E-SONATA  Electrochemical incorporation of SO2 and late-stage functionalization of complex molecules

E-SONATA (Electrochemical incorporation of SO2 and late-stage functionalization of complex molecules)

Organic molecules with sulfonyl(-SO2-) functionalities are widely used in pharmaceutical chemistry as these groups have unique biological activities. The development of new ways to synthesize these valuable molecules is therefore of academic as well as technical interest.

In recent years, a strong focus has been placed on the synthesis of SO2 functionality through the direct incorporation of SO2. To avoid the handling of gaseous SO2, SO2 surrogates are usually used as easy-to-handle substitutes. However, this is associated with high costs and low atomic efficiency. Stock solutions of SO2 in polar solvents are a good alternative. From these stock solutions, the SO2 can then be incorporated directly into organic molecules, but selectivity during incorporation has so far been low.

A particularly high selectivity in the incorporation of SO2 from stock solutions can be achieved by a combination of electrochemistry under solvent control. The reactivity of the oxygen in the SO2 is suppressed, e.g. by fluorinated alcohols, and only the sulphur is selectively incorporated into the desired molecule. By using different nucleophiles, a broad spectrum of different relevant groups such as sulfones, sulfonamides or sulfonates can be generated.

The E-SONATA network aims to create efficient access to these valuable structural motifs by combining the know-how of the universities in Mainz and Kaiserslautern for the reagent-free incorporation of SO2 into highly functionalized molecules.

Coordinator:

Siegfried R. Waldvogel (MPI CEC) siegfried.waldvogel@cec.mpg.de

Georg Manolikakes (RPTU) manolikakes@chemie.uni-kl.de