Electrooxidative Synthesis of Bis- and Oligoarenes
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
- 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
(See online at https://doi.org/10.1002/anie.201604321) - 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
(See online at https://doi.org/10.1002/anie.201605865) - 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
(See online at https://doi.org/10.1055/s-0036-1588610) - 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
(See online at https://doi.org/10.1002/anie.201612613) - 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
(See online at https://doi.org/10.1002/anie.201708946) - 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
(See online at https://doi.org/10.1021/acscatal.6b03090) - 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
(See online at https://doi.org/10.1126/sciadv.aao3920) - 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
(See online at https://doi.org/10.1055/s-0037-1611942) - 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
(See online at https://doi.org/10.1002/chem.201805737)
