Efficient Synthesis of Aryl Methyl Sulfide Derivatives Using (Methylthio)trimethylsilane as Methylthiolation Reagent

The synthesis of various aryl methyl sulfides has been achieved by treatment of nitroarenes with a combination of (methylthio)trimethylsilane and cesium carbonate in dimethylsulfoxide. This reaction gives access to aryl methyl sulfide derivatives in high yields.     

Preparation of functionalized zinc and copper organometallics containing sulfur functionalities at the alpha or gamma position

-Chloroalkyl phenyl sulfides1 readily insert zinc in THF at 25 °C (0.5–2 h), affording sulfur stabilized organozinc derivatives of type2. The presence of a functional group such as an ester or a cyano group is tolerated in these organometallics. After a transmetallation to the corresponding copper reagent3, they react with a wide range of electrophiles. Zinc and copper organometallics bearing a thiophenyl or a phenylsulfinyl group at the γ-position have also been prepared showing the generality of our approach.