Monofluoromethyl-Substituted Sulfonium Ylides: Electrophilic Monofluoromethylating Reagents with Broad Substrate Scopes

Two electrophilic monofluoromethylating reagents S-monofluoromethyl-S-phenyl-bis(carbomethoxy) methylide sulfonium ylide 3a and S-monofluoromethyl-S-(4-nitrophenyl)-bis(carbo -methoxy) methylide sulfonium ylide 3b and their reactions with a variety of nucleophiles such as alcohols and malonate derivatives, sulfonic and carboxylic acids, phenols, amides, and nitrogen of heteroarenes under mild conditions were described. Mechanistic studies by employing deuterated reagents 3a-D2/3b-D2 suggest that these monofluoromethylating reactions proceed via an electrophilic substitution pathway.