- Synthesis method of silver(I) trifluoromethanethiolate
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The invention belongs to the technical field of synthesis of organic compounds, and relates to a synthesis method of silver(I) trifluoromethanethiolate. According to the synthesis method of silver(I) trifluoromethanethiolate (CAS number: 811-68-7) in the invention, silver fluoride is used as a raw material and trifluoromethylthioester is used as a trifluoromethylthio source so as to synthesize silver(I) trifluoromethanethiolate. According to the method, trifluoromethylthioester is used as the trifluoromethylthio source and reacts with the silver fluoride in a solvent to generate silver(I) trifluoromethanethiolate, and a finished silver(I) trifluoromethanethiolate product is obtained after separation and purification. According to the synthesis method of silver(I) trifluoromethanethiolate, raw materials are easy to obtain, reaction reagents are easy to prepare and low in price, the synthesis cost of silver(I) trifluoromethanethiolate is remarkably reduced, synthesis conditions are mild, operation is easy, convenient and safe, industrial production is facilitated, the utilization rate of silver atoms is high, and environmental protection is realized.
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Paragraph 0014-0018
(2021/05/12)
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- Ammonium Chloride-Mediated Trifluoromethylthiolation of p-Quinone Methides
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Ammonium chloride-mediated trifluoromethylthiolation of p-quinone methides is reported using inexpensive and bench stable AgSCF3 as a nucleophilic trifluoromethylthiolating (-SCF3) reagent. This method is an efficient strategy for the construction of the benzylic C(sp3)-SCF3 bond to synthesize trifluoromethylthio-diarylmethane derivatives by 1,6-conjugate addition/aromatization under mild reaction conditions without any metal catalyst, oxidants, or additives. This is the first report of trifluoromethylthiolation of p-quinone methides. In addition, di-trifluoromethylthiolation of δ-chloro-p-quinone methide and scalability are demonstrated.
- Das, Debabrata,Ghosh, Krishna Gopal,Chandu, Palasetty,Sureshkumar, Devarajulu
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p. 14201 - 14209
(2020/11/13)
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- N-Trifluoromethylthiolated Sulfonimidamides and Sulfoximines: Anti-microbial, Anti-mycobacterial, and Cytotoxic Activity
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Herein we demonstrate the expanded utility of a recently described N-trifluoromethylthiolation protocol to sulfonimidamide containing substances. The novel N-trifluoromethylthio sulfonimidamide derivatives thus obtained were evaluated for antibacterial activity against Mycobacterium tuberculosis (M. tb.) and Mycobacterium abscessus and Gram + Ve (Streptococcus aureus, Bacillus subtilis), and Gram - Ve (Escherichia coli, Pseudomonas aeruginosa) bacteria. Two compounds, 13 and 15 showed high antimycobacterial activity with MIC value of 4-8 μg/mL; i.e. comparable to WHO recommended first line antibiotic for TB infection ethambutol. The same compounds were also found to be cytotoxic in HepG2 cells (compound 13 IC50 = 15 μg/mL; compound 15 IC50 = 65 μg/mL). A structure activity relationship, using matched pair analysis, gave the unexpected conclusion that the trifluoromethylthio moiety was responsible for the cellular and bacterial toxicity. Given the increasing use of the trifluoromethylthio group in contemporary medicinal chemistry, this observation calls for considerations before implementation of the functionality in drug design.
- Thota, Niranjan,Makam, Parameshwar,Rajbongshi, Kamal K.,Nagiah, Savania,Abdul, Naeem Sheik,Chuturgoon, Anil A,Kaushik, Amit,Lamichhane, Gyanu,Somboro, Anou M.,Kruger, Hendrik G.,Govender, Thavendran,Naicker, Tricia,Arvidsson, Per I
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supporting information
p. 1457 - 1461
(2019/10/11)
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- Direct sequential C-H iodination/organoyl-thiolation for the benzenoid A-ring modification of quinonoid deactivated systems: A new protocol for potent trypanocidal quinones
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We report a sequential C-H iodination/organoyl-thiolation of naphthoquinones and their relevant trypanocidal activity. Under a combination of AgSR with a copper source, sulfur-substituted benzenoid quinones were prepared in high yields (generally >90%). This provides an efficient and general method for preparing A-ring modified naphthoquinoidal systems, recognized as a challenge in quinone chemistry.
