Electrochemical Sulfonylation of Electron-Rich Aromatic Substrates with Sodium Sulfinates
At a Glance
Section titled âAt a Glanceâ| Metadata | Details |
|---|---|
| Publication Date | 2020-05-01 |
| Journal | ECS Meeting Abstracts |
| Authors | Joachim Nikl, Sebastian Lips, Siegfried R. Waldvogel |
| Institutions | Merck (Germany), Johannes Gutenberg University Mainz |
Abstract
Section titled âAbstractâThe use of electricity in organic synthesis is characterized by various advantages over conventional methods in terms of reaction selectivity, safety, and sustainability. [1] The use of electrons as reagents, as well as precise reaction control, allows direct C-H bond activation, resulting in less reagent waste. The combination of supporting electrolyte and coupling component, therefore, has a particularly positive effect on the atomic efficiency. Regarding this, we present an electrochemically driven synthesis of various aryl and diaryl sulfones, [2] which amongst others are an important structural motif in pharmaceutical active ingredients. [3] This electrochemical protocol, based on boron-doped diamond electrodes (BDD) and 1,1,1,3,3,3âhexafluoropropanâ2âol (HFIP) as solvent, leads to a direct C-S coupling of electron-rich aromatic substrates with sodium sulfinates. The last ones are used combinatorially as supporting electrolytes and coupling components, which makes this method a sustainable contribution to the organic synthesis of sulfones. References [1] a) H. J. SchĂ€fer, C. R. Chim. 2011, 14 , 745- 765; b) A. Wiebe, T. Gieshoff, S. Möhle, E. Rodrigo, M. Zirbes, S. R. Waldvogel, Angew. Chem. Int. Ed. 2018, 57 , 5594- 5619; Angew. Chem. 2018, 130 , 5694- 5721. [2] a) J. Nikl, S. Lips, D. Schollmeyer, R. Franke, S. R. Waldvogel, Chem. - Eur. J. 2019 , 25 , 6891-6895; b) J. Nikl, D. Ravelli, D. Schollmeyer , S. R. Waldvogel, ChemElectroChem. 2019 , 6 , 4450-4455. [3] a) M. Feng, B. Tang, S. H. Liang, X. Jiang, Curr. Top. Med. Chem. 2016, 16 , 1200- 1216; b) D. C. Meadows, J. Gervay-Hague, Med. Res. Rev. 2006, 26 , 793- 814. Figure 1