The Chan-Lam-type synthesis of thioimidazolium salts for thiol-(hetero)arene conjugation.

The design of stable and variable aryl linkers for conjugating drug moieties to the metabolism-related thiols is of importance in drug discovery. We disclosed that thioimidazolium groups are unique scaffolds for the thiol-(hetero)arene conjugation under mild conditions. The drug bound thioimidazolium salts, which are easily accessible via a copper-mediated Chan-Lam process in gram-scale, could be successfully applied to the late-stage coupling of bioactive thiols to construct a broad array of drug-like molecules.

Copper-Mediated Deconstructive Ring Cleavage of Cyclic Thioethers with Boron Compounds.

The deconstructive ring cleavage of cyclic thioethers is achieved through a Chan-Lam type process with boron compounds. The sequential hydroboration/ring cleavage process from alkynes offered a new route to the preparation of vinyl sulfides based on the developed conditions. Further exploration has demonstrated the versatility of nucleophiles, delivering various functionalized sulfides featuring linear frameworks.