Electrochemical fluorination of aliphatic aldehydes and cyclic ketones using Et 3N-5HF electrolyte

Abstract

The first electrochemical oxidative fluorination of aliphatic aldehydes ( 1) and cyclic ketones ( 3) has been successfully carried out using Base-HF as the supporting electrolyte and fluorine source. The selective displacement of formyl hydrogen by fluorine in aliphatic aldehydes electrochemically took place to give acyl fluorides ( 2) in good yields in the presence of the Et 3N-5HF electrolyte. On the other hand, the selective α-bond cleavage between the carbonyl carbon and substituted α-carbon in cyclic ketones occurred in the presence of the Et 3N-5HF electrolyte to give fluoroacyl fluorides ( 4), which were readily converted in good yields to the corresponding fluorocarboxylic esters ( 5) by the subsequent alcoholysis.