- Method for synthesizing nitro (hetero) aromatic hydrocarbon
-
The invention discloses a method for synthesizing nitro (hetero) aromatic hydrocarbon, and belongs to the field of organic synthesis. According to the method, simple (hetero) aromatic hydrocarbon is taken as an initial raw material and is stirred and reacted in an organic solvent at 40-100 DEG C under the action of a nitration reagent, a lewis acid catalyst and protective gas, and nitro (hetero) aromatic hydrocarbon can be obtained. The method provided by the invention has the advantages of cheap and easily available raw materials, mild reaction conditions, simple preparation process, good chemical selectivity, wide substrate application range, easy amplification and the like, has great application potential, and lays a good foundation for industrial production.
- -
-
Paragraph 0082-0084; 0088-0090
(2022/04/08)
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- Kilogram-Scale Preparation of the Easily Available, Low-Cost Electrophilic Trifluomethylating Reagent YlideFluor
-
A kilogram-scale process for the preparation of a potentially broadly applicable electrophilic trifluoromethylating reagent, (trifluoromethyl)(4-nitrophenyl)bis(carbomethoxy)methylide (YlideFluor), was reported. The reagent was prepared in three steps from a cheap, commercially available starting material, and the price of the reagent is estimated to be as low as $1.5/g. Application of the reagent in the preparation of trifluoromethylated derivatives of two drug molecules in the gram scale was demonstrated.
- Yao, Ruichao,Ling, Yijing,Chen, Wenbo,Lu, Long,Shen, Qilong
-
p. 299 - 306
(2022/02/10)
-
- Transition-Metal-Free Synthesis of Aryl Trifluoromethyl Thioethers through Indirect Trifluoromethylthiolation of Sodium Arylsulfinate with TMSCF3
-
Herein, we report an indirect trifluoromethylthiolation of sodium arylsulfinates. This transition-metal-free reaction significantly provides an environmentally friendly and practical synthetic method for aryl trifluoromethyl thioethers using commercial Ruppert-Prakash reagent TMSCF3. This approach is also a potential alternative to the current industrial production method owing to facile substrates, excellent functional group compatibility, and operational simplicity.
- Zheng, Changge,Jiang, Chao,Huang, Shuai,Zhao, Kui,Fu, Yingying,Ma, Mingyu,Hong, Jianquan
-
supporting information
p. 6982 - 6986
(2021/09/08)
-
- Rational Design and Development of Low-Price, Scalable, Shelf-Stable and Broadly Applicable Electrophilic Sulfonium Ylide-Based Trifluoromethylating Reagents
-
The development of two highly reactive electrophilic trifluoromethylating reagents (trifluoromethyl)(4-nitrophenyl)bis(carbomethoxy)methylide (1g) and (trifluoromethyl)(3-chlorophenyl)bis(carbomethoxy)methylide (1j) through structure-activity study was described. Under mild conditions, reagent 1g reacted with β-ketoesters and silyl enol ethers to give α-trifluoromethylated-β-ketoesters or α-trifluoromethylated ketones in high yields. In addition, reagent 1g could serve as a trifluoromethyl radical for a variety of trifluoromethylative transformations under visible light irradiation, including radical trifluoromethylation of electron-rich indoles and pyrroles and sodium aryl sulfinates as well as trifluoromethylative difunctionalization with styrene derivatives. On the other hand, as a complimentary, under reductive coupling conditions, reagent 1j reacted with a variety of (hetero)aryl iodides for the formation of trifluoromethylated (hetero)arenes.
- Ge, Hangming,Ling, Yijing,Liu, Yafei,Lu, Long,Shen, Qilong
-
p. 1667 - 1682
(2021/05/28)
-
- Synthetic method of aryltrifluoromethyl sulfide
-
The invention provides a synthesis method of an aryltrifluoromethyl sulfide compound, which comprises the following steps: mixing aryl halide, silver trifluoromethane mercaptide, a copper salt catalyst, a nitrogen-containing organic ligand and an organic solvent, and stirring at 20-120 DEG C to react for 1-60 hours, so that after the reaction is finished, the aryl trifluoromethyl thioether compound is generated. The method has the advantages of cheap and easily available raw materials, mild reaction conditions, good substrate universality, high yield, suitability for industrial application and the like.
