Skip to main content
SpringerLink
Log in
Book cover

Grundlagen der metallorganischen Komplexkatalyse pp 258–282Cite as

Hydrocyanierungen, -silylierungen und -aminierungen von Olefinen

  • Chapter

  • 4889 Accesses

Zusammenfassung

Die Addition von Verbindungen mit einer Element–Wasserstoff-Bindung H–X wie H–CN, H–SiR3 oder H–NR2 (R = Alkyl, Aryl, H) an Olefine führt zu funktionalisierten Alkanen.

This is a preview of subscription content, log in via an institution.

Chapter
USD   29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD   39.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever

Tax calculation will be finalised at checkout

Purchases are for personal use only

Learn about institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Kapitel 11

Wichtige Monographien: [M2], [M12]

  • F. Alonso, I. P. Beletskaya, M. Yus, Tetrahedron 2008, 64, 3047: „Non-Conventional Methodologies for Transition-Metal Catalysed Carbon–Carbon Coupling: A Critical Overview. Part 2: The Suzuki Reaction“

    Article  CAS  Google Scholar 

  • R. Álvarez, O. N. Faza, A. R. de Lera, D. J. Cárdenas, Adv. Synth. Catal. 2007, 349, 887: „A Density Functional Theory Study of the Stille Cross-Coupling via Associative Transmetalation. The Role of Ligands and Coordinating Solvents“

    Article  Google Scholar 

  • C. Amatore, A. Jutand, Acc. Chem. Res. 2000, 33, 314: „Anionic Pd(0) and Pd(II) Intermediates in Palladium-Catalyzed Heck and Cross-Coupling Reactions“

    Article  CAS  Google Scholar 

  • I. P. Beletskaya, A. V. Cheprakov, Chem. Rev. 2000, 100, 3009: „The Heck Reaction as a Sharpening Stone of Palladium Catalysis“

    Article  CAS  Google Scholar 

  • I. P. Beletskaya, A. V. Cheprakov, J. Organomet. Chem. 2004, 689, 4055: „Palladacycles in Catalysis – a Critical Survey“

    Article  CAS  Google Scholar 

  • I. P. Beletskaya, A. V. Cheprakov, Coord. Chem. Rev. 2004, 248, 2337: „Copper in Cross-Coupling Reactions. The Post-Ullmann Chemistry“

    Article  CAS  Google Scholar 

  • F. Bellina, A. Carpita, R.. Rossi, Synthesis, 2004, 2419: „Palladium Catalysts for the Suzuki Cross- Coupling Reaction: An Overview of Recent Advances“

    Google Scholar 

  • C. Bolm, J. Legros, J. Le Paih, L. Zani, Chem. Rev. 2004, 104, 6217: „Iron-Catalyzed Reactions in Organic Synthesis“

    Article  CAS  Google Scholar 

  • M. Braun, T. Meier, Angew. Chem. 2006, 118, 7106: „Tsuji-Trost-Allylierung mit Ketonenolaten“

    Article  Google Scholar 

  • A. Brennführer, H. Neumann, M. Beller, Angew. Chem. 2009, 121, 4176: „Palladiumkatalysierte Carbonylierungen von Arylhalogeniden und ähnlichen Substraten“

    Article  Google Scholar 

  • S. L. Buchwald (ed.), Acc. Chem. Res. 2008, 41 (11), 1439: Special Issue on Cross Coupling

    Google Scholar 

  • W. Cabri, I. Candiani, Acc. Chem. Res. 1995, 28, 2: „Recent Developments and New Perspectives in the Heck Reaction“

    Article  CAS  Google Scholar 

  • D. J. Cárdenas, Angew. Chem. 1999, 111, 3201: „Auf dem Weg zu wirksamen und vielseitigen Metallkatalysierten Alkyl-Alkyl-Kreuzkupplungen“

