACTIONS WITH C(SP
3
)-ELECTROPHILES 295
4.5 TRANSITION-METAL-CATALYZED CROSS-COUPLING REACTIONS OF ORGANOZINC
REAGENTS 296
4.5.1 CROSS-COUPLING REACTIONS OF C(SP
2
)-ORGANOZINC REAGENTS 297
4.5.1.1 PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS 297
4.5.1.2 NICKEL-CATALYZED CROSS-COUPLING REACTIONS 311
4.5.1.3 RHODIUM-CATALYZED CROSS-COUPLING REACTIONS 315
4.5.1.4 COBALT-CATALYZED CROSS-COUPLING REACTIONS 316
4.5.1.5 IRON-CATALYZED CROSS-COUPLING REACTIONS 317
4.5.2 CROSS-COUPLING REACTIONS OF ALKYNYLZINC REAGENTS 318
4.5.2.1 CROSS-COUPLING WITH C(SP
2
)-ELECTROPHILES 318
4.5.2.2 CROSS-COUPLING WITH C(SP
3
)-ELECTROPHILES 320
4.5.3 CROSS-COUPLING REACTIONS OF C(SP
3
)-ORGANOZINC REAGENTS 321
4.5.3.1 PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS 322
X I CONTENTS
4.5.3.2 NICKEL-CATALYZED CROSS-COUPLING REACTIONS 332
4.5.3.3 PLATINUM-CATALYZED CROSS-COUPLING REACTIONS 342
4.5.3.4 IRON-CATALYZED CROSS-COUPLING REACTIONS 343
4.5.3.5 COBALT-CATALYZED CROSS-COUPLING REACTIONS 343
4.5.3.6 RHODIUM-CATALYZED CROSS-COUPLING REACTIONS 344
4.6 CONCLUSIONS 345
4.7 EXPERIMENTAL PROCEDURES 345
4.7.1 3-ETHOXYCARBONYLPHENYLZINC IODIDE (7) 345
4.7.2 6-CARBOETHOXY-3,5-DIMETHYLPYRIMIDINYL-5-ZINC CHLORIDE (27) 346
4.7.3 1-HEXENYLMETHYLZINC (37) 346
4.7.4 DI(5-CARBOETHOXY-5-HEXENYL)ZINC (39) 346
4.7.5 DI-(5-BROMO-2,4-DI(CARBOETHOXY)PHENYL)ZINC (60) 347
4.7.6 CYDOHEXYLISOPROPYLZINC (80) 347
4.7.7 10-NITRO-9-PHENYLDECYL ACETATE (126) 347
4.7.8 2-CYANO-2',4',6'-TRIISOPROPYLBIPHENYL (140) 348
4.7.9 (2R,3S)-2-(3,4-DIMETHOXYPHENYL)-8-MESITYL-5,7-DIMETHOXYCHROMAN-
3-OL (155) 348
4.7.10 2-(2-(THIOPHEN-2-YL)ETHYNYL)PYRIDINE (173) 349
4.7.11 6,6-DIETHOXY-2-PHENYL-L-HEXENE (231) 349
4.7.12 ETHYL 4'-METHOXY-BIPHENYL-3-CARBOXYLATE (244) 349
4.7.13 ETHYL 4-(FURAN-2-YL)BENZOATE (261) 350
4.7.14 TRIMETHYL((R)-3-P-TOLYLHEPT-L-YNYL)SILANE (268) 350
4.7.15 4-[2-(4-METHOXYPHENYL)PYRIMIDIN-4-YL]BENZONITRILE (286) 350
4.7.16 3-CYCLOHEPTYL-2-METHYLPROP-2-ENE (292) 351
4.7.17 ETHYL 4-(PHENYLETHYNYL)BENZOATE (301) 351
4.7.18 TERT-BUTYL((CIS-3-(4-((TERT-BUTYLDIMETHYLSILYL)OXY)BUT-L-YN-L-YL)
CYDOHEXYL)OXY)DIMETHYLSILANE (333) 351
4.7.19 CIS-TERT-BUTYL 2-(4-CYANOPHENYL)-4-PHENYLPIPERIDINE-L-CARBOXYLATE
(352) 352
4.7.20 L-(((E)-DODEC-4-ENYLOXY)METHYL)BENZENE (364) 352
4.7.21 ETHYL 6-PHENYLHEX-5-YNOATE (379) 352
4.7.22 8-OXO-8-PHENYLOCTYL PIVALATE (403) 353
4.7.23 7-PHENYLHEPTANOIC ACID DIETHYLAMIDE (441) 353
4.7.24 ETHYL 4-ISOPROPYLBENZOATE (456) 353
ACKNOWLEDGMENTS 354
LIST OF ABBREVIATIONS 354
REFERENCES 355
5 CARBON-CARBON-BOND-FORMING REACTIONS MEDIATED BY
ORGANOMAGNESIUM REAGENTS 365
FABRICS CHEMLA, FRANCK FERREIRA, ALEJANDRO PEREZ-LUNA, LAURENT MICOUIN,
AND OLIVIER JACKOWSKI
5.1 INTRODUCTION 365
5.2 METHODS OF PREPARATION OF MAGNESIUM ORGANOMETALLICS 366
5.2.1 DIRECT INSERTION OF MAGNESIUM 366
CONTENTS XI
5.2.2 HALOGEN-MAGNESIUM EXCHANGE REACTIONS 366
