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

Grassl, Simon; Hamze, Clemente; Koller, Thaddaeus J. und Knochel, Paul (2019): Copper-Catalyzed Electrophilic Thiolation of Organozinc Halides by Using N-Thiophthalimides Leading to Polyfunctional Thioethers. In: Chemistry-A European Journal, Bd. 25, Nr. 15: S. 3752-3755

Abstract

(Hetero)aryl, benzylic, and alkyl zinc halides were thiolated with N-thiophthalimides at 25 degrees C within 1h in the presence of 5-10% Cu(OAc)(2)H2O 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.

• Dokumententyp: Zeitschriftenartikel
• Fakultät: Chemie und Pharmazie > Department Chemie
• Themengebiete: 500 Naturwissenschaften und Mathematik > 540 Chemie
• ISSN: 0947-6539
• Sprache: Englisch