- -
-
Paragraph 0040-0044
(2021/06/12)
-
- Electrochemical Trifluoromethylation of Thiophenols with Sodium Trifluoromethanesulfinate
-
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.
- Zhu, Xing-Xing,Wang, Huai-Qin,Li, Chen-Guang,Xu, Xiao-Lan,Xu, Jun,Dai, Jian-Jun,Xu, Hua-Jian
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p. 16114 - 16120
(2021/02/03)
-
- NITRATION
-
The present invention relates to a process for preparing a nitrated compound, comprising the step of reacting a compound (A) comprising at least one substituted or unsubstituted aromatic or heteroaromatic ring, wherein said heteroaromatic ring comprises at least one heteroatom selected from the group consisting of oxygen, sulfur, phosphor, selenium and nitrogen, with a compound of formula (I) wherein Y is selected from the group consisting of hydrogen and nitro.
- -
-
Page/Page column 36; 37; 47; 66-67
(2020/05/28)
-
- Enhancement of Benzothiazoles as Pteridine Reductase-1 Inhibitors for the Treatment of Trypanosomatidic Infections
-
2-Amino-benzo[d]thiazole was identified as a new scaffold for the development of improved pteridine reductase-1 (PTR1) inhibitors and anti-trypanosomatidic agents. Molecular docking and crystallography guided the design and synthesis of 42 new benzothiazoles. The compounds were assessed for Trypanosoma brucei and Leishmania major PTR1 inhibition and in vitro activity against T. brucei and amastigote Leishmania infantum. We identified several 2-amino-benzo[d]thiazoles with improved enzymatic activity (TbPTR1 IC50 = 0.35 μM; LmPTR1 IC50 = 1.9 μM) and low μM antiparasitic activity against T. brucei. The ten most active compounds against TbPTR1 were able to potentiate the antiparasitic activity of methotrexate when evaluated in combination against T. brucei, with a potentiating index between 1.2 and 2.7. The compound library was profiled for early ADME toxicity, and 2-amino-N-benzylbenzo[d]thiazole-6-carboxamide (4c) was finally identified as a novel potent, safe, and selective anti-trypanocydal agent (EC50 = 7.0 μM). Formulation of 4c with hydroxypropyl-β-cyclodextrin yielded good oral bioavailability, encouraging progression to in vivo studies.
- Linciano, Pasquale,Pozzi, Cecilia,Iacono, Lucia Dello,Di Pisa, Flavio,Landi, Giacomo,Bonucci, Alessio,Gul, Sheraz,Kuzikov, Maria,Ellinger, Bernhard,Witt, Gesa,Santarem, Nuno,Baptista, Catarina,Franco, Caio,Moraes, Carolina B.,Müller, Wolfgang,Wittig, Ulrike,Luciani, Rosaria,Sesenna, Antony,Quotadamo, Antonio,Ferrari, Stefania,P?hner, Ina,Cordeiro-Da-Silva, Anabela,Mangani, Stefano,Costantino, Luca,Costi, Maria Paola
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p. 3989 - 4012
(2019/05/06)
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- A process for converting substituted phenyl diazonium salts into [(trifluoromethyl)thio]benzene
-
The invention discloses a synthetic method of [(trifluoromethyl)thio]benzene compounds, particularly a method for converting substituted phenyl diazonium salts into [(trifluoromethyl)thio]benzene. Themethod comprises the following steps: under white light
- -
-
Paragraph 0102-0109
(2019/12/02)
-
- Method for producing substituted [(trifluoromethyl)thio]benzene from substituted aniline
-
The invention discloses a synthetic method of [(trifluoromethyl)thio]benzene compounds, particularly a method for preparing substituted [(trifluoromethyl)thio]benzene from substituted aniline. The method comprises the following steps: adding aromatic amine, a catalyst, tert-butyl nitrite and p-toluenesulfonic acid hydrate into a solvent; stirring the mixture for at least 5 minutes at the room temperature of 20-25 DEG C; then adding S-trifluoromethyl-4-methoxybenzenesulfonyl sulfate, and uniformly stirring the mixture; reacting the mixture under white light irradiation at the room temperature of 20-25 DEG C; determining the reaction ending time through spotting detection; after the reaction is finished, adding water for extraction; performing separation to obtain a liquid organic phase; drying the liquid organic phase with anhydrous Na2SO4; then removing a solvent; and performing rapid separation with column chromatography to obtain a [(trifluoromethyl)thio]benzene compound. The preparation method is mild in reaction condition, free of high-temperature and high-pressure reaction, safe in reaction condition and suitable for large-scale production and development.
