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

摘要

[alpha]-Chloroalkyl phenyl sulfides 1 readily insert zinc in THF at 25 [deg]C (0.5-2 h), affording sulfur stabilized organozinc derivatives of type 2. 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 reagent 3, they react with a wide range of electrophiles. Zinc and copper organometallics bearing a thiophenyl or a phenylsulfinyl group at the [gamma]-position have also been prepared showing the generality of our approach.