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ОбложкаGold catalysis: an homogeneous approach / ed. by F.Dean Toste, V.Michelet. - London: Imperial College Press, 2014. - xvii, 545 p.: ill. - (Catalytic science series; vol.13). - Bibliogr. at the end of the chapters. - Ind.: p.537-545. - ISBN 978-1-84816-852-7
Шифр: (И/Г2-G60) 02
 

Место хранения: 02 | Отделение ГПНТБ СО РАН | Новосибирск

Оглавление / Contents
 
Contributors ................................................. xiii

Chapter 1  From Gold in Nature to Gold Catalysts ................ 1
Søren Kramer and Fahim Gagosz
1.1  The Gold Element: An Overview .............................. 1
     1.1.1  History of gold ..................................... 1
     1.1.2  Abundance, production, and stocks ................... 2
     1.1.3  Demand and supply ................................... 3
     1.1.4  Price ............................................... 3
     1.1.5  General physical and chemical properties ............ 4
     1.1.6  Applications ........................................ 4
1.2  History of Homogeneous Gold Catalysis ...................... 5
1.3  General Reactivity of Electrophilic Gold Species ........... 9
1.4  Gold Catalysts ............................................ 14
     1.4.1  Inorganic gold catalysts ........................... 16
     1.4.2  Gold complexes ..................................... 19
     1.4.3  Chiral catalysts ................................... 34
1.5  Conclusion ................................................ 38
     References ................................................ 40

Chapter 2  Homogeneous Gold-Catalyzed Oxidation and
Reduction Reactions ............................................ 51
Liming Zhang
2.1  Introduction .............................................. 51
2.2  Homogeneous Gold-Catalyzed Oxidation Reactions
     with External Oxidants .................................... 52
     2.2.1  Alkyne or allene as substrate ...................... 52
     2.2.2  Alkenes as substrates .............................. 67
     2.2.3  Alcohol and sulfides as substrates ................. 71
2.3  Homogeneous Gold-Catalyzed Intramolecular
     Redox Reactions ........................................... 71
     2.3.1  With tether oxidants ............................... 71
     2.3.2  Involving hydride migration ........................ 77
2.4  Homogeneous Gold-Catalyzed Reductions ..................... 79
2.5  Summary ................................................... 80
2.6  Acknowledgment ............................................ 80
     References ................................................ 81

Chapter 3  Gold-Catalyzed Addition of Carbon Nucleophiles to
C-C Multiple Bonds, Carbonyls, and other Electrophiles ......... 87
Bryon L. Simmons and Hong C. Shen
3.1  Introduction .............................................. 87
3.2  Addition of Carbon Nucleophiles to Alkynes ................ 88
     3.2.1  Addition of enols, silyl enol ethers, and silyl
            ketene amides to alkynes ........................... 88
     3.2.2  Addition of enamine derivatives to alkynes ......... 92
     3.2.3  Addition of arenes to alkynes ...................... 93
     3.2.4  Addition of alkenes to alkynes ..................... 99
     3.2.5  Addition of allyls to C-C multiple bonds .......... 104
     3.2.6  Addition of allenes to alkynes .................... 107
     3.2.7  Addition of carbenes to alkynes ................... 108
3.3  Addition of Carbon Nucleophiles to Allenes ............... 108
3.4  Addition of Carbon Nucleophiles to Alkenes ............... 114
3.5  Addition of Carbon Nucleophiles to Carbonyls ............. 119
3.6  Addition of Carbon Nucleophiles to Iminiums .............. 122
3.7  Addition of Arenes and Alkenes to Miscellaneous
     Electrophiles ............................................ 122
3.8  Conclusion ............................................... 129
     References ............................................... 130

Chapter 4  Gold-Catalyzed Addition of Heteroatom Nucleophile
to C-C Multiple Bond .......................................... 137
Naoki Asao, Naoya Hatakeyama and Yoshinori Yamamoto
4.1  Introduction ............................................. 137
4.2  Nitrogen Nucleophiles .................................... 137
     4.2.1  Addition to alkynes ............................... 137
     4.2.2  Addition to allenes ............................... 141
     4.2.3  Addition to alkenes and dienes .................... 143
4.3  Oxygen Nucleophiles ...................................... 145
     4.3.1  Addition to alkynes ............................... 145
     4.3.2  Addition to allenes ............................... 161
     4.3.3  Addition to alkenes and dienes .................... 162
4.4  Sulfur Nucleophiles ...................................... 164
4.5  Other Heteroatom Nucleophiles ............................ 165
4.6  Conclusion ............................................... 166
     References ............................................... 166