- -
-
Paragraph 0076-0083
(2019/12/02)
-
- Visible-Light-Mediated Synthesis of Trifluoromethylthiolated Arenes
-
The visible-light-mediated synthesis of trifluoromethylthiolated arenes in the presence of ruthenium-based photocatayst under mild reaction conditions is reported. The trifluoromethylthiolated arenes are obtained using the shelf-stable reagent trifluoromethyl toluenethiosulfonate at room temperature. The reaction proceeds selectively and does not require the presence of any additive. A mechanism is proposed based on the obtained results of EPR as well as luminescence.
- Ghiazza, Clément,Monnereau, Cyrille,Khrouz, Lhoussain,Billard, Thierry,Tlili, Anis
-
supporting information
p. 2865 - 2870
(2019/07/09)
-
- Chalcogen OCF3 Isosteres Modulate Drug Properties without Introducing Inherent Liabilities
-
The synthesis of SCF3 as well as SeCF3 isosteres of two OCF3-containing drugs was achieved through visible light and copper-catalyzed processes. Herein, we show that chalcogen replacement modulates physicochemical and ADME properties without introducing intrinsic liabilities. The SCF3 and SeCF3 groups are more lipophilic than their oxygen counterpart; however, microsomal stability is unchanged, indicating that these molecular changes may be beneficial for in vivo half-life. Enabled by modern synthetic methods, we present the chalcogen-CF3 groups as potential key players for future fluorinated pharmaceuticals.
- Ghiazza, Clément,Billard, Thierry,Dickson, Callum,Tlili, Anis,Gampe, Christian M.
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supporting information
p. 1586 - 1589
(2019/08/26)
-
- Copper(I)-promoted trifluoromethylthiolation of arenediazonium salts with AgSCF3
-
An efficient method for trifluoromethylthiolation of arenediazonium salts has been developed in mild conditions with a stable and convenient AgSCF3. It provides a straightforward and convenient way for the synthesis of trifluoromethylthiolated compound from diazonium salts in moderate to good yields.
- Zheng, Changge,Liu, Yang,Hong, Jianquan,Huang, Shuai,Zhang, Wei,Yang, Yupeng,Fang, Ge
-
p. 1404 - 1407
(2019/05/01)
-
- Metal-free trifluoromethylthiolation of arenediazonium salts with Me4NSCF3
-
A metal-free entry to the pharmaceutically meaningful substrate class of trifluoromethyl thioethers has been developed starting from widely available arenediazonium salts and commercially available Me4N+SCF3?. This reaction proceeds within one hour at 0 °C and is applicable to a wide range of functionalized substrates.
- Bertoli, Giulia,Exner, Benjamin,Evers, Mathies V.,Tschulik, Kristina,Goo?en, Lukas J.
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p. 132 - 136
(2018/04/05)
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- Radical Aromatic Trifluoromethylthiolation: Photoredox Catalysis vs. Base Mediation
-
Trifluoromethyl aryl sulfides (Ar-SCF3) constitute highly attractive building blocks due to their exceptional lipophilicity and chemical properties. Related protocols of radical aromatic trifluoro-methylthiolation of arenediazonium salts were developed that are based on the facile generation of intermediate aryl radicals. Their reactions with commercial F3CS-SCF3 under very mild conditions afforded a diverse set of Ar-SCF3 (3]Cl2} with the weak base-mediated dark reaction documented higher synthetic efficiency of the former but higher operational simplicity of the latter strategy.
- Koziakov, Denis,Majek, Michal,Jacobi von Wangelin, Axel
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supporting information
p. 6722 - 6725
(2017/12/07)
-
- A concise and convenient synthesis of 4-(trifluoromethylthio)aniline
-
4-(Trifluoromethylthio)aniline, a key agricultural intermediate, can be synthesized from 4-nitrobromobenzene. First 4-nitrothioanisole was obtained by the methylthiotriazine of 4-nitrobromobenzene with sodium salt of methyl mercaptan in the presence of phase-transfer catalyst in a 91.4 % yield; then 4-(trifuroromethylthio)nitrobenzene was produced through chlorination in a 83.7 % yield and fluorination in a 86.3 % yield; finally the hydrogenation in the presence of Pd/C can afford 4-(trifluoromethylthio)aniline with a 98 % yield.
