Synthese und Reaktivität von benzylischen und allylischen Zinkverbindungen

• Applicant: Professor Dr. Paul Knochel
• Subject Area: Organic Molecular Chemistry - Synthesis and Characterisation
• Term: from 2002 to 2011
• Project identifier: Deutsche Forschungsgemeinschaft (DFG) - Project number 5394413

• Final Report Year: 2011

Final Report Abstract

Im Rahmen dieses DFG-Projektes haben wir eine Reihe neuer benzylischer und allylischer Zinkorganylen erzeugt und ihre Nützlichkeit in der Synthese zeigen können. Wir haben eine neue effiziente Ibuprofensynthese entwickelt und patentiert.

Publications

• “A General Preparation of Polyfunctional Benzylic Zinc Organometallic Compounds”. Chem. Asian J. 2008, 3, 1678-1691
  Metzger, A.; Schade, M. A.; Manolikakes, G.; Knochel, P.
  
• “Highly Diastereoselective Addition of Cinnamylzinc Derivatives to α-Chiral Carbonyl Compounds”. Org. Lett. 2008, 10, 117-120
  Dunet, G.; Mayer, P.; Knochel, P.
  
• “LiCl-Mediated Preparation of Highly Functionalized Benzylic Zinc Chlorides”. Org. Lett. 2008, 10, 1107-1110
  Metzger, A.; Schade, M. A.; Knochel, P.
  
• “Nickel-catalyzed cross-coupling reactions of benzylic zinc reagents with aromatic bromides, chlorides and tosylates”. Chem. Comm. 2008, 3046-3048
  Schade, M. A.; Metzger, A.; Hug, S.; Knochel, P.
  
• “Palladium- and Nickel-Catalyzed Cross-Couplings of Unsaturated Halides Bearing Relatively Acidic Protons with Organozinc Reagents”. J. Org. Chem. 2008, 73, 8422-8436
  Manolikakes, G.; Munoz Hernandez, C.; Schade, M. A.; Metzger, A.; Knochel, P.
  
• “Polyfunctional benzylic zinc chlorides by the direct insertion of magnesium into benzylic chlorides in the presence of LiCl and ZnCl2”. Chem. Comm. 2008, 5824-5826
  Metzger, A.; Piller, F. M.; Knochel, P.
  
• Transition-Metal Catalyzed Cross-Coupling Reactions of Functionalized Organometallic Reagents, Nickel-Catalyzed Amination of Aryl Chlorides and Preparation and Reactions of Organozinc Reagents. Dissertation, 2009
  Georg Manolikakes
  
• „Preparation of Polyfunctional Arylmagnesium, Arylzinc, and Benzylic Zinc Reagents by Using Magnesium in the Presence of LiCl”. Chem. Eur. J. 2009, 15, 7192-7202
  Piller, F. M.; Metzger, A.; Schade, M. A.; Haag, B. A.; Gavryushin, A.; Knochel, P.
  
• LiCl-Mediated Direct Insertion of Magnesium Into Aryl, Heteroaryl and Benzylic Halides. Dissertation, 2010
  Fabian Piller
  
• Preparation and Application of Benzylic Zinc Chlorides. Lewis-Acid Promoted Additions of Organomagnesium and Organozinc Reagents to Carbonyl Derivatives. Transition Metal-Catalyzed Cross-Coupling Reactions with Methylthio-Substitutes N-Heterocycles. Dissertation, 2010
  Albrecht Metzger
  
• “Direct addition of functionalized organozinc reagents to carbon dioxide, ketones, and aldehydes in the presence of MgCl2”. Synthesis 2010, 3802-3810
  Bernhardt, S.; Metzger, A.; Knochel, P.
  
• “Large-scale preparation of polyfunctional benzylic zinc reagents by direct insertion of zinc dust into benzylic chlorides in the presence of lithium chloride”. Synthesis 2010, 882-891
  Metzger, A.; Argyo, C.; Knochel, P.
  
• “MgCl2-Accelerated Addition of Functionalized Organozinc Reagents to Aldehydes, Ketones, and Carbon Dioxide”. Angew. Chem. Int. Ed. 2010, 49, 4665-4668
  Metzger, A.; Bernhardt, S.; Manolikakes, G.; Knochel, P.
  
• Cross-Coupling of Benzylic Zinc Reagents, Preparation and Applications of Alkenyl Zinc Reagents, Preparation of Primary Amides and Synthesis of Functionalized Allenes. Dissertation, 2011
  Matthias Schade
  
• Preparation of Di- and Tri-Functionalized Aromatics and Heterocycles Transition Metal-Catalyzed Cross-Coupling Reactions of Thioethers. Chlorine-Zinc Exchange Reactions. Dissertation, 2011
  Laurin Melzig
  
• Synthesis, Functionalization, and Polymerization of Heterocycles Using Frustrated Lewis Pairs, Boron, Magnesium, and Zinc Organometallics. Dissertation, 2011
  Benjamin Haag
  
• „Pd- and Ni-Catalyzed Cross-Coupling Reactions of Functionalized Organozinc Reagents with Unsaturated Thioethers”. Chem. Eur. J. 2011, 17, 2948-2956
  Melzig, L.; Metzger, A.; Knochel, P.