Selective electrochemical fluorination of O,S‐acetal derivatives bearing α‐electron‐withdrawing groups

Abstract

AbstractIn order to perform selective fluorination of organic molecules, conventional hazardous fluorinating reagents have been mainly employed so far. However, selective electrochemical fluorination does not require any hazardous reagents. Herein, we present electrochemical fluorination of O,S‐acetals bearing electron‐withdrawing ester, amide, and nitrile groups at their α‐positions using various supporting poly(HF) salts such as Et3N‐nHF (n = 3–5) and Et4NF‐nHF (n = 3–5). In the case of O,S‐acetals bearing an ester group, the corresponding α‐fluorination products and/or fluorodesulfurization products were formed selectively depending on supporting poly(HF) salts used. O,S‐Acetals bearing a relatively weak electron‐withdrawing amide group gave fluorodesulfurization products selectively while O,S‐acetal having a strongly electron‐withdrawing nitrile group provided the α‐fluorinated product predominantly regardless of the poly(HF) salts used.