    Article  Google Scholar 

  • D. J. Cárdenas, Angew. Chem. 2003, 115, 398: „Metall-katalysierte Alkyl-Alkyl-Kreuzkupplungen in Gegenwart funktioneller Gruppen“

    Article  Google Scholar 

  • D. J. Cárdenas, A. M. Echavarren, New J. Chem. 2004, 28, 338: „Mechanistic Aspects of C–C Bond Formation Involving Allylpalladium Complexes: The Role of Computational Studies“

    Article  Google Scholar 

  • R. Chinchilla, C. Nájera, Chem. Rev. 2007, 107, 874: „The Sonogashira Reaction: A Booming Methodology in Synthetic Organic Chemistry“

    Article  CAS  Google Scholar 

  • U. Christmann, R. Vilar, Angew. Chem. 2005, 117, 370: „Einfach koordinierte Palladiumspezies als Katalysatoren in Kreuzkupplungen“

    Article  Google Scholar 

  • G. Consiglio, R. M. Waymouth, Chem. Rev. 1989, 89, 257: „Enantioselective Homogeneous Catalysis Involving Transition-Metal−Allyl Intermediates“

    Article  CAS  Google Scholar 

  • G. T. Crisp, Chem. Soc. Rev. 1998, 27, 427: „Variations on a Theme – Recent Developments on the Mechanism of the Heck Reaction and their Implications for Synthesis“

    Article  CAS  Google Scholar 

  • A. Dedieu, Chem. Rev. 2000, 100, 543: „Theoretical Studies in Palladium and Platinum Molecular Chemistry“

    Article  CAS  Google Scholar 

  • S. E. Denmark, C. S. Regens, Acc. Chem. Res. 2008, 41, 1486: „Palladium-Catalyzed Cross-Coupling Reactions of Organosilanols and Their Salts: Practical Alternatives to Boron- and Tin-Based Methods“

    Article  CAS  Google Scholar 

  • H. Doucet, J.-C. Hierso, Angew. Chem. 2007, 119, 850: „Palladium-Katalysatorsysteme für die Synthese von konjugierten Eninen durch Sonogashira-Kupplungen und verwandte Alkinylierungen“

    Article  Google Scholar 

  • H. Doucet, Eur. J. Org. Chem. 2008, 2013: „Suzuki–Miyaura Cross-Coupling Reactions of Alkylboronic Acid Derivatives or Alkyltrifluoroborates with Aryl, Alkenyl or Alkyl Halides and Triflates“

    Google Scholar 

  • J. Dupont, C. S. Consorti, J. Spencer, Chem. Rev. 2005, 105, 2527: „The Potential of Palladcycles: More Than Just Precatalysts“

    Article  CAS  Google Scholar 

  • P. Espinet, A. M. Echavarren, Angew. Chem. 2004, 116, 4808: „Die Mechanismen der Stille-Reaktion“

    Google Scholar 

  • V. Farina, Adv. Synth. Catal. 2004, 346, 1553: „High-Turnover Palladium Catalysts in Cross-Coupling and Heck Chemistry: A Critical Overview“

    Article  CAS  Google Scholar 

  • A. C. Frisch, M. Beller, Angew. Chem. 2005, 117, 680: „Katalysatoren machen's möglich: Selektive C-C-Kupplungen mit nichtaktivierten Alkylhalogeniden“

    Article  Google Scholar 

  • G. C. Fu, Acc. Chem. Res. 2008, 41, 1555: „The Development of Versatile Methods for Palladium-Catalyzed Coupling Reactions of Aryl Electrophiles through the Use of P(t-Bu)3 and PCy3 as Ligands“

    Article  CAS  Google Scholar 

  • A. Fürstner, Angew. Chem. 2009, 121, 1390: „Aus dem Schatten ins Rampenlicht: Eisen(-Domino)- Katalyse“

