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RESEARCH PRODUCT

(Organic and Biological Electrochemistry Division Manuel M. Baizer Award Address) Making Electroorganic Synthesis More Practical

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The direct use of electrochemistry for the generation of reactive intermediates can have major advantages towards conventional synthetic strategies.[1] Less or no reagent waste is generated and new reaction pathways are accessible.[2] In order to exploit the electricity driven conversions for synthetic purposes and to install unique selectivity two modern approaches will be outlined: Solvent-controlled selective dehydrogenative cross-coupling reactions: A key for this is the use of boron-doped diamond anodes and fluorinated alcohols within the electrolyte.[3] This methodology opened new pathways for innovative and scalable arylation reactions.[4] New electrode systems for the anodic and cathodic conversion to value-added organic compounds. These systems are capable to go beyond common limits in electro-organic synthesis. The working horse to identify suitable electrolytic conditions is the electrosynthetic screening approach. This strategy gives also rise to fast optimization and subsequent scale-up.[5] In particular, the second approach will deal with concepts which represent milestones originating from the Baizer process. References: [1] E.J. Horn, B.R. Rosen, P.S. Baran, ACS Cent. Sci. 2 (2016) 302-307. [2] a) S. Möhle, M. Zirbes, E. Rodrigo, T. Gieshoff, A. Wiebe, S. R. Waldvogel, Angew. Chem. Int. Ed. 57 (2018) 6018-6041; b) A. Wiebe, T. Gieshoff, S. Möhle, E. Rodrigo, M. Zirbes, S. R. Waldvogel, Angew. Chem. Int. Ed. 57 (2018) 5594-5619. [3] L. Schulz, S.R. Waldvogel, Synlett 30 (2019) 275-286. [4] S.R. Waldvogel, S. Lips, M. Selt, B. Riehl, C.J. Kampf, Chem. Rev., 118 (2018) 6706-6765. [5] C. Gütz, B. Klöckner, S.R. Waldvogel, Org. Process Res. Dev. 20 (2016) 26-32.