0000000000141607
AUTHOR
Aaron Schüll
Metal-free electrochemical fluorodecarboxylation of aryloxyacetic acids to fluoromethyl aryl ethers
Electrochemical decarboxylation of aryloxyacetic acids followed by fluorination provides easy access to fluoromethyl aryl ethers. This electrochemical fluorodecarboxylation offers a sustainable approach with electric current as traceless oxidant. Using Et3N·5HF as fluoride source and as supporting electrolyte, this simple electrosynthesis affords various fluoromethoxyarenes in yields up to 85%.
About the selectivity and reactivity of active nickel electrodes in C–C coupling reactions
Active anodes which are operating in highly stable protic media such as 1,1,1,3,3,3-hexafluoroisopropanol are rare. Nickel forms, within this unique solvent, a non-sacrificial active anode at constant current conditions, which is superior to the reported powerful molybdenum system. The reactivity for dehydrogenative coupling reactions of this novel active anode increases when the electrolyte is not stirred during electrolysis. Besides the aryl-aryl coupling, a dehydrogenative arylation reaction of benzylic nitriles was found while stirring the mixture providing quick access to synthetically useful building blocks.
CCDC 1976461: Experimental Crystal Structure Determination
Related Article: Sebastian B. Beil, Manuel Breiner, Lara Schulz, Aaron Schüll, Timo Müller, Dieter Schollmeyer, Alexander Bomm, Michael Holtkamp, Uwe Karst, Wolfgang Schade, Siegfried R. Waldvogel|2020|RSC Advances|10|14249|doi:10.1039/D0RA02673E