Chapter 5  Gold-Catalyzed Synthesis of Heterocycles ........... 175
Antonio Arcadi
5.1  Introduction ............................................. 175
5.2  Synthesis of Heterocycles via Gold-Catalyzed Heteroatom
     Addition to Unsaturated C-C Bonds ........................ 176
     5.2.1  Synthesis of heterocyclic compounds through
            intermolecular hydrofunctionalization of alkynes .. 177
     5.2.2  Synthesis of heterocyclic compounds through
            intramolecular hydrofunctionalization of
            alkynes, allenes, and alkenes ..................... 180
     5.2.3  Heterocyclization of alkynes tethered with
            carbonyl groups ................................... 188
     5.2.4  Gold-catalyzed migratory cyclizations ............. 191
5.3  Synthesis of Heterocyclic Derivatives through
     Gold-Catalyzed Cyclization of Polyunsaturated Compounds .. 193
5.4  Synthesis of Heterocyclic Compounds via oc-Oxo Gold
     Carbenoid ................................................ 196
5.5  Synthesis of Heterocyclic Derivatives through Gold-
     Catalyzed Cycloaddition Reactions ........................ 201
5.6  Synthesis of Heterocyclic Derivatives through Gold-
     Catalyzed Activation of Carbonyl Groups and Alcohols ..... 203
5.7  Synthesis of Heterocyclic Compounds through Gold-
     Mediated C-H Bond Functionalization ...................... 206
     5.7.1  Direct C-H functionalization of heterocycles ...... 206
     5.7.2  Intramolecular gold-catalyzed hydroarylation
            reactions ......................................... 208
     5.7.3  Alkyne C-H and С 3-H functionalization ............ 211
5.8  Gold-Catalyzed Domino Cyclization/Oxidative Coupling
     Reactions ................................................ 212
5.9  Conclusions .............................................. 215
     References ............................................... 217

Chapter 6  Gold-Catalyzed Multi-Component Reactions ........... 225
Rachid Skouta and Chao-Jun Li
6.1  Introduction ............................................. 225
6.2  Gold-Catalyzed Three-Component Reactions ................. 226
     6.2.1  Aldehydes, terminal alkynes, and amines ........... 226
     6.2.2  Aldehydes, terminal alkynes, and
            triethylorthoformate .............................. 234
     6.2.3  Aldehydes, ketones, and carbamates ................ 234
     6.2.4  Imines, acyl chlorides, and terminal alkynes ...... 236
     6.2.5  Acetylenedicarboxylates, quinoline/isoquinoline,
            and terminal alkynes .............................. 237
     6.2.6  (Arylmethylene)cyclopropylcarbinols, terminal
            alkynes, and alcohols ............................. 239
     6.2.7  Amines, internal alkynes, and terminal alkynes .... 240
     6.2.8  Alkenes, boronic acid, and oxygen nucleophiles .... 242
6.3  Gold-Catalyzed Three-Component Reactions/Tandem
     Cyclization .............................................. 243
     6.3.1  Aldehydes, terminal alkynes, and amines/
            Cycloisomerization ................................ 243
     6.3.2  Glyoxylic acid, alkynes, and amines/
            Intramolecular cyclization ........................ 244
     6.3.3  Enantioselective [4 + 2] cycloaddition/
            Intramolecular hydroamination ..................... 246
6.4  Concluding Remarks ....................................... 247
6.5  Acknowledgments .......................................... 247
     References ............................................... 248

Chapter 7  Gold Catalysis on Tandem and Cascade Reactions ..... 253
Rai-Shung Liu
7.1  Introduction ............................................. 253
7.2  Oxo Alkynes .............................................. 254
7.3  Oxodienes ................................................ 263
7.4  Iminoalkynes ............................................. 266
7.5  Aminoalkynes ............................................. 266
7.6  Nitroalkyne .............................................. 266
7.7  Alkynyl Nitrone .......................................... 267
7.8  Allenyl Acetals .......................................... 268
7.9  Epoxyalkynes ............................................. 269
7.10 Alkynyl Hydroxylamine .................................... 270
7.11 Conclusion ............................................... 271
     References ............................................... 271

Chapter 8  Cycloisomerization Reactions of 1, N-Enynes ........ 275
Nuria Huguet and Antonio M. Echavarren
8.1  Introduction ............................................. 275
8.2  Gold Complexes ........................................... 275
8.3  Gold-Catalyzed Cyclization of 1, n-Enynes ................ 278
     8.3.1  Gold-catalyzed cycloisomerizations of
            1,6-enynes ........................................ 278
     8.3.2  Gold-catalyzed cycloisomerizations and skeletal
            rearrangement of 1, 5-enynes ...................... 293
     8.3.3  Gold-catalyzed cycloisomerizations and skeletal
            rearrangement of 1, n-enynes (n > 6) .............. 309
     8.3.4  Intermolecular reactions of alkynes with alkenes
            and [2 + 2] cycloadditions ........................ 311
     References ............................................... 314

