Transition-Metal-Mediated Aromatic Ring Construction

Transition-Metal-Mediated Aromatic Ring Construction

By: Ken Tanaka (author)Hardback

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Description

Recent significant advances with transition-metal-mediated reactions have opened promising new routes to complex aromatic compounds and have been the subject of intense research in recent years. Featuring practical and efficient reactions to help organic chemists synthesize an important class of compounds, Transition-Metal-Mediated Aromatic Ring Construction provides a valuable guide to methods, synthetic routes, and strategies to construct aromatic rings. Chapters devoted to efficient and practical reactions demonstrate how to use them for the synthesis of various complex aromatic compounds.

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About Author

KEN TANAKA is Professor in the Department of Applied Chemistry at the Tokyo University of Agriculture and Technology. Previously, he worked for the Mitsubishi Chemical Corporation in organic process research. Dr. Tanaka has published more than 100 scientific papers concerning transition-metal catalysis.

Contents

CONTRIBUTORS xvii PREFACE xxi PART I [2 + 2 + 2] AND RELATED CYCLOADDITION REACTIONS 1 Cobalt-Mediated [2+2+2] Cycloaddition 3 Vincent Gandon 1.1 Introduction, 3 1.2 Synthesis of Benzenes, 4 1.3 Synthesis of Heterocycles, 15 1.4 Mechanistic Aspects, 24 1.5 Synthetic Applications, 26 1.6 Summary and Outlook, 30 References, 31 2 Nickel-Mediated [2+2+2] Cycloaddition 37 Puneet Kumar and Janis Louie 2.1 Introduction, 37 2.2 Synthesis of Benzenes, 37 2.3 Cycloaddition of Alkynes and Nitriles, 45 2.4 Cycloaddition of Alkynes and Imines, 49 2.5 Cycloaddition of Alkynes and Carbon Dioxide, 50 2.6 Cycloaddition of Alkynes and Isocyanates, 51 2.7 Cycloaddition of Alkynes and Carbodiimide, 54 2.8 Cycloaddition of Diynes and Ketenes, 54 2.9 Cycloaddition of Arynes, 55 2.10 Mechanism, 58 2.11 Summary and Outlook, 69 References, 69 3 Ruthenium-Mediated [2+2+2] Cycloaddition 71 Yoshihiko Yamamoto 3.1 Introduction, 71 3.2 Synthesis of Benzenes, 72 3.3 Synthesis of Heterocycles, 92 3.4 Mechanism of Ruthenium-Catalyzed [2+2+2] Cycloadditions, 101 3.5 Synthetic Applications, 111 3.6 Summary and Outlook, 119 References, 120 4 Rhodium-Mediated [2+2+2] Cycloaddition 127 Ken Tanaka 4.1 Introduction, 127 4.2 Synthesis of Benzenes, 128 4.3 Synthesis of Pyridines, 147 4.4 Synthesis of Pyridones and Related Heterocycles, 153 4.5 Summary and Outlook, 157 References, 158 5 Iridium-Mediated [2+2+2] Cycloaddition 161 Ryo Takeuchi 5.1 Introduction, 161 5.2 Synthesis of Benzene Derivatives, 162 5.3 Synthesis of Heterocyclic Compounds, 169 5.4 Mechanistic Aspects, 175 5.5 Summary and Outlook, 179 References, 179 6 [2+2+2] and Related Cycloadditions Mediated by Other Transition Metals 183 Ken Tanaka and Yu Shibata 6.1 Introduction, 183 6.2 Palladium-Catalyzed [2+2+2] and [2+2+1] Cycloadditions, 183 6.3 Iron-Catalyzed [2+2+2] Cycloaddition, 196 6.4 Manganese-Catalyzed [2+2+2] Cycloaddition, 199 6.5 Rhenium-Catalyzed [2+2+2], [2+1+2+1], and [2+2+1+1] Cycloadditions, 200 6.6 Other Transition-Metal-Catalyzed [2+2+2] Cycloaddition, 202 6.7 Summary and Outlook, 203 References, 203 7 Application to the Synthesis of Natural Products 207 Bernhard Witulski and Julien Grand 7.1 Introduction, 207 7.2 Construction of Benzene Rings, 209 7.3 Construction of a Heterocyclic Ring, 226 7.4 Miscellaneous, 231 7.5 Summary and Outlook, 238 