- Jardim, Guilherme A. M.,Oliveira, Willian X. C.,De Freitas, Rossimiriam P.,Menna-Barreto, Rubem F. S.,Silva, Thaissa L.,Goulart, Marilia O. F.,Da Silva Júnior, Eufranio N.
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supporting information
p. 1686 - 1691
(2018/03/21)
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- Organocatalytic Α-trifluoromethylthiolation of silylenol ethers: Batch vs continuous flow reactions
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This work describes the organocatalytic α-trifluoromethylthiolation of silylenol ethers using N-(trifluoromethylthio)saccharin as trifluoromethylthiolating reagent that is activated by the presence of catalytic amounts of a Lewis base. Tetrahydrothiophene was identified as the best organocatalyst and it was successfully employed to promote the synthesis of different α-trifluoromethylketones; the reaction has been performed under a traditional batch methodology and under continuous flow conditions. In general, yields obtained using the traditional batch process were higher than those observed when the reaction was performed under flow conditions. However, short reaction times, higher productivity and higher space time yields were observed when a flow system process was employed. Preliminary DFT calculations were also performed in order to elucidate the mechanism of the reaction.
- Abubakar, Said Said,Benaglia, Maurizio,Rossi, Sergio,Annunziata, Rita
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- Silver-mediated radical aryltrifluoromethylthiolation of activated alkenes by S-trifluoromethyl 4-methylbenzenesulfonothioate
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Herein, we describe the preparation of trifluoromethylthiol-substituted oxindoles by silver-mediated aryltrifluoromethylthiolation of activated alkenes, using S-trifluoromethyl 4-methylbenzenesulfonothioate as a F3CS radical source and showing that the reagent availability, mild conditions, and broad functional group compatibility of this transformation make it a viable alternative strategy of constructing Csp3–SCF3 bonds.
- Zhao, Xia,Yang, Bo,Wei, Aoqi,Sheng, Jianqiao,Tian, Miaomiao,Li, Quan,Lu, Kui
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p. 1719 - 1722
(2018/04/02)
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- Trifluoromethylthiolation of Unsymmetrical λ3-Iodane Derivatives: Additive-Free, Selective and Scalable Introduction of the SCF3 Group
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The reaction of copper trifluoromethyl sulfide with diaryliodonium salts provides a straightforward pathway for the synthesis of aryl trifluoromethyl thioethers under mild reaction conditions and within short reaction times. High chemoselectivity was achieved by using mesityl as a leaving group. A large range of novel [(het)aryl](mesityl)iodonium salts underwent this reaction under the optimized conditions to give the desired products in moderate to good yields.
- Nikolaienko, Pavlo,Yildiz, Tülay,Rueping, Magnus
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supporting information
p. 1091 - 1094
(2016/03/05)
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- Trifluoromethylthiolation reagent and its preparation method and use in asymmetric trifluoromethylthiolation reaction
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The invention discloses a trifluoromethylthiolation reagent and its preparation method and use in an asymmetric trifluoromethylthiolation reaction. The trifluoromethylthiolation reagent is prepared from commercial silver fluoride, dibenzenesulfonimide and t-butyl hypochlorite as basic raw materials through mixing. The preparation method has short reaction steps, operation easiness and high yield. The novel trifluoromethylthiolation reagent has stable chemical properties, is environmentally friendly and is convenient for storage. The trifluoromethylthiolation reagent has high activity in an asymmetric trifluoromethylthiolation reaction and has a wide application prospect in many organic reactions.
