Trifluoromethylthiolation of α-Chloroaldehydes: Access to Quaternary SCF3 -Containing Centers

Abstract

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.