References, 239 8 Synthesis of Planar Chiral Aromatic Compounds via [2+2+2] Cycloaddition 243 Takanori Shibata and Ken Tanaka 8.1 Introduction, 243 8.2 Cobalt-Catalyzed [2+2+2] Cycloaddition, 246 8.3 Rhodium-Catalyzed [2+2+2] Cycloaddition, 247 8.4 Enantioselective [2+2+2] Cycloaddition, 249 8.5 Summary and Outlook, 252 References, 252 9 Synthesis of Axially Chiral Aromatic Compounds via [2+2+2] Cycloaddition 255 Ken Tanaka and Takanori Shibata 9.1 Introduction, 255 9.2 Cobalt-Catalyzed Enantioselective [2+2+2] Cycloaddition, 256 9.3 Iridium-Catalyzed Enantioselective [2+2+2] Cycloaddition, 258 9.4 Rhodium-Catalyzed Enantioselective [2+2+2] Cycloaddition, 263 9.5 Enantioselective Synthesis of Axially Chiral Anilides and Bezamides, 275 9.6 Summary and Outlook, 278 References, 278 10 Synthesis of Helically Chiral Aromatic Compounds via [2+2+2] Cycloaddition 281 Ken Tanaka 10.1 Introduction, 281 10.2 Nonasymmetric Synthesis, 281 10.3 Diastereoselective Synthesis, 287 10.4 Enantioselective Synthesis, 290 10.5 Summary and Outlook, 296 References, 297 11 Aromatic Ring Construction from Zirconocenes and Titanocenes 299 Shi Li and Tamotsu Takahashi 11.1 Introduction, 299 11.2 Aromatic Ring Construction from Zirconocenes, 300 11.3 Aromatic Ring Construction from Titanocenes, 313 11.4 Application to Synthesis of Substituted Acenes, 315 11.5 Summary and Outlook, 317 References, 318 PART II [4+2], [3+2], AND RELATED CYCLOADDITION REACTIONS 12 [4+2] and [3+2] Cycloaddition via Metallacycles 323 Takuya Kurahashi and Seijiro Matsubara 12.1 Introduction, 323 12.2 [4+2] Cycloaddition via Elimination of Small Molecules, 326 12.3 [3+2] Cycloaddition via Elimination of Small Molecules, 332 12.4 [4+2] Cycloaddition via C C Bond Activation, 334 12.5 [4+2] Cycloaddition via C H Bond Activation, 336 12.6 Summary and Outlook, 339 References, 339 13 Diels Alder Reactions 341 Gerhard Hilt and Florian Punner 13.1 Introduction, 341 13.2 Transition-Metal-Mediated Diels Alder Reaction/Aromatization Sequence, 342 13.3 Intramolecular Diels Alder Reactions toward Dihydroaromatic and Aromatic Products, 349 13.4 Synthetic Applications, 350 13.5 Summary and Outlook, 352 References, 352 14 [4+2] Benzannulation of Enynes with Alkynes 355 Vladimir Gevorgyan and Olga V. Zatolochnaya 14.1 Introduction, 355 14.2 Benzannulation of Enyne with Alkyne: Gold-catalyzed Benzannulation Reaction, 356 14.3 Benzannulation of Enyne with Enyne, 358 14.4 Benzannulation of Enyne with Diyne, 365 14.5 Synthetic Applications, 371 14.6 Summary and Outlook, 376 References, 376 15 Formal [4+2] Benzannulation via Pyrylium Intermediates 379 Naoki Asao and Yoshifumi Ishikawa 15.1 Introduction, 379 15.2 Benzannulation of Pyrylium Salts, 380 15.3 Benzannulation of O-Alkynylbenzaldehydes, 380 15.4 Intramolecular [4+2] Benzannulation, 392 15.5 Application to Natural Product Synthesis, 394 15.6 Summary and Outlook, 395 References, 396 16 Utilization of 1,3-Dipolar Compounds 399 Yi-Feng Wang and Shunsuke Chiba 16.1 Introduction, 399 16.2 1,3-Dipolar Cycloaddition, 401 16.3 Five-Membered Ring Construction via Decomposition of Azides, 410 16.4 Six-Membered Ring Construction via Decomposition of Azides, 418 16.5 Summary and Outlook, 421 References, 422 17 Utilization of Transition-Metal Carbenoids 425 James Wallace Herndon, Jr. 17.1 Introduction, 425 17.2 Five-membered Aromatic Ring Construction, 426 17.3 Six-Membered Aromatic Ring Construction, 432 17.3.1 Dotz Benzannulation Reaction, 432 17.4 Summary and Outlook, 450 References, 