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Page/Page column 5
(2016/10/10)
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- A trifluro sulfur base copper (I) and sulfur base silver trifluoromethane (I) method for the preparation of
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The invention belongs to the technical field of trifluoromethyl sulfide reagent preparation, and particularly relates to a preparation method of copper trifluoromethyl sulfide (I) and silver trifluoromethyl sulfide (I). The method comprises the following steps: using lower-molecular nitrile as a reaction solvent, cuprous copper salt or cuprous silver salt and sodium trifluoromethanesulfonate as raw materials, then adding an organic phosphorus reducing agent, carrying out a sufficient stirring reaction under certain temperature and nitrogen environment, and after the reaction reaches the end point, carrying out the separation purification steps such as filtering, suction, washing and recrystallization to obtain the copper trifluoromethyl sulfide (I) or silver trifluoromethyl sulfide (I). The method is mild in reaction condition, high in operability and low in raw material cost; and moreover, the utilization rate and product yield of the metal element copper or silver are greatly improved, the technological process is short, the reaction scale is easy to enlarge, the product separation is simple, and the method has the advantage of being suitable for industrial production.
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Paragraph 0039; 0040
(2017/03/25)
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- N -Trifluoromethylthiolated Sulfoximines
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Air- and moisture-stable N-trifluoromethylthio sulfoximines have been prepared from N-H-sulfoximines via the corresponding N-Br derivatives in excellent yields. The two-step process starts with an easy-to-perform bromination at the sulfoximine nitrogen, followed by a reaction with silver trifluoromethanethiolate. A one-pot reaction sequence allows difficult to prepare products to be obtained.
- Bohnen, Christian,Bolm, Carsten
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supporting information
p. 3011 - 3013
(2015/06/30)
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- Direct trifluoromethylthiolation of unactivated C(sp3)-H using silver(I) trifluoromethanethiolate and potassium persulfate
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A practical and efficient method for the direct trifluoromethylthiolation of unactivated C(sp3)-H bonds by AgSCF3/K2S2O8 under mild conditions is described. The reaction has a good functional-group tolerance and good selectivity. Initial mechanistic investigations indicate that the reaction may involve a radical process in which K2S2O8 plays key roles in both the activation of the C(sp3)-H bond and the oxidation of AgSCF3.
- Wu, Hao,Xiao, Zhiwei,Wu, Junhui,Guo, Yong,Xiao, Ji-Chang,Liu, Chao,Chen, Qing-Yun
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supporting information
p. 4070 - 4074
(2015/03/30)
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- N-trifluoromethylthiosaccharin: An easily accessible, shelf-stable, broadly applicable trifluoromethylthiolating reagent
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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.
- Xu, Chunfa,Ma, Bingqing,Shen, Qilong
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supporting information
p. 9316 - 9320,5
(2014/10/15)
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- Direct trifluoromethylthiolation of alcohols under mild reaction conditions: Conversion of R-OH into R-SCF3
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A direct process for the trifluoromethylthiolation of allylic and benzylic alcohols under mild conditions has been developed. A wide range of free alcohols underwent nucleophilic substitution in the presence of stable CuSCF3 and BF3·Et2O to give the corresponding products in good to excellent yields.
- Nikolaienko, Pavlo,Pluta, Roman,Rueping, Magnus
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supporting information
p. 9867 - 9870
(2014/08/18)
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- An electrophilic hypervalent iodine reagent for trifluoromethylthiolation
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Sulfur and friends: A new electrophilic hypervalent iodine reagent 1 has been developed for direct trifluoromethylthiolation. A variety of nucleophiles, including β-ketoesters, aldehydes, amides, aryl or vinyl boronic acids, and alkynes, reacted with 1 under mild conditions to give the corresponding trifluoromethylthiolated compounds in good to excellent yields.
- Shao, Xinxin,Wang, Xueqiang,Yang, Tao,Lu, Long,Shen, Qilong
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supporting information
p. 3457 - 3460
(2013/04/24)
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