Solvent Control in Electro-Organic Synthesis

Lara Schulz; Siegfried R. Waldvogel

doi:10.1055/s-0037-1610303

Synlett, Table of Contents

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

,

Siegfried R. Waldvogel *

Institut für Organische Chemie, Johannes Gutenberg-Universität Mainz, Duesbergweg 10–14, 55128 Mainz, Germany Email: waldvogel@uni-mainz.de

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Abstract

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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

Key words

C–C coupling - electrochemical fluorination - electrosynthesis - Kolbe electrolysis - N–C coupling - solvent effect - 1,1,1,3,3,3-hexafluoropropan-2-ol

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References

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