946-65-6Relevant academic research and scientific papers
Electrochemical Trifluoromethylation of Thiophenols with Sodium Trifluoromethanesulfinate
Zhu, Xing-Xing,Wang, Huai-Qin,Li, Chen-Guang,Xu, Xiao-Lan,Xu, Jun,Dai, Jian-Jun,Xu, Hua-Jian
, p. 16114 - 16120 (2021/02/03)
We developed an electrochemical trifluoromethylation of thiophenols without the use of metal catalysts and oxidants. This reaction features mild reaction conditions, readily available substrate, as well as moderate to good yields. In addition, this protocol can be easily scaled up with moderate efficiency.
Copper-Catalyzed Trifluoromethylthiolation of Di(hetero)aryl-λ3-iodanes: Mechanistic Insight and Application to Synthesis of (Hetero)Aryl Trifluoromethyl Sulfides
Saravanan, Perumal,Anbarasan, Pazhamalai
supporting information, p. 3521 - 3528 (2016/01/25)
The direct and regioselective copper/S-Phos-catalyzed trifluoromethylthiolation of symmetrical and unsymmetrical di(hetero)aryl-λ3-iodanes has been accomplished for the synthesis of various (hetero)aryl trifluoromethyl sulfides employing readily accessible silver trifluoromethylthiolate (AgSCF3) as nucleophilic trifluoromethylthiolating reagent. The developed transformation tolerates various functional groups like nitrile, enolizable ketone, ester, nitro and free carboxylic acid. Interestingly, the formal trifluoromethylthiolation of arenes was also achieved through integration of the synthesis of diaryl-λ3-iodanes from arenes with the trifluoromethylthiolation. Mechanistic investigations did not favor the radical formation and SET pathway. Based on the variable temperature 19F NMR spectroscopy, isolation of the most relevant catalytic intermediate, and stoichiometric studies supported the Cu(I)/Cu(III) catalytic cycle, wherein the oxidative addition of diaryl-λ3-iodanes was assisted by the silver salt.
Sandmeyer trifluoromethylthiolation of arenediazonium salts with sodium thiocyanate and Ruppert-Prakash reagent
Danoun, Gregory,Bayarmagnai, Bilguun,Gruenberg, Matthias F.,Goossen, Lukas J.
, p. 1312 - 1316 (2014/03/21)
In the presence of copper thiocyanate, sodium thiocyanate and the inexpensive, easy-to-use trifluoromethylating reagent Me3Si-CF 3, diazonium salts are smoothly converted into the corresponding aryl trifluoromethyl thioethers. Combin
Novel reactions of perfluoroalkylphenyl sulfides with organolithium reagents
Munavalli, S.,Hassner, A.,Rossman, D. I.,Singh, S.,Rohrbaugh, D. K.,Ferguson, C. P.
, p. 7 - 12 (2007/10/02)
The reaction of anisole with organolithium reagents, commonly known as ortho-directed metallation, is of considerable synthetic utility in organic chemistry and as such has attracted considerable attention in recent years.Over the past 50 years, several mechanisms have been proposed to account for the observed regioselective metallation.For the first time, the reaction of perfluoroalkylphenyl sulfides with organolithium reagents has been investigated and found to furnish products resulting from the replacement of the perfluoroalkyl moieties with alkyl groups derived from the metallating agents.Phenyltrifluoromethyl ether, the anisole analog, failed to undergo metallation.A rationalization for the formation of unusual products via mediation of a single-electron-transfer process is presented in this paper together with the spectral data of the products. - Keywords: Reactions; Perfluoroalkylphenyl sulfides; Organolithium reagents; NMR spectroscopy; Mass spectrometry; Orthometallation
Process for preparing aryl trifluoromethylsulfides
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, (2008/06/13)
Trifluoromethylthiocopper, formed in situ by the reaction of bis-(trifluoromethylthio)mercury with copper, reacts with aromatic bromides and iodides to give aryl trifluoromethyl sulfides.
