CC BY-ND-NC 4.0 · Synlett 2019; 30(03): 275-286
DOI: 10.1055/s-0037-1610303
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Solvent Control in Electro-Organic Synthesis

Lara Schulz
,
Institut für Organische Chemie, Johannes Gutenberg-Universität Mainz, Duesbergweg 10–14, 55128 Mainz, Germany   eMail: [email protected]
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S.R.W thanks the DFG Wa1276/17-1 for financial support. The authors highly appreciate the financial support by the Center for INnovative and Emerging MAterials (CINEMA) and the support by BMBF-EPSYLON (FKZ 13XP5016D).
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Publikationsverlauf

Received: 03. September 2018

Accepted after revision: 17. September 2018

Publikationsdatum:
13. Dezember 2018 (online)


Abstract

Exploiting the solvent control within electro-organic conversions is a far underestimated parameter in prep-scale electrolysis. The beneficial application in several transformations is outlined and in particular discussed for the dehydrogenative coupling of arenes and heteroarenes. This simple electrolytic strategy in fluorinated solvents allows the modulation of the substrate’s nucleophilicity and the stabilization of the intermediates as well as of the final product from over-oxidation.

1 Introduction

2 Solvent Effects in Kolbe Electrolysis and Anodic Fluorination

3 Unique Solvent Effects of 1,1,1,3,3,3-Hexafluoropropan-2-ol (HFIP)

4 Anodic Dehydrogenative Coupling Reactions with Use of HFIP as the Solvent

5 Conclusion

 
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