- Gong, Shunze,Cai, Xinhong,Fu, Hao,Xu, Defeng
-
-
- Silver-catalyzed fluoroalkylation of thiols using fluoroalkanesulfinates
-
A practical sliver-catalyzed fluoroalkylation of aryl-, heteroaryl- and alkylthiols has been developed. The reaction has a good functional-group tolerance and excellent selectivity. A variety of stable and solid fluoroalkanesulfinates including di- and perfluoroalkanesulfinates can be employed. This methodology provides a straightforward and streamlined access to perfluoroalkylthiolated organic molecules. [Figure presented]
- Ma, Jing-jing,Liu, Qi-ran,Lu, Guo-ping,Yi, Wen-bin
-
supporting information
p. 113 - 117
(2017/01/03)
-
- Triphenylphosphine-Mediated Deoxygenative Reduction of CF3SO2Na and Its Application for Trifluoromethylthiolation of Aryl Iodides
-
We report herein a practical method for taming Langlois' reagent CF3SO2Na to generate CuSCF3 by a triphenylphospine-mediated deoxygenative reduction process. This chemistry highlights a novel utilization of the inherent CF3S skeleton of Langlois' reagent as a CF3S feedstock under mild conditions. The CuSCF3 intermediate generated by this protocol can react with a wide array of supporting ligands to furnish several air-stable [LCu(SCF3)] complexes as valuable trifluoromethylthiolating agents. In addition, the CuSCF3 intermediate can be directly employed for the trifluoromethylthiolation of (hetero)aryl iodides with operational simplicity and atomic efficiency. Efficient synthesis! A low cost method for the generation of CuSCF3 by a triphenylphospine-mediated deoxygenative reduction of Langlois' reagent (CF3SO2Na) has been developed (see scheme). This method can be applied for the convenient synthesis of a wide array of ligated and air-stable CuSCF3 complexes. Additionally, the CuSCF3 complexes generated in situ by this protocol were found to trifluoromethylthiolate (hetero)aryl iodides with high efficiency.
- Yang, Yi,Xu, Long,Yu, Siqi,Liu, Xiaoqiang,Zhang, Yu,Vicic, David A.
-
supporting information
p. 858 - 863
(2016/01/16)
-
- A 4-trifluoromethane method for the preparation of thio nitrobenzene
-
The invention provides a preparation method of 4-(trifluoromethylthio)nitrobenzene, which is implemented by reacting paranitroanisole with trifluoro-methanthiol at a temperature of 60-150 DEG C, so that 4-(trifluoromethylthio)nitrobenzene is obtained. Acc
- -
-
Paragraph 0021; 0022; 0023; 0024
(2016/11/17)
-
- 2-Diazo-1-phenyl-2-((trifluoromethyl)sulfonyl)ethan-1-one: Another Utility for Electrophilic Trifluoromethylthiolation Reactions
-
2-Diazo-1-phenyl-2-((trifluoromethyl)sulfonyl)ethan-1-one (diazo-triflone) (2) is not only a building block but also a reagent. In this study, diazo-triflone, which was originally used for the synthesis of β-lactam triflones as a trifluoromethanesulfonyl
- Huang, Zhongyan,Okuyama, Kenta,Wang, Chen,Tokunaga, Etsuko,Li, Xiaorui,Shibata, Norio
-
p. 188 - 191
(2016/07/11)
-
- Trifluoromethylthiolation of Unsymmetrical λ3-Iodane Derivatives: Additive-Free, Selective and Scalable Introduction of the SCF3 Group
-
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
-
p. 1091 - 1094
(2016/03/05)
-
- Sandmeyer-Type Trifluoromethylthiolation and Trifluoromethylselenolation of (Hetero)Aromatic Amines Catalyzed by Copper
-
Aromatic and heteroaromatic diazonium salts were efficiently converted into the corresponding trifluoromethylthio- or selenoethers by reaction with Me4NSCF3 or Me4NSeCF3, respectively, in the presence of catalytic amounts of copper thiocyanate. These Sandmeyer-type reactions proceed within one hour at room temperature, are applicable to a wide range of functionalized molecules, and can optionally be combined with the diazotizations into one-pot protocols.
