Copper-Catalyzed Electrophilic Thiolation of Organozinc Halides by Using N-Thiophthalimides Leading to Polyfunctional Thioethers.

(Hetero)aryl, benzylic, and alkyl zinc halides were thiolated with N-thiophthalimides at 25 °C within 1 h in the presence of 5-10 % Cu(OAc)2 ⋅H2 O to furnish the corresponding polyfunctionalized thioethers in good yields. This electrophilic thiolation was extended to the introduction of trifluoromethylthio (SCF3 ), thiocyanate (SCN), and selenophenyl (SePh) groups. The utility of this method was shown in a seven-step synthesis of a potent cathepsin D inhibitor in 34 % overall yield.