5.2.3 DIRECT MAGNESIATION REACTIONS 368
5.3 TRANSITION-METAL-CATALYZED CROSS-COUPLING REACTIONS OF
ORGANOMAGNESIUM REAGENTS 370
5.3.1 CROSS-COUPLING OF C(SP
2
)-ORGANOMAGNESIUM REAGENTS 372
5.3.1.1 NICKEL-CATALYZED CROSS-COUPLING REACTIONS 372
5.3.1.2 PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS 375
5.3.1.3 IRON-CATALYZED CROSS-COUPLING REACTIONS 379
5.3.1.4 COBALT-CATALYZED CROSS-COUPLING REACTIONS 383
5.3.1.5 MANGANESE-CATALYZED CROSS-COUPLING REACTIONS 383
5.3.1.6 RHODIUM-CATALYZED CROSS-COUPLING REACTIONS 383
5.3.2 CROSS-COUPLING REACTIONS OF C(SP)-ORGANOMAGNESIUM
REAGENTS 384
5.3.2.1 PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS 385
5.3.2.2 COBALT-CATALYZED CROSS-COUPLING REACTIONS 386
5.3.2.3 MANGANESE-CATALYZED OXIDATIVE CROSS-COUPLING REACTIONS 388
5.3.2.4 NICKEL-CATALYZED CROSS-COUPLING REACTIONS 389
5.3.3 CROSS-COUPLING REACTIONS OF C(SP
3
)-ORGANOMAGNESIUM
REAGENTS 390
5.3.3.1 NICKEL-CATALYZED CROSS-COUPLING REACTIONS 391
5.3.3.2 IRON-CATALYZED CROSS-COUPLING REACTIONS 398
5.3.3.3 PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS 404
5.3.3.4 COPPER-CATALYZED CROSS-COUPLING REACTIONS 406
5.3.3.5 COBALT-CATALYZED REACTIONS 408
5.3.3.6 MANGANESE-CATALYZED CROSS-COUPLING REACTIONS 410
5.3.3.7 SILVER-CATALYZED CROSS-COUPLING REACTIONS 410
5.4 CONCLUSIONS 411
5.5 EXPERIMENTAL PROCEDURES 411
5.5.1 ETHYL 3'-BROMO-4'-[(TERT-BUTOXYCARBONYL)OXY]BIPHENYL-4-
CARBOXYLATE (3) 411
5.5.2 (2-BROMOCYDOPENT-L-EN-L-YL)(CYCLOHEXYL)METHANOL (13) 412
5.5.3 DIETHYL 4-BROMO-6-IODOISOPHTHALATE (29) 412
5.5.4 4-METHOXYBIPHENYL (41) 413
5.5.5 2-PHENYL-(2'-PHENYL)-4-METHYLQUINOLINE (69) 413
5.5.6 9-METHYLENEPENTADEC-7-YNE (144) 414
5.5.7 TRIMETHYL(3-P-TOLYLPROP-1 -YNYL)SILANE (152) 414
5.5.8 L-(L-HEPTYNYL)-4-METHOXYBENZENE (155) 414
5.5.9 N,N-5-TRIMETHYLNAPHTHALEN-L-AMINE (174) 415
5.5.10 N,N-DIETHYLDECANAMIDE (200) 415
5.5.11 ()-12-ACETOXYDODEC-5-ENE (210) 415
5.5.12 2-TERT-BUTYL-4-TERT-PENTYL-6-PHENYL-L,3,5-TRIAZINE (254) 416
ACKNOWLEDGMENTS 416
LIST OF ABBREVIATIONS 416
REFERENCES 417
XIII CONTENTS
6 ORGANOTIN REAGENTS IN CROSS-COUPLING REACTIONS 423
BETTN MARTM-MATUTE, KDLMDN J. SZABO, AND TERENCE N. MITCHELL
6.1 INTRODUCTION 423
6.2 MECHANISM AND METHODOLOGY 424
6.2.1 MECHANISM 424
6.2.2 METHODOLOGY 428
6.2.2.1 REACTION MEDIUM 429
6.2.2.2 NEW LIGANDS, CATALYSTS, AND ADDITIVES 429
6.2.2.3 NEW ORGANIC AND ORGANOTIN COUPLING PARTNERS 434
6.2.2.4 POLYMER-SUPPORTED STILLE CHEMISTRY 435
6.2.2.5 OTHER ADVANCES IN METHODOLOGY 436
6.3 NATURAL PRODUCT SYNTHESIS 443
6.3.1 INTRAMOLECULAR COUPLINGS 444
6.3.2 INTERMOLECULAR COUPLINGS 446
6.3.2.1 VINYL-VINYL COUPLINGS 446
6.3.2.2 OTHER COUPLINGS INVOLVING VINYLTINS 448
6.3.2.3 COUPLINGS OF HETEROCYCLIC ORGANOTINS 449
6.3.2.4 OTHER INTERMOLECULAR COUPLINGS 449
6.4 ORGANIC SYNTHESIS 450
6.4.1 VINYL-VINYL COUPLINGS 450
6.4.2 OTHER COUPLINGS INVOLVING VINYLTINS 451
