Electrooxidative Synthesis of Bis- and Oligoarenes

• Applicant: Professor Dr. Siegfried R. Waldvogel
• Subject Area: Organic Molecular Chemistry - Synthesis and Characterisation
• Term: from 2015 to 2019
• Project identifier: Deutsche Forschungsgemeinschaft (DFG) - Project number 286171883

• Final Report Year: 2019

Final Report Abstract

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.

Publications

• Electro-organic Synthesis as Sustainable Alternative for Dehydrogenative Cross-Coupling of Phenols and Naphthols, Synthesis 2017, 49, 252– 259
  Waldvogel, Siegfried; Riehl, Barbara; Dyballa, Katrin & Franke, Robert
  
• 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
  Wiebe, Anton; Schollmeyer, Dieter; Dyballa, Katrin M.; Franke, Robert & Waldvogel, Siegfried R.
  
• Synthesis of meta-Terphenyl-2,2''-diols by Anodic C,C Cross-Coupling Reaction, Angew. Chem. Int. Ed. 2016, 55, 10872–10876
  Lips, Sebastian; Wiebe, Anton; Elsler, Bernd; Schollmeyer, Dieter; Dyballa, Katrin M.; Franke, Robert & Waldvogel, Siegfried R.
  
• Reagent- and Metal-free Anodic C,C Cross-Coupling of Aniline Derivatives, Angew. Chem. Int. Ed. 2017, 56, 4877–4881
  Schulz, Lara; Enders, Mathias; Elsler, Bernd; Schollmeyer, Dieter; Dyballa, Katrin M.; Franke, Robert & Waldvogel, Siegfried R.
  
• Single and Twofold Metal- and Reagent-Free Anodic C,C Cross-Coupling of Phenols with Thiophenes, Angew. Chem. Int. Ed. 2017, 56, 14727–14731
  Wiebe, Anton; Lips, Sebastian; Schollmeyer, Dieter; Franke, Robert & Waldvogel, Siegfried R.
  
• The Catalytic Effect of Fluoroalcohol Mixtures Depends on Domain Formation, ACS Catal. 2017, 7, 1846–1852
  Hollóczki, Oldamur; Berkessel, Albrecht; Mars, Julian; Mezger, Markus; Wiebe, Anton; Waldvogel, Siegfried R. & Kirchner, Barbara
  
• Unexpected high robustness of electrochemical cross-coupling for a broad range of current density, Sci. Adv. 2017, 3, eaao3920/1–7
  Wiebe, Anton; Riehl, Barbara; Lips, Sebastian; Franke, Robert & Waldvogel, Siegfried R.
  
• Electrochemical, Synthesis of 2-Hydroxy-para-terphenyls by Dehydrogenative Anodic C,C Cross-Coupling Reaction, Synlett 2019, 30, 1174–1177
  Lips, Sebastian; Franke, Robert & Waldvogel, Siegfried R.
  
• Selective Formation of 4,4’-Biphenols by Anodic Dehydrogenative Cross- and Homo-Coupling Reaction, Chem. Eur. J. 2019, 25, 2713–2716
  Dahms, Benedikt; Kohlpaintner, Philipp J.; Wiebe, Anton; Breinbauer, Rolf; Schollmeyer, Dieter & Waldvogel, Siegfried R.