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- Title
Copper‐Catalyzed Electrophilic Thiolation of Organozinc Halides by Using N‐Thiophthalimides Leading to Polyfunctional Thioethers.
- Authors
Graßl, Simon; Hamze, Clémence; Koller, Thaddäus J.; Knochel, Paul
- Abstract
(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⋅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. (Hetero)aryl, benzylic, and alkyl zinc halides were thiolated with N‐thiophthalimides at 25 °C in the presence of 5–10 % Cu(OAc)2⋅H2O to give polyfunctionalized thioethers in 55–98 % yields (see scheme). 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 the seven‐step synthesis of a potent cathepsin D inhibitor in 34 % overall yield.
- Subjects
PALLADIUM; SULFIDES; ZINC halides; HALIDES
- Publication
Chemistry - A European Journal, 2019, Vol 25, Issue 15, p3752
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201900758