Electrochemical Trifluoromethylthiolation and Spirocyclization of Alkynes with AgSCF3: Access to SCF3-Containing Spiro[5,5]trienones

A novel and efficient strategy for trifluoromethylthiolation and dearomatization of activated alkynes with stable and readily available AgSCF3 has been developed. Reported herein is the unprecedented electrochemical generation of the SCF3 radical in the absence of persulfate for the synthesis of SCF3-containing spiro[5,5]trienones in good yields via a 6-exo-trig radical cyclization.

Automated summary

A novel and efficient strategy has been developed for trifluoromethylthiolation and dearomatization of activated alkynes using stable and readily available AgSCF3. The unprecedented electrochemical generation of the SCF3 radical enables the synthesis of SCF3-containing spiro[5,5]trienones in good yields via a 6-exo-trig radical cyclization.