    Article  Google Scholar 

  • F. Glorius, Angew. Chem. 2008, 120, 8474: „Asymmetrische Kreuzkupplung von nicht-aktivierten sekundären Alkylhalogeniden“

    Article  Google Scholar 

  • A. E. Jensen, P. Knochel, J. Org. Chem. 2002, 67, 79: „Nickel-Catalyzed Cross-Coupling between Functionalized Primary or Secondary Alkylzinc Halides and Primary Alkyl Halides“

    Article  CAS  Google Scholar 

  • J. B. Johnson, T. Rovis, Angew. Chem. 2008, 120, 852: „Nicht ganz unbeteiligt: der Einfluss von Olefinen auf übergangsmetallkatalysierte Kreuzkupplungen“

    Article  Google Scholar 

  • E. A. B. Kantchev, C. J. O'Brien, M. G. Organ, Angew. Chem. 2007, 119, 2824: „Aus der Sicht des Synthetikers: Palladiumkomplexe N-heterocyclischer Carbene als Katalysatoren für Kreuzkupplungen“

    Article  Google Scholar 

  • A. O. King, N. Yasuda, Top. Organomet. Chem. 2004, 6, 205: „Palladium-Catalyzed Cross-Coupling Reactions in the Synthesis of Pharmaceuticals“

    CAS  Google Scholar 

  • J. Kleimark, A. Hedström, P.-F. Larsson, C. Johansson, P.-O. Norrby, ChemCatChem 2009, 1, 152: „Mechanistic Investigation of Iron-Catalyzed Coupling Reactions“

    Article  CAS  Google Scholar 

  • S. Kotha, K. Lahiri, D. Kashinath, Tetrahedron 2002, 58, 9633: „Recent Applications of the Suzuki– Miyaura Cross-Coupling Reaction in Organic Synthesis“

    Article  CAS  Google Scholar 

  • S. Kozuch, S. Shaik, A. Jutand, C. Amatore, Chem. Eur. J. 2004, 10, 3072: „Active Anionic Zero-Valent Palladium Catalysts: Characterization by Density Functional Calculations“

    Article  CAS  Google Scholar 

  • S. Kozuch, C. Amatore, A. Jutand, S. Shaik, Organometallics 2005, 24, 2319: „What Makes for a Good Catalytic Cycle? A Theoretical Study of the Role of an Anionic Palladium(0) Complex in the Cross- Coupling of an Aryl Halide with an Anionic Nucleophile“

    Article  CAS  Google Scholar 

  • B.-L. Lin, L. Liu, Y. Fu, S.-W. Luo, Q. Chen., Q.-X. Guo, Organometallics, 2004, 23, 2114: „Comparing Nickel- and Palladium-Catalyzed Heck Reactions“

    Article  CAS  Google Scholar 

  • A. F. Littke, G. C. Fu, Angew. Chem. 2002, 114, 4350: „Palladiumkatalysierte Kupplungen von Arylchloriden“

    Article  Google Scholar 

  • Z. Lu, S. Ma, Angew. Chem. 2008, 120, 264: „Metallkatalysierte enantioselektive Allylierungen in der asymmetrischen Synthese“

    Article  Google Scholar 

  • E.-i. Negishi (ed.), Handbook of Organopalladium Chemistry for Organic Synthesis, Vol. 1–2, Wiley- Interscience, New York 2002

    Google Scholar 

  • E.-i. Negishi, Dalton Trans. 2005, 827: “A Quarter of a Century of Explorations in Organozirconium Chemistry“

    Google Scholar 

  • M. R. Netherton, G. C. Fu, Adv. Synth. Catal. 2004, 346, 1525: „Nickel-Catalyzed Cross-Couplings of Unactivated Alkyl Halides and Pseudohalides with Organometallic Compounds“ (und dort zit. Literatur)

    Article  CAS  Google Scholar 

  • A. Rudolph, M. Lautens, Angew. Chem. 2009, 121, 2694: „Sekundäre Alkylhalogenide in übergangsmetallkatalysierten Kreuzkupplungen“