- Matheis, Christian,Wagner, Victoria,Goossen, Lukas J.
-
supporting information
p. 79 - 82
(2016/01/25)
-
- Trifluoromethylation of thiophenols and thiols with sodium trifluoromethanesulfinate and iodine pentoxide
-
A selective and facile trifluoromethylation process for a wide range of thiophenols and thiols under metal free conditions has been developed using two simple and safe solids, sodium trifluoro-methanesulfinate and iodine pentoxide, via the radical process.
- Ma, Jing-Jing,Yi, Wen-Bin,Lu, Guo-Ping,Cai, Chun
-
p. 417 - 421
(2016/02/03)
-
- Copper-Catalyzed Trifluoromethylthiolation of Di(hetero)aryl-λ3-iodanes: Mechanistic Insight and Application to Synthesis of (Hetero)Aryl Trifluoromethyl Sulfides
-
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.
- Saravanan, Perumal,Anbarasan, Pazhamalai
-
supporting information
p. 3521 - 3528
(2016/01/25)
-
- Iron-Catalyzed Decarboxylation of Trifluoroacetate and Its Application to the Synthesis of Trifluoromethyl Thioethers
-
Nucleophilic CF3 has been generated by decarboxylation of potassium trifluoroacetate, arguably the most easy-to-handle, inexpensive, and sustainable source of trifluoromethyl groups. Simple iron(II) chloride catalyzes the decarboxylation as well as a subsequent trifluoromethylation of organothiocyanates, resulting in a straightforward synthesis of trifluoromethyl thioethers. The KCN byproduct is absorbed by iron(II) with formation of nontoxic potassium hexacyanoferrate. An analogous trifluoromethylation of aldehydes with trifluoroacetate underlines the synthetic potential of such iron-catalyzed decarboxylative trifluoromethylations.
- Exner, Benjamin,Bayarmagnai, Bilguun,Jia, Fan,Goossen, Lukas J.
-
supporting information
p. 17220 - 17223
(2016/01/25)
-
- Reactions of allyl alcohols and boronic acids with trifluoromethanesulfonyl hypervalent iodonium ylide under copper-catalysis
-
Trifluoromethylsulfinyl and trifluoromethylthio groups are both important substituents for pharmaceuticals, agrochemicals and functional materials. We herein report the trifluoromethylthiolation of allyl alcohols 2 with trifluoromethanesulfonyl hypervalent iodonium ylide 1 under copper catalysis to provide trifluoromethylsulfinyl compounds 3. Trifluoromethylthiolation of boronic acids 4 with 1 furnished trifluoromethylthio compounds 5.
- Arimori, Sadayuki,Takada, Masahiro,Shibata, Norio
-
supporting information
p. 19456 - 19459
(2015/11/27)
-
- Trifluoromethylthiolation of aryl iodides and bromides enabled by a bench-stable and easy-to-recover dinuclear palladium(I) catalyst
-
Abstract While palladium catalysis is ubiquitous in modern chemical research, the recovery of the active transition-metal complex under routine laboratory applications is frequently challenging. Described herein is the concept of alternative cross-coupling cycles with a more robust (air-, moisture-, and thermally-stable) dinuclear PdI complex, thus avoiding the handling of sensitive Pd0 species or ligands. Highly efficient C-SCF3 coupling of a range of aryl iodides and bromides was achieved, and the recovery of the PdI complex was accomplished via simple open-atmosphere column chromatography. Kinetic and computational data support the feasibility of dinuclear PdI catalysis. A novel SCF3-bridged PdI dimer was isolated, characterized by X-ray crystallography, and verified to be a competent catalytic intermediate. Pd double team: The cross-coupling enabled by an air-, moisture-, and thermally stable dinuclear PdI complex was explored. Highly efficient C-SCF3 coupling of a range of aryl iodides and bromides was achieved and the catalyst was recovered by simple column chromatography, thus highlighting its robustness and the possibility for catalyst recycling. Kinetic and computational data support the feasibility of dinuclear PdI catalysis.
