Expedient synthesis of tetrafluorophenoxthiines and derivatives by copper(I)-catalyzed cross-coupling reaction

• Tetrafluorophenoxthiines were successfully synthesized.
• A notable mode of CF bond activation.
• Providing an efficient method to build up S, O-heterocycles.

In this research, tetrafluorophenoxthiines were successfully synthesized from pentafluorobenzene and aryl thiols or diaryl disulfides in the presence of copper catalyst and ligand by using O2 as the oxidant, t-BuOLi as the base at 100 °C. The ligand (E)-3-(dimethylamino)-1-(2-hydroxyphenyl)prop-2-en-1-one (L) played an indispensable role in the reaction. This work contains a notable mode of CF bond activation, which is in the ortho position to the CH bond of pentafluorobenzene.

A novel type of cross-coupling reaction of pentafluorobenzene with thiols or diaryl disulfides for the formation of S, O-heterocycles has been briefly developed. The advantages of the novel procedure contains a notable mode of CF bond activation, which is in the ortho position to the CH bond of pentafluorobenzene.Figure optionsDownload as PowerPoint slide