Electrolytic partial fluorination of organic compounds. 33. Regioselective anodic monofluorination of α-phenylsulfenyl lactams and sulfur-containing nitrogen heterocycles

Abstract

Anodic monofluorination of a variety of nitrogen heterocycles has been investigated in order to ascertain the scope and limitations of the anodic monofluorination method in the synthesis of monofluorinated nitrogen heterocycles. Electrolytic monofluorination of α-(phenylsulfenyl)lactams proceeded effectively, and the regiochemistry and efficiency of the reaction were greatly dependent on the molecular structure (ring size, substitution on the nitrogen atom, etc.) of the lactams. The high yields of monofluorinated lactams observed here are of great synthetic value because the phenylsulfenyl group is known to be easily removed oxidatively and/or reductively.