- Yin, Guoyin,Kalvet, Indrek,Schoenebeck, Franziska
-
supporting information
p. 6809 - 6813
(2015/06/08)
-
- A mild and fast photocatalytic trifluoromethylation of thiols in batch and continuous-flow
-
S-CF3 bonds are important structural motifs in various pharmaceutical and agrochemical compounds. However, their preparation remains a major challenge in synthetic organic chemistry. Here, we report the development of a mild and fast photocatalytic trifluoromethylation of thiols. The combination of commercially available Ru(bpy)3Cl2, visible light and inexpensive CF3I gas proved to be an efficient method for the direct trifluoromethylation of thiols. The protocol is demonstrated on a wide range of aromatic, hetero-aromatic and aliphatic substrates in both batch and continuous microflow (32 examples, 52-98% yield). Process intensification through continuous microflow application resulted in a 15-fold increase in production rate (0.25 mmol min-1) due to improved gas-liquid mass transfer, enhanced irradiation as well as convenient handling of the gaseous CF3 source. Furthermore, the efficiency of the flow process allowed to reduce the amount of CF3I (1.1 equivalent) to reach full conversion. This journal is
- Straathof, Natan J. W.,Tegelbeckers, Bart J. P.,Hessel, Volker,Wang, Xiao,Nol, Timothy
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p. 4768 - 4773
(2015/01/09)
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- Copper-catalyzed synthesis of aryl and alkyl trifluoromethyl sulfides using CF3SiMe3and Na2S2O3as -SCF3source
-
A universal and efficient Cu(I)-catalyzed synthesis of aryl and alkyl trifluoromethyl sulfides has been developed. In this catalytic system, S-aryl or S-alkyl sulfothioate (I or II) proved to be the key intermediate. Substrates bearing groups of I, Br, Cl, OTs, and OMs on the aryl carbon and no matter electron-withdrawing and electron-donating substitutions on the aromatic ring could afford good to excellent yields.
- Zhong, Wei,Liu, Xiaoming
-
supporting information
p. 4909 - 4911
(2014/12/10)
-
- An air-stable copper reagent for nucleophilic trifluoromethylthiolation of aryl halides
-
A series of copper(I) trifluoromethyl thiolate complexes have been synthesized from the reaction of CuF2 with Me3SiCF 3 and S8 (see scheme; Cu red, F green, N blue, S yellow). These air-stable complexes serve as reagents for the efficient conversion of a wide range of aryl halides into the corresponding aryl trifluoromethyl thioethers in excellent yields. Copyright
- Weng, Zhiqiang,He, Weiming,Chen, Chaohuang,Lee, Richmond,Tan, Davin,Lai, Zhiping,Kong, Dedao,Yuan, Yaofeng,Huang, Kuo-Wei
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supporting information
p. 1548 - 1552
(2013/03/13)
-
- A new method for the synthesis of trifluoromethylating agents-Diaryltrifluoromethylsulfonium salts
-
A new synthetic method has been developed to prepare diaryltrifluoromethylsulfonium salts from diaryldifluorosulfuranes by the action of Me3SiCF3/F-. This reaction is the transformation of nucleophilic trifluoro-methylating reagent into electrophilic one.
- Yagupolskii, Lev M.,Matsnev, Andrej V.,Orlova, Raisa K.,Deryabkin, Boris G.,Yagupolskii, Yurii L.
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p. 131 - 136
(2008/09/21)
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- Recent advances in electrophilic CF3-transfer using hypervalent iodine(III) reagents
-
The development of new methodologies for an efficient introduction of CF3 groups into complex molecules constitutes one of the most challenging tasks of modern organic chemistry. Recently, we reported the access to a new class of electrophilic CF3-transfer reagents based on hypervalent iodine. The versatile application of these reagents to C-centred nucleophiles, such as β-keto esters, silyl enol ethers and α-nitro esters, as well as to thiols and primary and secondary phosphines is described. Experiments with phenols afforded corresponding trifluomethylethers in very low yields. Schweizerische Chemische Gesellschaft.
- Kieltsch, Iris,Eisenberger, Patrick,Stanek, Kyrill,Togni, Antonio
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scheme or table
p. 260 - 263
(2009/04/07)
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- Selective oxidation and chlorination of trifluoromethylsulfide using trichloroisocyanuric acid in ionic liquid
-
A route to chemoselective oxidation and chlorination of aryltrifluoromethylsulfide using trichloroisocyanuric acid (TCCA) in ionic liquid, an efficiently O-methylation reaction and a reduction of nitro- to amido- in excellent yields have been developed.