    Article  Google Scholar 

  • H. v. Schenck, B. Åkermark, M. Svensson, J. Am. Chem. Soc. 2003, 125, 3503: „Electronic Control of the Regiochemistry in the Heck Reaction“

    Article  Google Scholar 

  • B. D. Sherry, A. Fürstner, Acc. Chem. Res. 2008, 41, 1500: „The Promise and Challenge of Iron- Catalyzed Cross Coupling“

    Article  CAS  Google Scholar 

  • H. Shinokubo, K. Oshima, Eur. J. Org. Chem. 2004, 2081: „Transition Metal-Catalyzed Carbon–Carbon Bond Formation with Grignard Reagents – Novel Reactions with a Classic Reagent“

    Google Scholar 

  • J. P. Stambuli, C. D. Incarvito, M. Bühl, J. F. Hartwig, J. Am. Chem. Soc. 2004, 126, 1184: „Synthesis, Structure, Theoretical Studies, and Ligand Exchange Reactions of Monomeric, T-Shaped Arylpalladium( II) Halide Complexes with an Additional, Weak Agostic Interaction“

    Article  CAS  Google Scholar 

  • J. K. Stille, Angew. Chem. 1986, 98, 504: „Palladium-katalysierte Kupplungsreaktionen organischer Elektrophile mit Organozinn-Verbindungen“

    Article  CAS  Google Scholar 

  • A. Suzuki, Chem. Commun. 2005, 4759: „Carbon–Carbon Bonding Made Easy“

    Google Scholar 

  • K. Tamao, T. Hiyama, E.-i. Negishi (eds.), J. Organomet. Chem. 2002, 653, 1: „Special Issue: 30 Years of the Cross-Coupling Reaction“ und insbesondere die „Historical Notes“ von K. Tamao (S. 23), S.-I. Murahashi (S. 27), E.-i. Negishi (S. 34), K. Sonogashira (S. 46), N. Miyaura (S. 54) und T. Hiyama (S. 58)

    Google Scholar 

  • L. F. Tietze, H. Ila, H. P. Bell, Chem. Rev. 2004, 104, 3453: „Enantioselective Palladium-Catalyzed Transformations“

    Article  CAS  Google Scholar 

  • B. M. Trost, Acc. Chem. Res. 1996, 29, 355: „Designing a Receptor for Molecular Recognition in a Catalytic Synthetic Reaction: Allylic Alkylation“

    Article  CAS  Google Scholar 

  • A. M. Trzeciak, J. J. Ziólkowski, Coord. Chem, Rev. 2007, 251, 1281: „Monomolecular, Nanosized and Heterogenized Palladium Catalysts for the Heck Reaction“

    Article  CAS  Google Scholar 

  • R. R. Tykwinski, Angew. Chem. 2003, 115, 1604: „Palladium-katalysierte Kreuzkupplungen zwischen sp- und sp2-hybridisierten Kohlenstoffatomen“

    Article  Google Scholar 

  • J. G. de Vries, Dalton Trans. 2006, 421: „A Unifying Mechanism for All High-Temperature Heck Reactions. The Role of Palladium Colloids and Anionic Species“

    Google Scholar 

  • A. Zapf, M. Beller, Top. Catal. 2002, 19, 101, siehe Kap. 10.

    Google Scholar 

Download references

Authors
  1. Prof.Dr. Dirk Steinborn
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

Copyright information

© 2010 Vieweg+Teubner | GWV Fachverlage GmbH

About this chapter

Cite this chapter

Steinborn, D. (2010). Hydrocyanierungen, -silylierungen und -aminierungen von Olefinen. In: Grundlagen der metallorganischen Komplexkatalyse. Vieweg+Teubner. https://doi.org/10.1007/978-3-8348-9375-8_12

Download citation

Publish with us

Policies and ethics

Search

Navigation