Trifluoromethylthiolation of α-Chloroaldehydes: Access to Quaternary SCF3-Containing Centers
Résumé
In this study, a straightforward methodology was developed to access quaternary α‐trifluoromethylthiolated chloroaldehydes. Using the Munavalli reagent as the electrophilic SCF3 source, a base‐catalyzed trifluoromethylthiolation reaction with a panel of α‐chloroaldehydes was successfully achieved under mild reaction conditions. The α‐trifluoromethylthiolated chloroaldehydes were obtained in moderate to high yields (up to 88 %). This approach demonstrated a good functional‐group tolerance and offered access to highly functionalized quaternary trifluoromethylthiolated aldehydes, inaccessible so far. The development of an enantioselective version was investigated by using a chiral phase‐transfer catalyst, giving the enantioenriched product in moderate enantiomeric excess.