6.4.3 COUPLINGS OF ARYLTINS 454
6.4.4 COUPLINGS OF HETEROCYCLIC ORGANOTINS 455
6.4.5 COUPLINGS OF ALKYNYLTINS 456
6.4.6 COUPLINGS OF MISCELLANEOUS ORGANOTINS 457
6.5 POLYMER CHEMISTRY 457
6.5.1 MATERIALS BASED ON POLYTHIOPHENE (OR POLYSELENOPHENE)
BACKBONES 458
6.5.2 MATERIALS BASED ON THIOPHENE IN COMBINATION WITH OTHER REPEATING
UNITS 459
6.5.3 MATERIALS BASED ON PYRROLE AND FURAN 460
6.5.4 POLYPHENYLENEVINYLENE AND RELATED MATERIALS 460
6.5.5 OTHER MATERIALS 461
6.6 INORGANIC SYNTHESIS 461
6.6.1 COUPLINGS OF VINYLTINS 461
6.6.2 COUPLINGS OF ARYLTINS 462
6.6.3 COUPLINGS OF HETEROCYCLIC ORGANOTINS 462
6.6.4 COUPLINGS OF ALKYNYLTINS 462
6.7 CONCLUSIONS 463
6.8 EXPERIMENTAL PROCEDURES 464
6.8.1 SPIROCYCLIZATION BY GRIGG ET AL. 464
6.8.2 4,4-DICYANO-2,7-DIMETHYL-5-PHENYLOCTA-L,7-DIENE (R=ME) 464
6.8.3 4,4'-BIS[5-ETHYNYL(5'-METHYL-2,2'-BIPYRIDYL)]-L,L'-BIPHENYL 464
6.8.4 PENTACARBONYL[L-DIMETHYLAMINO-7-TRIMETHYLSILYL-2,4,6-
HEPTATRIYNYLIDENEJTUNGSTEN 465
LIST OF ABBREVIATIONS 465
REFERENCES 465
CONTENTS I XIII
CONTENTS TO VOLUME 2
LIST OF CONTRIBUTORS XIII
7 ORGANOSILICON COMPOUNDS IN CROSS-COUPLING REACTIONS 475
SCOTT E. DENMARK AND RAMZI F. SWEIS
8 CROSS-COUPLING OF ORGANYL HALIDES WITH ALKENES - THE HECK
REACTION 533
STEFAN BRASE AND ARMIN DE MEIJERE
9 CROSS-COUPLING REACTIONS TO SP CARBON ATOMS 665
TOBIAS A. SCHAUB AND MILAN KIVALA
10 CARBOMETALLATION REACTIONS 763
ILAN MAREK AND YURY MINKO
11 PALLADIUM-CATALYZED 1,4-ADDITIONS TO CONJUGATED DIENES 875
JAN-ERLING BACKVALL
12 CROSS-COUPLING REACTIONS VIA IT-ALLYLMETAL INTERMEDIATES 925
ANTON BAYER AND ULI KAZMAIER
CONTENTS TO VOLUME 3
LIST OF CONTRIBUTORS XIII
13 PALLADIUM-CATALYZED AROMATIC CARBON-NITROGEN BOND FORMATION 995
JAN PARODIES
14 THE DIRECTED ORTHO METALLATION (DOM)-CROSS-COUPLING NEXUS.
SYNTHETIC METHODOLOGY FOR THE FORMATION OF ARYL-ARYL AND
ARYL-HETEROATOM-ARYL
BONDS 1067
VICTOR SNIECKUS AND ERIC J.-G. ANCTIL
15 TRANSITION-METAL-CATALYZED HYDROAMINATION REACTIONS 1135
LAUREL L. SCHAFER, JACLCY C.-H. YIM, AND NEAL YONSON
16 OXIDATIVE FUNCTIONALIZATION OF ALKENES 1259
KILIAN MUNIZ AND CLAUDIO MARTINEZ
XIV
| CONTENTS
17 BIARYL SYNTHESIS THROUGH METAL-CATALYZED C-H ARYIATION 1315
JUNICHIRO YAMAGUCHI AND KENICHIRO ITAMI
18 C-H BOND ALKENYLATION 1389
TETSUYA SATOH AND MASAHIRO MIURA
19 C-H BOND ALKYLATION (INCLUDING HYDROARYLATION OF ALKENES) 1427
LUDIVINE JEAN-G6RARD, RODOLPHE JAZZAR, AND OLIVIER BAUDOIN
INDEX 1495 |
| any_adam_object | 1 |
| author2 | Meijere, Armin de |
| author2_role | edt |
| author2_variant | a d m ad adm |
| author_facet | Meijere, Armin de |
| building | Verbundindex |
| bvnumber | BV041591565 |
| classification_rvk | VH 9700 VK 5500 |
| classification_tum | CHE 622f |
| ctrlnum | (DE-599)DNB1034510851 |
| discipline | Chemie / Pharmazie Chemie |
| format | Book |
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| genre_facet | Aufsatzsammlung |
