1423403-27-3Relevant academic research and scientific papers
Activation of Trifluoromethylthio Moiety by Appending Iodonium Ylide under Copper Catalysis for Electrophilic Trifluoromethylation Reaction
Saidalimu, Ibrayim,Suzuki, Shugo,Tokunaga, Etsuko,Shibata, Norio
supporting information, p. 485 - 489 (2016/05/24)
A novel iodonium-ylide compound 2 that appends atrifluoromethylthio (SCF3) group is disclosed as a new, shelf-stable electrophilic trifluoromethylation reagent. Unlike known shelf-stable electrophilic trifluoromethylation reagents, 2 has a stable SCF3 group which is activated by appending iodonium ylide under copper catalysis via sulfonium ylide to generate a cationic trifluoromethyl (CF3) species. Reagent 2 was found to be an efficient electrophilic trifluoromethylation reagent for a wide range of silyl enol ethers 3 under copper catalysis. Cyclic and acyclic α-trifluoromethyl ketones 4 were obtained by reagent 2 in moderate to good yields. On the other hand, a difluoromethylthio analogue 5 did not affect intermolecular transfer difluoromethylation to substrates. Instead, intramolecular 1,4-migration proceeded similar to the Stevens rearrangement to provide 6 in 21% yield, independent of the presence of nucleophiles 3.
Synthesis of α-trifluoromethyl ketones via the Cu-catalyzed trifluoromethylation of silyl enol ethers using an electrophilic trifluoromethylating agent
Li, Lun,Chen, Qing-Yun,Guo, Yong
supporting information, p. 5145 - 5152 (2014/06/23)
A method has been developed for the synthesis of α-trifluoromethyl ketones via the Cu-catalyzed trifluoromethylation of silyl enol ethers with an electrophilic trifluoromethylating agent, which produces a trifluoromethyl radical.