- Tang, Ri-Yuan,Zhong, Ping,Lin, Qiu-Lian
-
p. 636 - 640
(2008/01/06)
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- Mild electrophilic trifluoromethylation of carbon- and sulfur-centered nucleophiles by a hypervalent iodine(III)-CF3 reagent
-
Inexpensive, recyclable, and activable: these are the features of a new mild electrophilic trifluoromethylation reagent that can be used to transfer a CF3 group to C-centered nucleophiles, such as β-keto esters and α-nitro esters, and to S-centered nucleophiles (see scheme). (Chemical Equation Presented).
- Kieltsch, Iris,Eisenberger, Patrick,Togni, Antonio
-
p. 754 - 757
(2007/10/03)
-
- Synthesis of aryl perfluoroalkyl sulfides from aromatic disulfides
-
Thermolysis of xenon(II) bis(perfluoroalkanecarboxylates) in the presence of diaryl disulfides occurs through the S-S bond cleavage to form dihalo-, halonitro-, and halodinitrophenyl perfluoroalkyl sulfides. The latter type of compounds was obtained for the first time. The main side process is the perfluoroalkylation of the aromatic ring.
- Sipyagin,Enshov,Kashtanov,Potemkin,Thrasher,Waterfeld
-
p. 420 - 434
(2007/10/03)
-
- Process of use in perfluoroalkyation and reactant for making use of this process
-
The subject-matter of the present invention is a process of use in perfluoroalkylation and a reactant for making use of this process. This process is defined in that it comprises a stage in which a material of formula RfH and a base (or a species capable of generating a base) are brought into contact, in a polar and anhydrous medium, with a substrate carrying at least one electrophilic functional group. Application to organic synthesis.
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-
-
- Trifluoromethylthiodediazoniation: A simple, efficient route to trifluoromethyl aryl sulfides
-
Copper(I) trifluoromethanethiolate reacts with a range of diazonium salts containing electron-withdrawing groups to give the corresponding trifluoromethyl aryl sulfides in high yield; it is also possible to carry out the diazotisation and trifluoromethylthiolation in one pot directly from the anilines.
- Adams, Dave J.,Goddard, Andrew,Clark, James H.,Macquarrie, Duncan J.
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p. 987 - 988
(2007/10/03)
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- Effective nucleophilic trifluoromethylation with fluoroform and common base
-
Common bases (alcoholate, dimsyl anion or amide) are able to deprotonate trifluoromethane to form a trifluoromethyl anion equivalent. In this reaction DMF plays a crucial role of stabilisation Trifluoromethyl aryl alcohols, ketones or sulfides can be obtained in good yields with the new reagent CF3H/Base/DMF.
- Russell, Jamie,Roques, Nicolas
-
p. 13771 - 13782
(2007/10/03)
-
- Preparation of trifluoromethyl sulfides or selenides from trifluoromethyl trimethylsilane and thiocyanates or selenocyanates
-
Trifluoromethyl sulfides (or selenides) are easily obtained in one pot at 0°C from thiocyanates (or selenocyanates), commercial trifluoromethyl trimethylsilane and catalytic amounts of tetrabutylammonium fluoride (TBAF).
- Billard, Thierry,Large, Sylvie,Langlois, Bernard R.
-
-
- A new simple access to trifluoromethyl thioethers or selenoethers from trifluoromethyl trimethylsilane and disulfides or diselenides
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Trifluoromethyl thioethers (or selenoethers) are easily obtained in one pot at 0°C from disulfides (or diselenides), commercial trifluoromethyl trimethyl silane and TBAF.
- Billard, Thierry,Langlois, Bernard R.
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p. 6865 - 6868
(2007/10/03)
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- Electrochemical initiation by sulfur dioxide of radical-chain trifluoromethylation processes of thiophenols with bromotrifluoromethane
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Sulfur dioxide may serve as an efficient catalyst for the electrochemical trifluoromethylation of thiophenols by Freon F13B1 (CF3Br), which enables implementation of trifluoromethylation in an energy-saving radical-chain regime. - Keywords: Electrochemical trifluoromethylation; Thiophenols; Radical-chain processes; Bromotrifluoromethane; Sulfur dioxide catalyst
- Koshechko, V. G.,Kiprianova, L. A.,Fileleeva, L. I.,Rozhkova, Z. Z.
