1045821-71-3Relevant academic research and scientific papers
Multigram Scale Syntheses of First and Second Generation of Trifluoromethanesulfenamide Reagents
Glenadel, Quentin,Alazet, Sébastien,Baert, Fran?ois,Billard, Thierry
, p. 960 - 964 (2016)
Trifluoromethanesulfenamide reagents constitute a family of very efficient reagents to trifluoromethylthiolate various molecules. Optimized syntheses have been developed to easily obtain, in a reproducible manner, large quantities of these reagents, with good overall yields. Up to 84 g have already been obtained, at a reasonable cost.
Palladium-Catalyzed Trifluoromethylthiolation of Chelation-Assisted C–H Bonds
Kesavan, Arunachalam,Chaitanya, Manthena,Anbarasan, Pazhamalai
supporting information, p. 3276 - 3279 (2018/07/13)
An efficient palladium-catalyzed trifluoromethylthiolation of chelation-assisted C–H bonds has been accomplished by employing a readily accessible trifluoromethylthiolating reagent. The reaction tolerates various directing groups and functional groups and allows the access to diverse trifluoromethylthiolated arenes in good yield. A plausible mechanism was proposed based on preliminary mechanistic investigations.
For the production of sulfur-hydrogen reagent, synthetic method and its application
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Paragraph 0142-0144, (2017/09/26)
The invention discloses a trifluoromethylthio reagent as well as a synthetic method and application thereof and provides a compound I and a preparation method of the compound I. The preparation method comprises the step: reacting a compound 1a with trifluoromethylthio silver, so as to obtain the compound 1, wherein the reaction is as shown in the specification. The invention further provides application of the compound 1 as the trifluoromethylthio reagent. The compound 1 can react with amine compounds, thiol or phenolic compounds to generate the compound containing trifluoromethylthio. The trifluoromethylthio reagent 1 has the beneficial effects of high efficiency, conversion rate and yield, mild reaction conditions, low production cost and wide applicable range and is applicable to industrial production.
Selective and scalable synthesis of trifluoromethanesulfenamides and fluorinated unsymmetrical disulfides using a shelf-stable electrophilic SCF3 reagent
Pluta, Roman,Rueping, Magnus
supporting information, p. 17315 - 17318 (2015/02/19)
The chemoselective trifluoromethylthiolation of nitrogen nucleophiles and thiols using N-(trifluorome-thylthio)phthalimide under mild, metal-free conditions is described. A series of trifluoromethanesulfenamides and unsymmetrical disulfides is prepared from the corresponding aliphatic and aromatic amines and thiols in good yields. The reactions are operationally simple and tolerate a wide variety of functional groups. Trifluoromethanesulfenamides and disulfides belong to interesting classes of organic molecules which possess remarkable properties for medicinal and agrochemical applications.
N-trifluoromethylthiosaccharin: An easily accessible, shelf-stable, broadly applicable trifluoromethylthiolating reagent
Xu, Chunfa,Ma, Bingqing,Shen, Qilong
supporting information, p. 9316 - 9320,5 (2014/10/15)
A new, electrophilic trifluoromethylthiolating reagent, N-trifluoromethylthiosaccharin, was developed and can be synthesized in two steps from saccharin within 30minutes. N-trifluoromethylthiosaccharin is a powerful trifluoromethylthiolating reagent and allows the trifluoromethylthiolation of a variety of nucleophiles such as alcohols, amines, thiols, electron-rich arenes, aldehydes, ketones, acyclic β-ketoesters, and alkynes under mild reaction conditions. 'Sacch'ed out: A new, electrophilic trifluoromethylthiolating reagent, N-trifluoromethylthiosaccharin (1) can be synthesized in two steps from saccharin within 30minutes. The reagent 1 allows the trifluoromethylthiolation of a variety of nucleophiles such as alcohols, amines, thiols, electron-rich arenes, aldehydes, ketones, acyclic β-ketoesters, and alkynes under mild reaction conditions.
Direct electrophilic N-trifluoromethylthiolation of amines with trifluoromethanesulfenamide
Alazet, Sebastien,Ollivier, Kevin,Billard, Thierry
supporting information, p. 2354 - 2357 (2014/01/06)
The CF3SN moiety is a substituent with interesting properties. However, there is no easy synthetic access to molecules bearing this group. The trifluoromethanesulfenamide is a new reagent for the electrophilic trifluoromethylthiolation which reacts easily with amines to obtain trifluoromethylsulfanylamines with good yields.
Sequential electrophilic trifluoromethanesulfanylation-cyclization of tryptamine derivatives: Synthesis of C(3)-trifluoromethanesulfanylated hexahydropyrrolo[2,3-b]indoles
Yang, Yi,Jiang, Xueliang,Qing, Feng-Ling
, p. 7538 - 7547 (2012/11/07)
A practical and efficient synthesis of C(3)-trifluoromethanesulfanylated hexahydropyrrolo[2,3-b]indoles 5 from tryptamine derivatives was described. The features of this synthesis included electrophilic activation of C(3) of tryptamine derivatives with CF3S+ ? and cascade ring cyclization by carbamate nucleophile attacking at C(2). Surprisingly, when Lewis acid (BF3·OEt2) was used as activator instead of proton acid (TsOH·H2O) for the electrophilic trifluoromethanesulfanylation of tryptamine derivatives, the uncyclized product 6 was formed preferentially. This sequential trifluoromethanesulfanylation- cyclization protocol was used to synthesize several pyrrolidinoindolinic alkaloid analogues. The cytotoxicity activities of these trifluoromethanesulfanylated alkaloid analogues were evaluated against three cancer cell lines (K562, HeLa, L929).
Synthesis of trifluoromethanesulfinamidines and -sulfanylamides
Ferry, Aurelien,Billard, Thierry,Langlois, Bernard R.,Bacque, Eric
supporting information; experimental part, p. 9362 - 9365 (2009/04/11)
(Chemical Equation Presented) Fluorinated moieties constitute important substituents used in many applications to modify the properties of molecules. The action of DAST onto Ruppert's reagent yields to a not isolable intermediate that can then react with various primary amines to give trifluoromethanesulfinamidines and trifluoromethane-sulfanylamides. Such compounds were unknown until now and constitute interesting new families of fluorinated molecules.
