Elektrooxidative Synthese von Bis- und Oligoarenen

• Antragsteller: Professor Dr. Siegfried R. Waldvogel
• Fachliche Zuordnung: Organische Molekülchemie - Synthese, Charakterisierung
• Förderung: Förderung von 2015 bis 2019
• Projektkennung: Deutsche Forschungsgemeinschaft (DFG) - Projektnummer 286171883

• Erstellungsjahr: 2019

Zusammenfassung der Projektergebnisse

Within the project we made a significant process in expanding the scope of the electrooxadative synthesis of bis- and oligoarenes. We were pleased to see that phenols show such a high electrochemically robustness allowing to apply high current densities in the cross-coupling reaction of 2,2’-biphenols. Furthermore, the initial hints that the selectivity of the cross-coupling reactions might strongly rely on the oxidation potentials and solvate structures of the used substrates was underlined by our findings. The key to trigger a certain reactivity and selectivity in the cross-coupling reactions is the use of HFIP as solvent in combination with additives like methanol or water. Additionally, we could successfully provide a simple and efficient electrochemical protocol for the single and two-folded synthesis of linear bi- and terphenyl structures. These structure motives provide suitable building blocks for the further functionalization to potential quateraryl-based α-helix mimetics by means of modern transition-metal catalyzed synthesis.

Projektbezogene Publikationen (Auswahl)

• Selective Synthesis of Partially Protected Non-Symmetric Biphenols by Reagent- and Metal-Free Anodic Cross-Coupling Reaction, Angew. Chem. Int. Ed. 2016, 55, 11801–11805
  A. Wiebe, D. Schollmeyer, K. M. Dyballa, R. Franke, S. R. Waldvogel
  
• Synthesis of meta-Terphenyl-2,2''-diols by Anodic C,C Cross-Coupling Reaction, Angew. Chem. Int. Ed. 2016, 55, 10872–10876
  S. Lips, A. Wiebe, B. Elsler, D. Schollmeyer, K. M. Dyballa, R. Franke, S. R. Waldvogel
  
• Electro-organic Synthesis as Sustainable Alternative for Dehydrogenative Cross-Coupling of Phenols and Naphthols, Synthesis 2017, 49, 252– 259
  B. Riehl, K. Dyballa, R. Franke, S. R. Waldvogel
  
• Reagent- and Metal-free Anodic C,C Cross-Coupling of Aniline Derivatives, Angew. Chem. Int. Ed. 2017, 56, 4877–4881
  L. Schulz, M. Enders, B. Elsler, D. Schollmeyer, K. M. Dyballa, R. Franke, S. R. Waldvogel
  
• Single and Twofold Metal- and Reagent-Free Anodic C,C Cross-Coupling of Phenols with Thiophenes, Angew. Chem. Int. Ed. 2017, 56, 14727–14731
  A. Wiebe, S. Lips, D. Schollmeyer, R. Franke, S. R. Waldvogel
  
• The Catalytic Effect of Fluoroalcohol Mixtures Depends on Domain Formation, ACS Catal. 2017, 7, 1846–1852
  O. Holloczki, A. Berkessel, J. Mars, M. Mezger, A. Wiebe, S. R. Waldvogel, B. Kirchner
  
• Unexpected high robustness of electrochemical cross-coupling for a broad range of current density, Sci. Adv. 2017, 3, eaao3920/1–7
  A. Wiebe, B. Riehl, S. Lips, R. Franke, S. R. Waldvogel
  
• Electrochemical, Synthesis of 2-Hydroxy-para-terphenyls by Dehydrogenative Anodic C,C Cross-Coupling Reaction, Synlett 2019, 30, 1174–1177
  S. Lips, R. Franke, S. Waldvogel
  
• Selective Formation of 4,4’-Biphenols by Anodic Dehydrogenative Cross- and Homo-Coupling Reaction, Chem. Eur. J. 2019, 25, 2713–2716
  B. Dahms, P. J. Kohlpaintner, A. Wiebe, R. Breinbauer, D. Schollmeyer, S. R. Waldvogel