Chapter 9  Gold-Catalyzed Reactions of Propargylic Esters ..... 331
Louis Fensterbank, Jean-Philippe Goddard, Max Malacria and
Antoine Simonneau
9.1  Introduction ............................................. 331
9.2  1,2-O-Acyl Migrations .................................... 335
     9.2.1  Scope and applications ............................ 335
     9.2.2  Intermolecular processes .......................... 343
9.3  1,3-O-Acyl Migrations .................................... 345
     9.3.1  Intramolecular nucleophilic additions onto the
            gold-activated allenyl ester ...................... 346
     9.3.2  Allenyl esters as nucleophiles in allenyne
            systems ........................................... 355
     9.3.3  Cycloadditions and electrocyclizations ............ 362
     9.3.4  Access to unsaturated carbonyl derivatives from
            propargylic esters ................................ 372
     9.3.5  Access to (1,3)-dienes from propargylic esters .... 376
9.4  Conclusion ............................................... 380
     References ............................................... 381

Chapter 10  Gold-Catalyzed Cross-Coupling Reactions ........... 393
Suzanne A. Blum
10.1 Introduction ............................................. 393
10.2 Dual-Catalytic Gold and Palladium Cross-Coupling
     Reactions ................................................ 394
     10.2.1 Mechanistic reaction design considerations ........ 394
     10.2.2 Simultaneous activation: Gold-catalyzed
            cyclization initiates oxidative addition of
            palladium ......................................... 395
     10.2.3 Tandem reactivity: Sonogashira-type cross-
            couplings with gold and palladium ................. 399
10.3 Fundamental Understanding through Stoichiometric
     Experiments .............................................. 401
     10.3.1 Palladium-catalyzed cross-coupling
            of stoichiometric organogold reagents ............. 402
     10.3.2 Mechanism: Single-step transmetalation ............ 405
     10.3.3 Other metals ...................................... 406
10.4 Challenges ............................................... 408
     10.4.1 Gold redox reactivity ............................. 408
     10.4.2 Dual-catalytic turnover strategies ................ 409
10.5 Outlook .................................................. 409
     References ............................................... 410

Chapter 11  Gold-Catalyzed Reactions: A Computational
Approach ...................................................... 413
Elena Soriano and Jose Marco-Contelles
11.1 Introduction ............................................. 413
11.2 Theoretical Considerations ............................... 415
     11.2.1 Relativistic effects .............................. 415
     11.2.2 Structure and bonding properties of the
            reactant complexes ................................ 418
11.3 Mechanistic Considerations ............................... 428
     11.3.1 Alkyne activation and reactivity .................. 428
     11.3.2 Key intermediates: Carbene or carbocation ......... 430
     11.3.3 Other mechanistic considerations .................. 436
11.4 Acknowledgment ........................................... 438
     References ............................................... 438

Chapter 12  Recent Developments in Asymmetric Catalysis ....... 445
Patrick Y. Toullec, Alexandre Pradal and Véronique Michelet
12.1 Reactivity of Carbonyl- and Imine-Functionalized
     Derivatives .............................................. 448
12.2 Reactivity of Functionalized Alkenes ..................... 454
     12.2.1 Hydrogenation and protonation reactions ........... 454
     12.2.2 Nucleophilic additions to alkenes or alkenyl
            intermediates ..................................... 455
12.3 Gold-Catalyzed Activation of Allenes ..................... 460
     12.3.1 Enantioselective addition of oxygen nucleophiles
            to allenes ........................................ 460
     12.3.2 Enantioselective addition of nitrogen
            nucleophiles to allenes ........................... 463
     12.3.3 Enantioselective addition of carbon nucleophiles
            to allenes ........................................ 467
12.4 Gold-Catalyzed Activation of Alkynes ..................... 472
     12.4.1 Rearrangement of propargylic esters and
            reactivity of carbenoid intermediates ............. 472
     12.4.2 Addition of carbon or heteroatom to alkynes ....... 477
     12.4.3 Cycloisomerization reactions of enynes ............ 482
12.5 Conclusion ............................................... 492
     References ............................................... 493

Chapter 13 Gold Catalysis in Natural Product Synthesis ........ 501
Michael R. Gesinski and F. Dean Toste
13.1 Introduction ............................................. 501
13.2 Addition of Heteroatoms .................................. 502
     13.2.1 Hydration of alkynes: Synthesis of ketones ........ 502
     13.2.2 Intramolecular hydroalkoxylations ................. 504
     13.2.3 Spiroketalization ................................. 508
     13.2.4 Cyclization via pyrylium intermediates ............ 511
     13.2.5 1,2- and 1,3-Acyl migration ....................... 512
     13.2.6 Hydrocarboxylation ................................ 516
     13.2.7 Hydroamination .................................... 518
     13.2.8 Rearrangements of N-Oxides ........................ 521
13.3 Enyne Cyclizations ....................................... 523
     13.3.1 The Conia-ene reaction ............................ 523
     13.3.2 Enyne-pinacol cascade reactions ................... 525
     13.3.3 Formal [2 + 2 + 2] enyne/carbonyl cycloadditions .. 526
     13.3.4 Other cascade reactions ........................... 526
13.4 Hydroarylation Reactions ................................. 528
13.5 Aldol Reactions .......................................... 530
13.6 Conclusion ............................................... 531
     References ............................................... 532

Index ......................................................... 537

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