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p. 277 - 278
(2007/10/02)
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- Nucleophilic trifluoromethylation of organic substrates using (trifluoromethyl)trimethylsilane in the presence of a fluoride anion. II. A convenient route to aryltrifluoromethyl-sulfides, - sulfoxides and -sulfones
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Aryltrifluoromethyl-sulfides, -sulfoxides and -sulfones can be prepared by trifluoromethylation of the corresponding arylsulfenyl, -sulfinyl and -sulfonyl halides using (trifluoromethyl)trimethylsilane in the presence of fluoride sources, such as TASF . - Keywords: Nucleophilic trifluoromethylation; (Trifluoromethyl)trimethylsilane; Fluoride anion; Aryltrifluoromethylsulfides; Aryltrifluoromethylsulfoxides; Aryltrifluoromethylsulfones
- Movchun, Valeria N.,Kolomeitsev, Alexander A.,Yagupolskii, Yurii L.
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p. 255 - 258
(2007/10/02)
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- Direct Trifluoromethylthiolation of Aryl Halides using Methyl Fluorosulfonyldifluoroacetate and Sulfur
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In the presence of S8 and copper(I) iodide, methyl fluorosulfonyldifluoroacetate 1 reacts with aryl halides 2 in hexamethylphosphoramide (HMPA) or N-methylpyrrolidinone (NMP) at 100-110 deg C to give the corresponding trifluoromethylthiolated derivatives 3 in good yields.
- Chen, Qing-Yun,Duan, Jian-Xing
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p. 918 - 919
(2007/10/02)
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- A new convenient method for the synthesis of perfluoroalkylarylsulfides
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Methylviologen has been shown to be an effective homogeneous catalyst in the perfluoroalkylation of thiophenols with perfluoroalkyliodides.
- Koshechko,Kiprianova,Fileleeva
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p. 6677 - 6678
(2007/10/02)
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- PREPARATION AND FLUORINATION OF ARYLTRIFLUOROMETHYLSULPHONES
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A series of chloro- and nitrophenyl trifluoromethyl sulphides and sulphones have been synthesised from the corresponding aryl halides .The fluorination of these compounds by tetra-n-butyl ammonium fluoride and potassium fluoride has been investigated.Our results show that generally they are more susceptible to fluorodenitration than fluorodechlorination.
- Beaumont, Andrew J.,Clark, James H.
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p. 295 - 300
(2007/10/02)
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- THE INTRODUCTION OF SCF3 INTO AROMATIC SUBSTRATES USING CuSCF3 AND ALUMINA-SUPPORTED CuSCF3
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Trifluoromethylthiocopper(I) has been readily prepared from the silver analogue, using a metathetical reaction with copper(I) bromide.Homogeneous CuSCF3 and the supported reagent CuSCF3-alumina have been compared in their reactivity towards aryl iodides, in order to form trifluoromethylaryl sulphides in good yields.
- Clark, James H.,Craig, W. Jones,Kybett, Adrian P.,McClinton, Martin A.,Miller, Jack M.,et al.
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p. 249 - 255
(2007/10/02)
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- FLUORO(TRIFLUOROMETHYL)ARYLSULFONIUM AND (TRIFLUOROMETHYL)DIARYLSULFONIUM SALTS
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The oxygen atoms in aryl trifluoromethyl sulfoxides are substituted by fluorine during the action of the SF3(1+)*BF4(1-) and SF3(1+)*SbF6(1-) complexes.Fluoro(trifluoromethyl)arylsulfonium and (trifluoromethyl)diarylsulfonium salts were synthesized.The la
- Yagupol'skii, L. M.,Kondratenko, N. V.,Timofeeva, G. N.
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p. 103 - 106
(2007/10/02)
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- PREPARATION OF BROMODIFLUOROMETHYL SULFIDE AND ITS CONVERSION TO TRIFLUOROMETHYL SULFIDE
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Bromodifluoromethyl sulfides are prepared by the reaction of mercaptides with CF2BrX (x=Br,Cl).And treatment of bromodifluoromethyl sulfides with various inorganic fluorides produced trifluoromethyl sulfides.
- Suda, Minoru,Hino, Chiaki
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p. 1997 - 2000
(2007/10/02)
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- Substituted amino acids
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Esters and thiolesters of amino acids, intermediates therefor, synthesis thereof, and the use of said esters and thiolesters and compositions for the control of pests.
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