Electrophilic thioether synthesis starting from organozinc reagents

Mar 11, 2019

LMU chemists have developed a versatile method for the synthesis of highly functionalized thioethers. This building block is widely used in, among other things, biologically active substances.

Illustrated representation of electrophilic thioether synthesis (Image: Peter Dowling)

Under the direction of Prof. Paul Knochel, the doctoral student Simon Graßl has developed a robust and versatile electrophilic synthesis of thioethers. The synthon of the thioether is a widely used functional group and is represented among others in various biologically active substances, pharmaceuticals and organic semiconductors.

For the described method, N-thiophthalimides were used as an electrophilic sulfur source and reacted under copper catalysis with organozinc Regenzien. Only small amounts of copper (II) acetate monohydrate were needed as a catalyst. In addition to a large number of different thioethers, this method could also initiate the introduction of small highly functional groups such as thiotrifluoromethyl (-SCF3) or thiocyanates (-SCN).

These results appeared in the journal Chemistry - A European Journal as Cover Feature / Hot Paper.

Publication: Chemistry - A European Journal