450 PART III ELECTROCYCLIZATION REACTIONS 18 Intramolecular Hydroarylation of Alkynes, Alkenes, and Allenes 457 Tsugio Kitamura 18.1 Introduction, 457 18.2 Intramolecular Hydroarylation, 457 18.3 Summary and Outlook, 482 References, 483 19 Intramolecular C X Bond Formation between C X or X H andAlkynes 485 Hiroaki Ohno 19.1 Introduction, 485 19.2 C X Bond Formation between C X and Alkynes, 485 19.3 C X Bond Formation between X H and Alkynes, 510 19.4 Summary and Outlook, 529 References, 529 20 Synthesis of Heterocycles via X H Bond Addition to Diynes 537 Takanori Matsuda 20.1 Introduction, 537 20.2 Synthesis of Pyrroles and Furans via Double trans Addition to 1,3-Diynes, 538 20.3 Synthesis of Pyrroles via Hydroamination of 1,4- and 1,5-Diynes, 542 20.4 Synthesis of Siloles and Germoles via Double trans Addition to 1,3-Diynes, 543 20.5 Summary and Outlook, 546 References, 546 21 Cycloaromatization via Transition Metal Cumulenylidenes 549 Yoshiaki Nishibayashi 21.1 Introduction, 549 21.2 Cycloaromatization via Chromium , Molybdenum , and Tungsten Vinylidene Complexes, 550 21.3 Cycloaromatization via Ruthenium Vinylidene Complexes, 554 21.4 Cycloaromatization via Rhodium Vinylidene Complexes, 558 21.5 Cycloaromatization via Gold Vinylidene Complexes, 561 21.6 Cycloaromatization via Ruthenium Allenylidene Complexes, 565 21.7 Summary and Outlook, 565 References, 566 PART IV COUPLING AND ADDITION REACTIONS 22 C C Bond-Forming Coupling Reactions 573 Masaki Shimizu 22.1 Introduction, 573 22.2 Cyclization, 574 22.3 Annulation, 597 22.4 Summary and Outlook, 612 References, 612 23 Synthesis of Carbazoles and Related Compounds via C E Bond-Forming Coupling Reactions 617 Koji Nakano 23.1 Introduction, 617 23.2 Synthesis of Carbazoles, 618 23.3 Synthesis of Dibenzofurans and Dibenzothiophenes, 633 23.4 Synthesis of Other Dibenzoheteroles, 637 23.5 Summary and Outlook, 642 References, 642 24 Synthesis of Aromatic Benzo-Fused Five- and Six-Membered Heterocycles via Palladium- and Copper-Catalyzed C X Bond-Forming Reactions 645 Catherine J. Ball and Michael C. Willis 24.1 Introduction, 645 24.2 C N Bond Formation, 646 24.3 C O Bond Formation, 662 24.4 C S Bond Formation, 667 24.5 Annulation of Anilines and Related Compounds with Alkynes, 671 24.6 Summary and Outlook, 676 References, 677 25 Coupling Reactions of the sp2 C H Bond with Alkynes 683 Tetsuya Satoh and Masahiro Miura 25.1 Introduction, 683 25.2 Synthesis of Arenes, 685 25.3 Synthesis of Heterocycles, 697 25.4 Summary and Outlook, 716 References, 716 PART V OTHER IMPORTANT TRANSFORMATIONS 26 Metathesis Reactions 721 Kazuhiro Yoshida 26.1 Introduction, 721 26.2 Alkene Metathesis, 722 26.3 Ene Yne Metathesis, 736 26.4 Other Applications, 738 26.5 Summary and Outlook, 740 References and Notes, 741 27 Skeletal Rearrangement Reactions 743 Itaru Nakamura 27.1 Introduction, 743 27.2 -Electrophilic Transition-Metal-Mediated Aromatization Reactions, 743 27.3 -Electrophilic Transition-Metal-Mediated Aromatization Reactions, 768 27.4 Summary and Outlook, 769 References, 769 28 Dearomatization Aromatization Sequence 773 Hiroto Yoshida 28.1 Introduction, 773 28.2 Reactions via Arynes, 774 28.3 Reactions via o-Quinodimethanes, 787 28.4 Summary and Outlook, 793 References, 794 INDEX 797

Product Details

  • publication date: 04/10/2013
  • ISBN13: 9781118148921
  • Format: Hardback
  • Number Of Pages: 830
  • ID: 9781118148921
  • weight: 1310
  • ISBN10: 1118148924

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