| id | DE-604.BV041591565 |
| illustrated | Not Illustrated |
| indexdate | 2024-08-03T01:13:07Z |
| institution | BVB |
| isbn | 3527331549 9783527331543 9783527655588 |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-027036629 |
| open_access_boolean | |
| physical | 240 mm x 170 mm |
| publishDateSort | 0000 |
| publisher | Wiley-VCH |
| record_format | marc |
| spelling | Metal-catalyzed cross-coupling reactions and more ed. by Armin de Meijere ... Weinheim Wiley-VCH 240 mm x 170 mm txt rdacontent n rdamedia nc rdacarrier Katalyse (DE-588)4029921-1 gnd rswk-swf Metallorganische Verbindungen (DE-588)4038906-6 gnd rswk-swf Metallorganische Chemie (DE-588)4602390-2 gnd rswk-swf Kreuzkupplungsreaktion (DE-588)1033635499 gnd rswk-swf (DE-588)4143413-4 Aufsatzsammlung gnd-content Metallorganische Chemie (DE-588)4602390-2 s DE-604 Metallorganische Verbindungen (DE-588)4038906-6 s Kreuzkupplungsreaktion (DE-588)1033635499 s Katalyse (DE-588)4029921-1 s Meijere, Armin de edt Erscheint auch als Online-Ausgabe, EPUB 978-3-527-65560-1 Erscheint auch als Online-Ausgabe, MOBI 978-3-527-65559-5 Erscheint auch als Online-Ausgabe, PDF 978-3-527-65561-8 text/html http://deposit.dnb.de/cgi-bin/dokserv?id=4329626&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=027036629&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Metal-catalyzed cross-coupling reactions and more Katalyse (DE-588)4029921-1 gnd Metallorganische Verbindungen (DE-588)4038906-6 gnd Metallorganische Chemie (DE-588)4602390-2 gnd Kreuzkupplungsreaktion (DE-588)1033635499 gnd |
| subject_GND | (DE-588)4029921-1 (DE-588)4038906-6 (DE-588)4602390-2 (DE-588)1033635499 (DE-588)4143413-4 |
| title | Metal-catalyzed cross-coupling reactions and more |
| title_auth | Metal-catalyzed cross-coupling reactions and more |
| title_exact_search | Metal-catalyzed cross-coupling reactions and more |
| title_full | Metal-catalyzed cross-coupling reactions and more ed. by Armin de Meijere ... |
| title_fullStr | Metal-catalyzed cross-coupling reactions and more ed. by Armin de Meijere ... |
| title_full_unstemmed | Metal-catalyzed cross-coupling reactions and more ed. by Armin de Meijere ... |
| title_short | Metal-catalyzed cross-coupling reactions and more |
| title_sort | metal catalyzed cross coupling reactions and more |
| topic | Katalyse (DE-588)4029921-1 gnd Metallorganische Verbindungen (DE-588)4038906-6 gnd Metallorganische Chemie (DE-588)4602390-2 gnd Kreuzkupplungsreaktion (DE-588)1033635499 gnd |
| topic_facet | Katalyse Metallorganische Verbindungen Metallorganische Chemie Kreuzkupplungsreaktion Aufsatzsammlung |
| url | http://deposit.dnb.de/cgi-bin/dokserv?id=4329626&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=027036629&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT meijerearminde metalcatalyzedcrosscouplingreactionsandmore |