Fakultät für Chemie und Pharmazie

Electrophilic thioether synthesis starting from organozinc reagents

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

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.

 

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