4.8 Article

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

Journal

ORGANIC LETTERS
Volume 23, Issue 17, Pages 6691-6696

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c02260

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Funding

  1. National Natural Science Foundation of China [22071171]
  2. Natural Science Foundation of the Jiangsu Higher Education Institutions of China [19KJB150020]

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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.
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.

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