Here, we report the modular synthesis of trifluoromethylated/difluoromethylated dihydroquinoline sulfonyl fluorides via 4 + 2 cycloadditions of o-aminotrifluoroacetophenone derivatives or o-aminodifluoroacetophenone derivatives with 2-chloroprop-2-ene-1-sulfonyl fluoride (CESF) under mild reaction conditions. Subsequent sulfur(VI) fluoride exchange was subjected to optimization for nucleophiles based on nitrogen and oxygen, furnishing sulfonamides and sulfonates, respectively. The reaction is accomplished without employing transition metal catalysts, yielding novel products that hold significant potential in the fields of medicinal chemistry, chemical biology, and drug discovery.
Zou et al. (Wed,) studied this question.